Part 06
Business Continuity Small Teams
Speaker 1: [warmly] Imagine the espresso machine dies right before opening. For lean
teams, a system outage feels just as disruptive—orders pile up, schedules slip, and that
one frustrated customer tells ten friends.
Speaker 2: And because we wear so many hats, the person who knows how to restart
the point-of-sale app might be on a hiking trip. Suddenly a tiny knowledge gap becomes
a revenue gap.
Speaker 1: Continuity planning simply maps the moments that matter most so we can
keep payroll, customer conversations, and compliance humming.
Speaker 2: Think of it as operational insurance: a few hours building a plan today saves
weeks of apologizing later.
Speaker 1: [thoughtfully] Let’s look at Sarah’s meal-prep shop. She and three
teammates rely on Square, Google Drive, and a single Wi-Fi router to organize Saturday
market orders.
Speaker 2: The night before their busiest event, the ISP had a regional outage. No Wi-Fi
meant Square terminals froze and the shared spreadsheet refused to load.
Speaker 1: No one had printed recipes or enabled offline card mode, so dawn was spent
calling customers, rewriting lists, and chasing a hotspot.
Speaker 2: They made it to the market, but refunds and rush deliveries erased profits.
That scramble is why we build continuity muscle now.
Speaker 1: Every continuity plan starts with a simple impact analysis. Which systems do
customers notice first when they wobble, and how long before trust erodes?
Speaker 2: Then we set recovery time and recovery point objectives—the windows that
tell us when to switch to backups or a manual workaround.
Speaker 1: We capture those decisions inside runbooks so anyone on the team can
open a document and follow the breadcrumbs during an outage.
Speaker 2: [encouragingly] Finally, we rehearse. Tabletop drills and restore tests in
calm weather keep the plan aligned with reality and uncover gaps before customers do.
Speaker 1: [pragmatically] Backups are only useful if they actually restore. Start by
automating daily snapshots for slow-changing files and point-in-time recovery for
transactional data.
Speaker 2: Then keep at least one copy away from your primary environment—another
cloud region, an encrypted drive at the office, or a trusted backup service.
Speaker 1: Every quarter, boot those backups in a staging space to confirm they open,
sync, and connect the way you expect.
Speaker 2: Document retention rules and assign two people to each workflow so
vacations, turnover, or illness never leave you guessing when a restore clock is ticking.
Speaker 1: When the lights flicker, communication is half the battle. Draft status posts,
customer emails, and investor updates while you’re calm so you’re not wordsmithing
mid-crisis.
Speaker 2: Each template should say who hits “send,” who approves the language, and
how often updates go out until things are stable.
Speaker 1: Pair plain-language summaries for customers with tighter technical timelines
for partners or regulators who need the gritty details.
Speaker 2: [reassuringly] Keep a SMS or phone tree for the people who must hear from
you directly, and archive final messages as training material once the dust settles.
Speaker 1: Vendors can be both lifelines and single points of failure. Start by listing
every external tool—payments, scheduling, shipping—and rating the impact if each
goes dark for a day.
Speaker 2: Capture the safety nets you already have: offline modes, mobile hotspots, a
secondary domain, or even a paper form that keeps sales moving.
Speaker 1: Reach out to vendors now about emergency credits or expedited support,
and document account numbers, contacts, and contract clauses in one accessible spot.
Speaker 2: [confidently] With that prep, you can pivot to manual workarounds or a
backup provider before customers notice a wobble.
Speaker 1: [methodically] Here’s a lightweight checklist to keep momentum. First,
inventory the services, data stores, and processes that keep revenue flowing and note
the owners.
Speaker 2: Next, jot down recovery targets beside each item and link the
evidence—backup logs, alternative workflows, or supplier agreements—that prove you
can meet them.
Speaker 1: Refresh contact trees, vendor lists, and message templates every quarter so
names, numbers, and language stay accurate.
Speaker 2: Schedule restore drills and tabletop sessions on the shared calendar, and
after each exercise capture lessons learned and update the plan before the memory
fades.
Speaker 1: Continuity leadership in small organizations rarely looks like a full-time role.
It might be a fractional CTO, an operations generalist, or the compliance lead who loves
tidy processes.
Speaker 2: Entry points can be support engineers volunteering to run incident response,
founders doubling as IT admins, or a managed service provider on retainer.
Speaker 1: The stars share three traits: steady decision-making, a documentation-first
mindset, and empathy for teammates juggling anxious customers.
Speaker 2: [optimistically] Grow that bench by cross-training finance, HR, and customer
success leads so the business keeps resilience top of mind as headcount scales.
Speaker 1: [calmly] The through-line here is simple: preparedness beats heroics.
Speaker 2: When backups, communication scripts, and vendor contacts are
documented and practiced, a 2am outage becomes a routine you already know.
Speaker 1: Customers feel cared for, teammates avoid burnout, and the business keeps
its promises even when technology misbehaves.
Speaker 2: And when regulators or investors ask for evidence, you already have
timelines, decisions, and test logs at your fingertips.
Speaker 1: That’s the payoff for carving out a few focused hours now—you earn the
confidence to keep serving people no matter what the weekend throws at you.
# Narrative Outline — Business Continuity for Small Teams
## Tasks
- [ ] Explain backups, incident communication templates and vendor redundancy basics.
- [ ] Use the "night our MongoDB crashed" story to anchor the lesson.
- [ ] Prompt learners to draft a lightweight continuity checklist.
## Notes
- Cover continuity planning essentials with the MongoDB outage anecdote.
Capstone Red Team Exercise
Speaker 1: [energized] This capstone is your chance to break things safely. We
pressure-test a 15-person startup without touching their production stack.
Speaker 2: The goal is to practice red-team curiosity, blue-team calm and facilitation
skills that keep stakeholders engaged instead of defensive.
Speaker 1: We finish by translating every insight into a maturity score and a backlog
leaders can actually fund.
Speaker 2: And along the way we highlight the cross-functional cast—fractional CTOs,
success managers, ops leads—who make improvements stick.
Speaker 1: Our scenario centers on Sarah's marketplace startup—fifteen people
juggling weekly releases, contractors and a global customer base.
Speaker 2: Their stack is modern but stitched together: managed Kubernetes, GitHub
Actions, Google Workspace, Notion, HubSpot, Stripe.
Speaker 1: They lean on a fractional SOC, an MSP for laptops and an offshore labeling
partner, so third-party trust boundaries really matter.
Speaker 2: Pain points are already on the table: ad-hoc onboarding, shadow SaaS
creep, almost no incident rehearsal and compliance debt chasing them into every sales
call.
Speaker 1: We split into pods of five or six—red-team analysts, blue-team responders, a
business voice and a scribe.
Speaker 2: Ninety minutes goes fast, so the facilitator guards the timeboxes: twenty for
recon, thirty for the live drill, twenty-five to debrief, fifteen to prep the share-out.
Speaker 1: Injects keep everyone honest, but the tone stays curious, not accusatory.
Speaker 2: Everything you need lives in the shared workspace—architecture map, SaaS
inventory, contract snippets, customer personas—so no one is guessing.
Speaker 1: Phase one is pure recon. The red team maps assets, data flows and every
third-party touchpoint they can spot.
Speaker 2: We ask for the top three attack vectors—with evidence. Credential reuse?
Misconfigured S3 buckets? Vendor breach cascading into production?
Speaker 1: Each threat must tie back to business impact so sales, support and
engineering leaders understand the stakes.
Speaker 2: The scribe logs unanswered questions to keep momentum while still
capturing gaps for later homework.
Speaker 1: In phase two, the facilitator picks a scenario—maybe a compromised GitHub
token that poisons container images.
Speaker 2: Blue-team responders narrate how they'd spot it, contain it, communicate
with customers and loop in legal or finance.
Speaker 1: Injects keep tension high: a product launch collides with the incident, the
MSP contact is offline, the SOC queue is overflowing.
Speaker 2: We encourage teams to draft customer updates, board brief talking points
and even postmortem outlines while the adrenaline is still flowing.
Speaker 1: Debrief time means switching to evidence-based grading. Each pod scores
people, process, technology and governance on a one-to-five scale.
Speaker 2: We tie every score to artifacts—outdated runbooks, missing tabletop
cadence, a single approver on critical releases.
Speaker 1: Then we prioritize the backlog: lightning fixes like closing MFA gaps,
medium-term plays like renegotiating vendor contracts, strategic bets like observability
upgrades.
Speaker 2: Finally, we capture what leadership must unlock—budget, headcount, or
policy—to sustain momentum.
Speaker 1: The maturity model keeps scoring consistent. Level one is ad hoc—heroics,
no playbooks, barely any logging.
Speaker 2: Level two is emerging: some runbooks, partial MFA, retros that happen but
rarely translate into change.
Speaker 1: Level three is scaling—quarterly tabletops, defined SLAs, vendor scorecards,
baseline observability.
Speaker 2: Level four is measured with automated controls, resilience OKRs and real
budgets; level five is optimized, where purple teaming and partner collaboration are
business as usual.
Speaker 1: Each pod leaves with tangible artifacts: a risk map, attack narrative,
maturity scores and a remediation backlog with owners and timelines.
Speaker 2: Visuals help—journey maps, swimlanes, heat maps make executive
conversations concrete rather than theoretical.
Speaker 1: We use a "start, stop, continue" debrief to surface cultural shifts alongside
technical fixes.
Speaker 2: And everyone closes with a commitment statement so momentum carries
beyond the classroom.
Speaker 1: The exercise spotlights multiple roles: fractional CTOs, security leads,
product managers, customer success managers, operations analysts.
Speaker 2: Entry points vary—support engineers stepping into incident command,
consultants shifting into virtual CISO work, operations generalists owning vendor
programs.
Speaker 1: The standout traits are facilitation under pressure, systems thinking,
empathy for non-technical teammates and curiosity about adversary tradecraft.
Speaker 2: Nail this capstone and you're charting a path toward security program
management, resilience leadership or platform engineering direction.
Speaker 1: The takeaway is simple: rehearsal builds muscle memory faster than policy
memos ever could.
Speaker 2: By red-teaming Sarah's startup together, we generate evidence-backed
maturity scores and a sequenced roadmap that leaders can champion.
Speaker 1: Treat the session like prep for the next diligence meeting—you want
answers ready before investors or auditors ask.
Speaker 2: And the real win is renewed shared accountability before the inevitable
real-world incident arrives.
# Narrative Outline — Capstone: Red Team Your Friend's Startup
## Tasks
- [x] Design the group exercise to critique a sample startup toolchain.
- [x] Include steps for running a security incident drill for a 15-person team.
- [x] Show how to map Sarah's company onto the maturity model as part of the debrief.
## Notes
- Lay out the capstone group exercise structure and maturity model mapping activity
with concrete timelines, roles and deliverables.
Capstone Remediation Roadmap
Speaker 1: Welcome to the remediation roadmap workshop—the moment where all that
red-team adrenaline turns into a plan people will actually follow.
Speaker 2: Exactly, and we’re keeping it grounded in Sarah’s startup so you can see
how each idea plays out in a real company, not a textbook fantasy.
Speaker 1: By the end you’ll have a reusable template, plus a few jokes to disarm tense
stakeholders when the topic turns to breaches before breakfast.
Speaker 1: Let’s kick off with the “why.” Without a roadmap, all those red sticky notes
become that gym membership you bought in January—great intentions, zero
follow-through.
Speaker 2: And Sarah’s investors don’t care about sticky notes; they want to know
who’s fixing the unlogged database access and when it’ll be safe to brag about it in
board meetings.
Speaker 1: Stick with us and we’ll turn the chaos into sequenced, funded work everyone
can champion.
Speaker 1: Before we rush into solutions, consolidate every artifact from the drill—risk
rankings, quotes from the red team, that horrifying clip where customer support
browsed production.
Speaker 2: Right, the richer the inputs, the easier it is to answer executives later
without scrambling for context.
Speaker 1: Take a minute now to flag unanswered questions for the MSP, SOC or legal
folks so nothing slips between cracks once we leave the room.
Speaker 1: Let’s carve the backlog into Stabilise, Reinforce and Scale so the urgent
fixes don’t drown out the long-term bets.
Speaker 2: For Sarah that means Stabilise covers MFA and database access, Reinforce
adds automated backup testing, and Scale explores a SIEM pilot.
Speaker 1: Capture owners, collaborators and success metrics while you go—it saves so
many “who’s on this?” messages later.
Speaker 1: Scoring time. Rank impact, regulatory exposure, customer promises and
effort—don’t just default to “critical” for everything.
Speaker 2: Yeah, when everything is critical, nothing gets done. Ask what your most
skeptical investor would grill you on and let that sharpen the order.
Speaker 1: Capture the due diligence questions right beside the work so the finance or
legal follow-ups have a clear home.
Speaker 1: Let’s layer in time horizons—what lands in the first 30 days versus 60 or 90
so the plan feels achievable.
Speaker 2: In Sarah’s case the “30” bucket is the production database fix and MFA
clean-up, while the “60” bucket covers runbook refreshes and due diligence trackers.
Speaker 1: Exactly, and anything needing contracts or new tools probably lives in the
90-day lane so leaders see budget bumps coming.
Speaker 1: Ownership time—every item needs an executive sponsor, a delivery lead
and supporting squad, plus a ritual where status gets checked.
Speaker 2: Otherwise we’ve just made someone captain of a ship without handing them
the steering wheel, and Sarah’s team doesn’t have time for that.
Speaker 1: Build the communication plan now—think quick Loom updates,
investor-ready bullets and which customer advocates should preview changes.
Speaker 1: Now let’s talk risk communication—executives need a one-page story that
connects technical jargon to customer impact, cost and compliance.
Speaker 2: So for Sarah we highlight that the database exposure risks GDPR fines and
investor confidence, then pair it with the mitigation plan and price tag.
Speaker 1: Practice saying “We eliminated X risk this month; Y is next in line” so you
can answer “Are we safe?” without bluffing.
Speaker 1: Change management is where good plans go to live or die, so map the
stakeholders and what they secretly worry about.
Speaker 2: For example, engineering fears surprise workloads, support wants proof
customer comms won’t break, and finance wants to see cost avoidance.
Speaker 1: Meet them where they are with Loom explainers, office hours and training
so adoption beats compliance theater.
Speaker 1: Measurement keeps momentum, so set up a dashboard—even if it’s Google
Sheets—that tracks risk burn down, spend and blockers.
Speaker 2: Celebrate the green lights too; ring a Slack bell when Sarah’s team locks
down the prod database or crushes a diligence interview.
Speaker 1: And when something slips, log the lesson learned and next experiment so
you don’t lose trust with leadership.
Speaker 1: Reflection isn’t fluff—capturing surprises and broken assumptions shows
investors you’re learning, not just reacting.
Speaker 2: Let’s pose it to the room: what did Sarah’s team get wrong about vendor
coverage, and what support do they need to keep momentum?
Speaker 1: Encourage them to log those answers with the backlog so leadership sees
the human side of resilience work.
Speaker 1: Time to build—open the template and draft Sarah’s roadmap with five
concrete actions, metrics and a review date.
Speaker 2: Don’t forget a mini risk register entry and an executive summary paragraph;
those pieces make the homework instantly useful.
Speaker 1: We’ll circle the room, answer questions, and line up five-minute readouts for
next session—one risk retired, one still nagging, one follow-up call booked.
Speaker 1: Quick reminder on resources—you’ve got the backlog spreadsheet,
executive summary template and the risk register from earlier sessions.
Speaker 2: Plus links to ServiceNow, Jira or Linear examples, and the Part 5
communication plan so cadence rituals stay aligned.
Speaker 1: Bookmark them now; nothing kills momentum like hunting for a template
five minutes before an investor call.
Speaker 1: Let’s land the plane—a good roadmap keeps the capstone energy alive and
proves progress with evidence.
Speaker 2: Publish your draft within 48 hours, celebrate the first win loudly, and be
honest about the next big risk on deck.
Speaker 1: Do that and Sarah’s team—and yours—will keep improving long after the
exercise ends.
# Narrative Outline — Capstone: Remediation Roadmap
## Tasks
- [x] Prompt participants to generate due diligence questions tailored to their startup
scenario.
- [x] Guide teams in assembling a take-home remediation roadmap.
- [x] Define reflection questions to close the capstone.
## Notes
- Plan the take-home remediation roadmap and reflection prompts for the capstone.
- Include slides on risk communication, change management, measurement and
available templates to support non-technical learners.
Cloud Vs On Premise Decisions
Speaker 1: When founders say "we need to pick cloud or on-prem," they're really
deciding where compute, storage, networking and identity will live.
Speaker 2: Exactly—and the answer can differ per layer. SaaS keeps you hands-off,
PaaS gives you guardrails, and IaaS is the build-it-yourself toolbox.
Speaker 1: Add in acronyms like SRE and questions about colocation versus true
on-prem, and it's easy to lose clarity. Start by mapping what customers expect, what
regulators demand and what your team can realistically operate.
Speaker 1: In the first twelve months, speed beats everything—use the managed
services that let you ship without hiring SREs.
Speaker 2: Right, because you literally can't afford to hire SREs yet. A senior SRE costs
$180k+ in salary alone, before tooling or on-call bonuses.
Speaker 1: By year two, finance wants predictability. That's when you compare
reserved cloud instances to colocated gear and understand your utilisation curves.
Speaker 2: And as you approach Series B, you revisit the architecture—maybe customer
data has to stay in-region, or latency targets push you toward an edge footprint.
Speaker 1: Serverless is a gift when you're still searching for product-market fit. No
patching, no capacity planning—just deploy functions.
Speaker 2: And the bill stays tiny while usage is modest. That food delivery beta with a
hundred testers might cost $50 a month instead of thousands in idle servers.
Speaker 1: The trade-off is vendor coupling, so script periodic API reviews, export
datasets and rehearse migrations so an exit option stays alive.
Speaker 1: Managed services sit in the middle—they remove toil but still let you shape
the environment.
Speaker 2: That serverless approach we just mentioned? Managed platforms are the
next step when you need more knobs without rebuilding plumbing.
Speaker 1: Think managed Kubernetes, relational databases or desktop-as-a-service, all
defined through infrastructure as code so the setup is reproducible.
Speaker 2: Just remember: even if the provider handles hardware, your team still
carries the pager for misconfigurations and app bugs.
Speaker 1: Containers promise cost control, but they demand engineering maturity.
Speaker 2: Without observability, vulnerability scanning, hardened base images and a
registry strategy, you're just moving risk from AWS into your unfinished build pipeline.
Speaker 1: Treat the platform like a product—budget time for upgrades, policy
automation and yes, the coffee-machine moment when you realise you built something
no one can maintain.
Speaker 1: Startup credits are powerful if you plan ahead—AWS Activate, Azure for
Startups and Google Cloud can subsidise six figures of usage.
Speaker 2: Make a burn-down chart of credits versus forecasted spend, and remember
AWS Activate credits expire after two years or once you raise a Series A.
Speaker 1: Pair those credits with SaaS products that have generous free tiers so you
don't waste credits on commodity tooling—and avoid the "we thought it was still free"
surprise invoice.
Speaker 1: Before you jump into containers, ask whether your CI/CD actually enforces
testing and security scanning today.
Speaker 2: Also, who is on the hook for 24/7 monitoring? A three-person team cannot
sustain night shifts and keep product velocity high.
Speaker 1: If your "on-call rotation" is just Sarah checking her phone during dinner,
that's your answer. Then double-check the legal angle—many "requirements" against
managed services vanish once you read the contract clauses closely.
Speaker 1: Treat architecture choices as living documents—review them at every
funding milestone.
Speaker 2: Build total cost of ownership models that include people, tooling, support
plans and the opportunity cost of moving slower.
Speaker 1: And sketch migration runbooks now. When the day comes to leave
serverless or exit a co-lo, you want a rehearsed plan, not a scramble.
Speaker 1: When teams feel stuck, a simple decision tree clarifies the next
move—speed, headcount and compliance narrow the field quickly.
Speaker 2: If you need a prototype in minutes, stay serverless. Fewer than three
engineers? Managed services keep you shipping without drowning in maintenance.
Speaker 1: And if regulators or customers insist on strict controls, you sketch a hybrid
or colocation footprint early so the surprise audits don't derail launch day.
Speaker 1: Self-managing hardware sounds cheaper, but the spreadsheet only works if
utilisation stays high and change cadence slows down.
Speaker 2: You now own spares, remote-hands visits, compliance paperwork and the
upgrade roadmap—none of that shows up on the first invoice.
Speaker 1: Make the shared-responsibility matrix explicit so the team knows who
patches, who backs up and who gets paged when the power strip fails.
Speaker 1: Risk management changes with each model—serverless still needs exports,
managed services need cross-region replicas, and racks need off-site backups.
Speaker 2: Vendor exit plans can't just be "download the data." Capture infrastructure
as code, schema migrations and performance benchmarks so switching is rehearsed.
Speaker 1: And keep a shared-responsibility matrix handy; knowing whether the
provider or your team handles identity, patching and incident response stops
finger-pointing when things break.
Speaker 1: The repeat offenders? Shipping a bespoke Kubernetes stack before you
have paying customers.
Speaker 2: Or ignoring data transfer fees—egress between regions can erase any
savings you thought you negotiated.
Speaker 1: And never assume "the cloud will just scale." Without budgets and
guardrails, you wake up to runaway spend and throttled APIs.
Speaker 1: Take Company X—they launched with three engineers on serverless
functions and rode that model to a million users.
Speaker 2: As workloads stabilised, they shifted core APIs to managed Kubernetes, then
added two colocated edge sites at ten million users to meet latency SLAs.
Speaker 1: Four years later, headcount hit fifteen, credits were gone, and they
negotiated enterprise contracts—because operating models evolve with scale.
Speaker 1: Wrap it up with homework—run the cloud pricing calculators with your real
numbers and growth bets.
Speaker 2: Set billing alerts now, not after finance sees a five-figure surprise, and
document the architecture assumptions you’re making today.
Speaker 1: Pair that with a RACI chart and exit criteria so when the next funding round
lands, you already know how to evolve the stack.
# Narrative Outline — Cloud vs On-Premise Decisions
## Tasks
- [x] Compare the trade-offs between serverless options, managed services and
self-managed infrastructure.
- [x] Highlight how AWS, Azure and GCP startup credits influence the decision path.
- [x] Frame questions founders should ask before committing to containers or keeping
everything in the cloud.
## Notes
- Evaluate free tiers across major cloud providers and when to adopt containers versus
staying serverless.
- Emphasise funding milestone checkpoints so teams revisit total cost of ownership and
operational readiness.
Day Zero Assessment Checklist
Speaker 1: [energetic] Before the first hire signs their offer letter, founders are already
juggling payroll, domains and customer trials.
Speaker 2: Right, and every shortcut we take with accounts or laptops in those first 48
hours becomes technical debt that haunts us like a badly written contract with your
co-founder's cousin.
Speaker 1: That is why we open with a day-zero checklist—it freezes the chaos long
enough to get intentional about who can touch what.
Speaker 2: And once it exists, you can run the same play every time a new teammate
or contractor joins instead of improvising access in Slack DMs.
Speaker 1: [practical] When you run the workshop, block 90 minutes and invite the
people who actually flip the switches—founders, ops, any MSP partner.
Speaker 2: I like to start by drawing the current system map on a whiteboard. Seeing
payroll tied to the bank, CRM feeding support, it grounds the conversation.
Speaker 1: Then nominate a scribe. Someone updates the checklist in real time so “we
should enable MFA” instantly becomes an owner plus due date.
Speaker 2: And before you move on, pause to log blockers—missing licenses, unclear
vendor contacts—so they don't end up in the startup graveyard of “we really should get
around to that someday.”
Speaker 1: [guiding] The checklist itself is four blocks: identity, endpoints, backups and
security governance.
Speaker 2: Give each line item a simple green, amber, red score. It keeps the
conversation focused on risk instead of blame.
Speaker 1: And remember to jot the system of record beside each control—Google
Workspace, Okta, a password manager—so you know where truth lives.
Speaker 2: That clarity also helps when you hand the assessment to a fractional CTO or
MSP; they can instantly see the hotspots.
Speaker 1: [focused] Identity is first because every other control depends on who can
log in where.
Speaker 2: Map each tool back to your source of truth—HR roster, Google,
Microsoft—and note whether MFA is enforced or still optional.
Speaker 1: Document the joiner, mover, leaver steps including who removes access at
5pm when someone resigns abruptly.
Speaker 2: And wherever you see shared logins or personal emails on vendor accounts,
highlight them for legal to renegotiate before renewal.
Speaker 1: [methodical] Endpoints are next. Start with a live asset list—owner, device
type, OS version, last patch date.
Speaker 2: It can be a spreadsheet to begin with, just make sure someone owns
keeping it current.
Speaker 1: Record your baseline build: encryption on, screen lock, approved software.
Consistency stops shadow IT before it spreads.
Speaker 2: And check you can remote wipe or at least lock a laptop. Founders travel,
gear gets left in rideshares, and suddenly your company's most sensitive data is racing
through downtown in someone else's Tesla.
Speaker 1: [analytical] For backups, identify the data that would hurt to lose—source
code, CRM, finance, product telemetry.
Speaker 2: Ask two questions: is there an automated backup, and when did we last test
restoring it?
Speaker 1: Capture how long the restore took and any surprises. That anecdote
becomes gold when auditors or investors ask about resilience.
Speaker 2: Also plan manual fallbacks—exporting CSVs, printing key docs—so the team
can keep shipping even while a vendor is down.
Speaker 1: [cautious] The security and monitoring section ties everything together.
Speaker 2: Review password policies, make sure default admin accounts are renamed,
and log authentication events somewhere you can actually search.
Speaker 1: Draft an incident contact tree now—who talks to investors, customers,
regulators—so you are not scrambling mid-crisis.
Speaker 2: And decide on vulnerability scanning cadence plus patch windows;
expectations set early are easier to enforce later.
Speaker 1: [outcome-focused] By the end of the workshop you should have tangible
outputs, not just a lively chat.
Speaker 2: That means a scored checklist, a 30/60/90 plan, refreshed runbooks and a
folder of evidence screenshots and policies.
Speaker 1: Book the follow-up review before everyone leaves the room—ideally before
the next hire or investor update.
Speaker 2: Treat it like any other deliverable: assign owners, due dates, and drop the
tasks into your project tracker right away.
Speaker 1: [career-minded] These assessments are often championed by fractional
CTOs, security-savvy ops managers or MSP onboarding leads.
Speaker 2: It is a fantastic shadowing opportunity for junior analysts—they learn
facilitation, stakeholder translation and control baselining.
Speaker 1: The real skill is empathy: explaining why MFA matters without sounding like
the “no” police.
Speaker 2: Nail that and you build the muscle to grow into head of IT, risk lead or
customer trust advocate roles as the company scales.
Speaker 1: [encouraging] Keep the checklist alive; review it after every hire, vendor
change or funding milestone.
Speaker 2: When investors or auditors call, you already have evidence folders and
owners lined up—it shifts the tone from defensive to confident.
Speaker 1: More importantly, the team knows what “secure enough” looks like today
and how it will mature tomorrow.
Speaker 2: That shared playbook turns day-zero chaos into a calm, repeatable ritual
that protects both momentum and trust.
# Narrative Outline — Day-Zero Startup IT Assessment
## Tasks
- [x] Design the interactive checklist covering identity, endpoints, backups and security
toggles.
- [x] Explain how to facilitate the checklist as a live workshop activity.
- [x] Clarify outputs participants should walk away with after completing the
assessment.
## Notes
- Draft the identity, endpoint, backup and security checklist used on day zero.
Day Zero Core Services
Speaker 1: Day-zero sounds dramatic, but it's literally the first five business days.
Speaker 2: Exactly—incorporation, domains, devices and security all race to go live
together.
Speaker 1: Miss a step and you're chasing paperwork while customers wait.
Speaker 2: So we map the whole week before the first hire even signs their contract.
Speaker 1: What's actually included in this "day-zero" checklist?
Speaker 2: Anything that makes the company real—legal filings, domains, baseline
tooling and who owns each task.
Speaker 1: So it's not just IT running off to configure email.
Speaker 2: Right, it's a cross-functional sprint with evidence you can show an MSP,
investor or auditor.
Speaker 1: We start with the boring stuff: entity registration and bank accounts.
Speaker 2: Boring until a contractor asks for payment and you realise payroll IDs aren't
ready.
Speaker 2: Or until a contractor sends an invoice and you discover "Awesome Startup
LLC" was never actually registered.
Speaker 1: Nothing kills the entrepreneur vibe faster than admitting you're technically a
sole proprietorship.
Speaker 1: Or a founder leaves and there was never a signed agreement.
Speaker 2: That's why day-zero includes a data room folder for all those artefacts.
Speaker 1: Domains feel simple—just buy the .com and you're done, right?
Speaker 2: Until someone forgets the .co or country code and a squatter grabs it.
Speaker 1: Or when the CEO's ex-partner controls the domain and decides to get
creative during the breakup.
Speaker 2: That's why we register defensives—and use business email, not the
founder's hotmail-from-college account.
Speaker 1: Or the registrar is tied to a personal Gmail account you can't access during
travel.
Speaker 2: Shared ops email, templated DNS records and uptime monitoring keep
launches from face-planting.
Speaker 1: Choosing Google Workspace versus Microsoft 365 still sparks debates.
Speaker 2: The real question is which ecosystem your customers expect and what
integrates with your stack.
Speaker 1: Either way, MFA on admin roles and shared mailboxes can't wait a month.
Speaker 2: And even if HR is a spreadsheet, sync it so joiners and leavers stay in
lockstep.
Speaker 1: Where do we keep the policies and meeting notes so they don't vanish in
chat history?
Speaker 2: Spin up a knowledge base on day one, even if it's a single-page Notion
workspace.
Speaker 1: And pre-build channels for incidents, board updates and customer
escalations.
Speaker 2: Templates save teams from reinventing emails at 2 a.m. when something
breaks.
Speaker 1: Hardware always turns up late unless you plan buffers.
Speaker 2: Exactly—keep a few imaged laptops ready with asset tags and shipping
labels.
Speaker 1: And there's always one founder who insists on a $4,000 gaming laptop "for
better performance."
Speaker 2: Which promptly gets coffee spilled on it during the first investor meeting.
Speaker 1: And don't forget travel kits for sales or fundraising trips.
Speaker 2: Record serials and warranties so replacements aren't a scavenger hunt.
Speaker 1: Security feels like overkill before the first customer signs.
Speaker 2: Yet that's when attackers love to strike—defaults are still wide open.
Speaker 1: So we turn on password managers, logging and break-glass accounts
immediately.
Speaker 2: And make sure founders know who to call—lawyers, insurers, incident
responders—if something goes sideways.
Speaker 1: Remind me about Sarah's DNS incident—you keep telling teams that story.
Speaker 2: She registered the domain with her personal email, deleted a wildcard
record at 1 a.m. and the demo site vanished for six hours.
Speaker 1: Investors called before breakfast and the sales team had to reschedule
every meeting.
Speaker 2: Now she keeps registrar access in a shared vault with change windows,
even with ten employees.
Speaker 1: How do we keep momentum once the checklist starts?
Speaker 2: Daily stand-ups, a Kanban board and a link to evidence for every completed
task.
Speaker 1: Plus async walkthrough videos so the next hire isn't blocked waiting for a
founder.
Speaker 2: And note which lawyers, accountants or MSPs you escalate to if things stall.
Speaker 1: So the goal is confidence that core services survive founder vacations and
audits.
Speaker 2: Exactly—treat day-zero as a living runbook, not a one-off launch party.
Speaker 1: When everything's documented, due diligence calls become show-and-tell.
Speaker 2: And the team can focus on customers instead of chasing missing DNS
logins.
# Narrative Outline — Day-Zero Core Services Setup
## Tasks
- [x] Map the first-week tasks for incorporating the company and provisioning core
services.
- [x] Explain choices for domain registration, productivity suites and lightweight device
procurement.
- [x] Weave in Sarah's "CEO learns DNS the hard way" cautionary tale as a teaching
beat.
## Notes
- Outline company incorporation steps, domain registration, productivity suite choices
and device procurement basics, including Sarah's DNS cautionary tale.
Fractional Cto And Msps
Speaker 1: Lean teams eventually hit a ceiling—product ambition outpaces leadership
bandwidth.
Speaker 2: That's when fractional CTOs and MSP partners start appearing in board
meeting minutes.
Speaker 1: The trick is to use them to accelerate maturity, not to abdicate the hard
decisions.
Speaker 2: So today we unpack when to bring each partner in and the questions that
keep expectations sane.
Speaker 1: Founders usually wait too long to admit they need senior guidance.
Speaker 2: Right—fractional leaders exist because hiring a permanent CTO takes
months and equity you can't spare.
Speaker 1: Virtual CIOs and MSPs handle different pain: governance, policy, 24/7
operations.
Speaker 2: Most engagements land in the 6 to 18 month window—long enough to
stabilise, short enough to keep urgency high.
Speaker 1: When cash is tight, trade 0.5 to 1 percent equity for part-time leadership
instead of a $150k salary you can't cover yet.
Speaker 2: Expect blended billing—retainers, day rates and per-incident fees—so model
the spend before you commit.
Speaker 1: Let's sort out who to call based on the mess in front of you.
Speaker 2: Product roadmap chaos? A fractional CTO sets architecture guardrails and
mentors engineering leads.
Speaker 1: Board grilling you on IT risk? A virtual CIO can own policy cadence while the
MSP implements the controls.
Speaker 2: And if pager duty is burning everyone out, the MSP has to anchor the help
desk and incident response.
Speaker 1: Engagement shape matters just as much as who you hire.
Speaker 2: An embedded fractional leader joins exec meetings weekly and steers hiring
and architecture.
Speaker 1: Some founders only need a six-week strategist to map the roadmap and
hand off to their own team.
Speaker 2: Co-managed MSPs keep product decisions in-house, but a full outsource
risks skills atrophying if you don't stay engaged.
Speaker 1: Vet a fractional CTO like you would a permanent exec.
Speaker 2: Ask which stages they've navigated—seed, Series B, messy
turnarounds—and what outcomes they achieved.
Speaker 1: Availability matters; if they juggle five clients, who shows up when your
production outage hits?
Speaker 2: Request artifacts—architecture memos, hiring scorecards—and learn
whether they coach, architect or swoop in as a fixer.
Speaker 1: MSP due diligence can't stop at a glossy pitch deck.
Speaker 2: Drill into incident response—who answers at 2 a.m. and what escalation
path they follow.
Speaker 1: Check their security posture and whether they'll integrate with your
ticketing and SSO instead of adding silos.
Speaker 2: And nail down the commercial model—after-hours rates, pass-through costs
and the fine print on exit clauses.
Speaker 1: Vendors love promising "unlimited" everything.
Speaker 2: My favourite line is "we onboard in a week"—sure, if you don't mind
copy-pasting scripts yourself.
Speaker 1: Use humour to keep it human, but make them show the runbook, the ticket
queue stats and who actually did the work.
Speaker 2: When they boast "our AI monitors everything", I ask to see the alerts that
drag them out of bed at 3 a.m.
Speaker 1: And "seamless integration" translates to "tell me how many API calls your
tooling will hammer our systems with".
Speaker 2: If they can't laugh and still produce evidence, that's a red flag before you
even sign.
Speaker 1: References tell you how providers behave when things get messy.
Speaker 2: Call past clients and ask how knowledge transfer went when the
engagement ended.
Speaker 1: Run a tabletop exercise before you sign—it reveals decision-making speed
and tooling depth.
Speaker 2: Don't forget subcontractors and insurance requirements; your customer
contracts probably demand both.
Speaker 1: Once the contract is signed, governance keeps everyone aligned.
Speaker 2: Start with a RACI—who owns roadmap, change approvals, incident
command and vendor spend.
Speaker 1: Run quarterly reviews with shared dashboards so surprises surface early.
Speaker 2: And agree on the exit plan now: documentation handover, credential
rotation and how long they'll stay during transition.
Speaker 1: Bottom line—fractional leaders and MSPs buy you time, not absolution.
Speaker 2: Use sharp evaluation questions and a bit of humour to expose gaps before
they turn into incidents.
Speaker 1: Then govern the partnership like any critical system with clear roles and exit
plans.
Speaker 2: For homework, draft five evaluation questions for your stage and swap them
with a peer for feedback.
# Narrative Outline — Working with Fractional CTOs and MSPs
## Tasks
- [x] Clarify when to engage fractional CTOs, virtual CIOs or MSP partners.
- [x] Capture the vendor humour about promises versus delivery to keep tone lively.
- [x] List questions founders should ask before signing support agreements.
## Notes
- Explain partnership models with fractional leaders and MSPs, including evaluation
questions.
Guest Speaker Ideas
# Guest Speaker Ideas — Narrative
Welcoming guest voices into the start-up IT module keeps the material grounded in
reality. The aim of this segment is to highlight three complementary perspectives that
expose learners to leadership, operational delivery and investor expectations. By
curating diverse experiences we show founders and early operators what "good" and
"risky" look like beyond theory.
## Why bring guest voices?
Open with the rationale: founders have endless frameworks but rarely hear candid
accounts of what actually happened during a crunch. Emphasise that each speaker
translates a different pressure point—technical firefighting, service delivery promises
and the scrutiny of outside capital. Call out that the goal is not inspirational talks; it is to
interrogate decisions and trade-offs.
## Fractional CTO perspective
Position the fractional CTO as the voice of experience when the wheels wobble. Have
them walk through their first 90-day plan: stabilise the architecture, triage tech debt,
prioritise hires and embed lightweight governance. Ask for stories contrasting a
pre-seed engagement—where they're duct-taping shipping velocity—with a Series B
client that needs compliance, forecasting and stakeholder management. Prompt them
to discuss pitfalls like unclear decision rights, unpaid scope creep and what happens
when teams assume an advisor is on-call 24/7. Close with a practical readiness
checklist founders can complete before reaching out to fractional leaders.
## Startup-focused MSP account manager
Introduce the MSP account manager as the operator who turns contracts into
day-to-day coverage. Encourage them to deconstruct a typical co-managed support
relationship: who fields which tickets, how they integrate tooling, what on-call
escalation looks like in practice. Ask for anonymised SLA dashboards showing healthy
and unhealthy trends so learners can interpret their own metrics. Cover pricing
levers—per device, per user, compliance surcharges—and how those evolve with
headcount or regulatory scope. Include guidance on running quarterly business reviews
that focus on backlog burn-down and continuous improvement rather than endless
upsells.
## VC diligence or portfolio operations lead
Frame the investor representative as a reality check on what external stakeholders
scrutinise. Have them outline their diligence checklist: security controls, revenue
instrumentation, resilience plans, staffing and cultural signals. Request anonymised red
and green flag examples pulled from data-room reviews—missing access logs, surprise
shadow IT, or great runbooks that sped up approval. Explore how IT maturity shifts
valuation conversations, board confidence and follow-on funding decisions. Reinforce
that the best preparation is building diligence-ready documentation and repeating
tabletop drills long before a term sheet appears.
## Logistics and prep tips
Spell out the operating rhythm so organisers are not scrambling. Recommend sourcing
speakers 6–8 weeks in advance, confirming NDAs, slide-sharing permissions and
accessibility needs. Pair each guest with a learner moderator responsible for research,
intros and audience questions; schedule a 30-minute prep call to align on flow. Provide
context briefs that summarise audience maturity, session goals and no-go topics.
Finally, plan to capture the session for reuse—obtain consent, organise recording and
editing support, and publish assets to the cohort hub with clear access controls.
## Call to action
Close the segment by nudging learners to practice outreach. Ask them to draft an email
to their dream guest—highlighting the topic fit, proposed format, audience size and how
they will make the speaker's time worthwhile. Invite a few volunteers to read their
drafts and workshop improvements live. Reinforce that thoughtful preparation and a
clear value exchange dramatically increase the hit rate when approaching busy leaders.
# Narrative Outline — Guest Speaker Ideas
## Tasks
- [x] Suggest a fractional CTO, startup-focused MSP account manager and VC diligence
lead.
- [x] Explain what each guest can contribute to learner outcomes.
- [x] Capture logistics for sourcing and prepping each speaker.
## Notes
- List potential guest experts and the perspectives they bring to the session.
Investor Due Diligence Prep
Speaker 1: [confident] Sarah's seed deck promised investors she could scale without
burning the place down—or turning the office into a literal or metaphorical dumpster
fire; now Series A questions are landing in her inbox daily.
Speaker 2: The slides we’re about to walk through are the playbook for proving that
promise isn’t just marketing glitter.
Speaker 1: Think of due diligence prep like running production change
management—clear owners, change logs and rollback plans.
Speaker 2: And just like change management, the calm comes from having evidence
ready before anything breaks in front of the board.
Speaker 1: [analytical] Series A partners now assume you've got discipline around
finance, security and customer retention.
Speaker 2: When they ask, "Show me your churn cohorts and your incident history,"
they're testing whether growth has guardrails.
Speaker 1: That pivot from pipeline to pen tests is their way of confirming discipline, so
the fastest way to erode confidence is to stall or improvise—every "let me get back to
you" adds friction to the deal.
Speaker 2: That’s why we start aligning evidence months before the outreach email
ever hits an investor’s inbox.
Speaker 1: [structured] We break diligence into three streams so nothing falls between
departments.
Speaker 2: Finance owns cash, contracts and SOC 2 timelines; security tracks access
controls and incidents; product captures roadmap and customer promises.
Speaker 1: A program manager or chief of staff keeps everyone aligned, running the
same cadence as sprint reviews—finance demos burn forecasts, security closes the "12
admin accounts" story, product shows roadmap deltas.
Speaker 2: Weekly stand-ups and a single tracker give investors confidence that the
team can execute across silos.
Speaker 1: [practical] Treat the data room like a product release—versioned,
documented and curated, with a changelog that shows new evidence landing every
week.
Speaker 2: Every file needs a cover note explaining what it is, why it matters and the
last review date, plus a contact person if investors want a deeper dive.
Speaker 1: Sarah colour-codes action items with due dates so investors see momentum
instead of a pile of gaps, and she tags blockers that need board attention.
Speaker 2: Sensitive exports stay in watermark-enabled folders with access logs; no
more "here's a spreadsheet" emails floating around, and expirations auto-trigger
reminders to revoke access.
Speaker 1: [alert] Security questionnaires look intimidating, but most questions repeat:
MFA, pen tests, backups, privacy.
Speaker 2: We front-load our red flags—shared admin accounts, missing asset
inventories—so investors see honesty, not surprise.
Speaker 1: Each gap gets a mitigation plan with owner, budget and timeline; for
example, "12 privileged accounts without MFA, YubiKey rollout funded at $15k and
complete by June 30." No vague "we're working on it" responses.
Speaker 2: A plain-language FAQ helps translate acronyms into outcomes for investors
and board members who aren’t security natives.
Speaker 1: [governed] Investors want to know who actually signs off on risk.
Speaker 2: We map every policy to a board sponsor or advisor—security charter to the
risk chair, finance controls to the audit lead.
Speaker 1: Decision logs show when exceptions were approved and by whom; it proves
governance is active, not theoretical, and highlights when legal or product weighed in.
Speaker 2: A shared calendar connecting audits, board reviews and certification
renewals keeps everyone in rhythm, with reminders like "Q2 risk committee + SOC 2
dry run" baked in.
Speaker 1: When the partner asks "Who closes the loop?" we point to the governance
RACI and invite them to our next tabletop recap.
Speaker 2: That transparency signals maturity—it feels like they're joining an existing
cadence instead of inventing one mid diligence.
Speaker 1: [data-driven] Dashboards alone won't close a round, but they anchor the
story in facts.
Speaker 2: Quarterly posture reports, uptime achievements and MTTR trends show
resilience in motion—"99.6% SLA hit, 12-minute MTTR" reads better than buzzwords.
Speaker 1: Pair the charts with narratives—"here’s the remediation we shipped after
that pen test"—so investors hear accountability and progress.
Speaker 2: We also surface how the risk register feeds Jira or Notion; governance
without execution is just wallpaper, and burndown charts prove tasks actually close.
Speaker 1: [coaching] Before the real investors arrive, we run a mock session with our
advisors playing the tough crowd.
Speaker 2: Each exec practices a two-sentence answer with a pointer to deeper
artefacts—no wandering monologues.
Speaker 1: We record the rehearsal, capture follow-up tasks and assign owners in the
tracker within the hour.
Speaker 2: That loop builds muscle memory so the actual diligence call feels like a
rerun, not improv night.
Speaker 1: [career-minded] Startups lean on program managers or chiefs of staff to
keep diligence humming.
Speaker 2: They partner with security or compliance leads who can translate
questionnaires into sprint-sized work.
Speaker 1: Finance and RevOps double-check the numbers and customer obligations so
nothing surprises the board.
Speaker 2: People who thrive here love diplomacy and structured storytelling—the
same skills that lead to VP Ops or trust leadership roles later.
Speaker 1: [wrap-up] The big lesson—start six months early and treat diligence like an
ongoing product, not a last-minute fire drill.
Speaker 2: When policies, metrics and board oversight line up, investors feel like
they're joining a machine that already runs.
Speaker 1: Red flags are inevitable, but owning them with a remediation plan shows
maturity, not weakness.
Speaker 2: And that transparency is exactly what keeps term sheets moving instead of
gathering dust in legal review.
# Narrative Outline — Preparing for Investor Due Diligence
## Tasks
- [x] Walk through sample security questionnaires and common red flags.
- [x] Connect preparedness to maintaining investor confidence.
- [x] Provide guidance on mapping policies to board expectations.
## Notes
- Describe diligence artifacts, common red flags and policy-to-board mapping tips.
Legal Compliance Reality Check
Speaker 1: We keep saying "we'll sort compliance after launch" but the enterprise pilot
is already asking for controls.
Speaker 2: Exactly why this session exists—let's map what "good enough" looks like so
we stop sprinting blind.
Speaker 1: SOC 2 feels mythical—people say it takes years and a room full of
consultants.
Speaker 2: Type I can land in a quarter if we assign an owner, reuse templates and
rehearse evidence pulls monthly.
Speaker 1: And Type II?
Speaker 2: Plan on nine months because auditors watch controls run; automation for
access reviews and logging keeps it sane.
Speaker 1: We're pulling in GPL, Apache and MIT libraries without thinking—what's the
real risk?
Speaker 2: Licences travel with your code; at minimum we owe attribution, and GPL
triggers source disclosures if our product distributes binaries.
Speaker 1: So we need a log of what we're using?
Speaker 2: Yes, a lightweight SBOM and approval step keep surprises out of vendor
questionnaires and customer audits.
Speaker 1: Our product team wants to ship a new analytics feature tomorrow—privacy
review feels like a blocker.
Speaker 2: Run the 15-minute DPIA template, strip optional personal fields and
document consent flows now; it's faster than rewriting code post-incident.
Speaker 1: Do we loop legal in on every tweak?
Speaker 2: Bring them in for cross-border data moves or sensitive categories, but
empower squads with reusable checklists for the routine cases.
Speaker 1: Who actually owns this when we're only twenty people?
Speaker 2: A fractional CISO or ops lead can captain it, with a privacy counsel on
retainer and an engineer automating the evidence pulls.
Speaker 1: What's the growth path for someone who loves this work?
Speaker 2: Start as compliance coordinator, step into trust and safety leadership, and
grow toward head of risk once the company scales.
# Narrative Outline — Legal and Compliance Reality Check
## Tasks
- [ ] Demystify SOC 2 and ISO 27001 timelines for lean teams.
- [ ] Address open source licence obligations for GPL, Apache and MIT components.
- [ ] Reinforce the "data privacy by design when you're moving fast" message with
examples.
## Notes
- Outline compliance milestones, open source obligations and privacy-by-design
guidance.
Lightweight Saas Selection
Speaker 1: When you're a 15-person team trying to close your Series A, speed is the
currency you trade in. Lightweight SaaS lets
you stand up the tooling you need in a single afternoon instead of waiting for a
six-week implementation.
Speaker 2: Exactly. And those usage-based tiers stretch the cash you have—why
commit to 500 seats of an enterprise suite when
you only have 40 people today? That's a lot of empty virtual chairs! You can redirect
that spend to hiring or customer acquisition.
Speaker 1: The admin experience matters too. Founders and ops leads can tweak
settings without a full-time systems engineer.
Speaker 2: Plus, many of these vendors build for startups. You get templates,
community playbooks, even credits programs that
keep you moving without red tape.
Speaker 1: Of course, going lightweight isn't free of trade-offs. Integrations are usually
stitched together with Zapier or
webhooks that break when APIs change.
Speaker 2: And the compliance story can be thin. Some vendors still only have a SOC 2
Type I report or keep data in a single
region, which rattles enterprise customers.
Speaker 1: Scalability also bites faster than you expect—API rate limits, seat caps,
throttled exports.
Speaker 2: Governance tends to be "trust your teammates" rather than granular roles.
Boards and auditors eventually demand more
control than these entry tiers offer.
Speaker 1: Let's map the collaboration layer. Slack Pro is usually the first stop because
it unlocks custom emoji and quick
integrations without heavy governance.
Speaker 2: But unless you budget for the business tier, message history disappears
after 90 days, and exporting data for
litigation is clunky. We watched a fintech lose a compliance dispute because the Slack
export stopped short of the disputed conversation.
Speaker 2: Discord has similar energy—great engagement, thin retention.
Speaker 1: Zoom or Google Meet keep live collaboration humming. Just remember,
running compliant webinars or recording every call
adds administrative load.
Speaker 2: For knowledge, Notion or Coda do double duty as wiki and project hub. The
flexibility is gold, but you need page naming
and permission rituals so nothing critical vanishes into a private workspace.
Speaker 1: For customer tickets, Help Scout and Freshdesk Growth hit the sweet
spot—mailbox feel, shared inboxes and basic
automation.
Speaker 2: They start to creak when you need change calendars or formal incident
timelines. That's where ITSM-heavy tools earn
their price tag.
Speaker 1: Internal request queues often live in Zendesk Team or Jira Service
Management Standard. They capture intake nicely but
don't track assets or approvals with enterprise rigor.
Speaker 2: Don't forget status comms. Tools like Statuspage Starter or Instatus are
budget friendly, yet stakeholder targeting and
single sign-on frequently sit behind the higher tiers.
Speaker 1: On the revenue side, HubSpot Starter and Pipedrive Advanced keep pipeline
hygiene simple—drag-and-drop stages,
workflow snippets, basic dashboards.
Speaker 2: Their limits show up when legal asks for data residency guarantees or when
RevOps needs sandbox environments to test
changes.
Speaker 1: Outreach blends nicely with Apollo.io or MailerLite for outbound. Apollo.io's
core plan gives you 10,000 email credits while MailerLite's $19 plan offers unlimited
sends, but you must
police opt-outs manually to stay compliant.
Speaker 2: And for customer success, tools like Vitally or Customer.io bring product
signals together. Just budget time to wire
APIs into finance and analytics so the health scores are trustworthy.
Speaker 1: Finance stacks often start with Xero or QuickBooks Online. They are brilliant
for multi-currency invoicing, but global
consolidation or complex approvals still need bolt-ons.
Speaker 2: Billing runs through Stripe or Chargebee Essentials. Subscription dunning is
polished, yet revenue recognition and tax
calcs remain spreadsheet-driven until you level up. One founder spent quarter-end
untangling ASC 606 deferrals across twelve spreadsheets just to satisfy auditors—and
the accountant swore the nightmares would stop only after they graduated to a
purpose-built rev-rec tool.
Speaker 1: Spend management is where Ramp and Airbase Essentials shine—instant
cards, reimbursement automation, real-time budgets.
Speaker 2: The caution is that procurement workflows and SOC reports mature later. If
auditors need evidence, you'll spend time
extracting CSVs rather than handing over dashboards.
Speaker 1: Let's rewind to the "Zoom-to-Teams" migration of 2023. The company
adopted Zoom early because it just worked, while
Slack carried the daily chatter.
Speaker 2: Fast forward to 180 staff and a new security-conscious customer base. They
rolled out Microsoft 365 for compliance,
which meant duplicate calendars and two separate chat ecosystems.
Speaker 1: Finance spotted duplicate spend. Meanwhile IT worried about eDiscovery
and identity fragmentation.
Speaker 2: A migration squad catalogued every recurring meeting, webinar and
recording, then mapped them into Teams. Training,
etiquette guides and office hours smoothed the change.
Speaker 1: Afterward they saw real savings and better governance, though they kept
Zoom for big external webinars until Teams
caught up—showing that hybrid models can be strategic, not a failure.
Speaker 1: How do you know it's time to level up? One clue is when legal hold or data
residency questions keep coming up and your
vendors shrug.
Speaker 2: Another is the onboarding backlog. If provisioning accounts across a dozen
admin consoles takes days, you're building
risk with every new hire.
Speaker 1: Finance feels it too—when reconciliation means exporting CSVs into
spreadsheets every Friday night, you need deeper
integrations.
Speaker 2: Customer requests for SOC 2 Type II or HIPAA attestations, plus board
pressure for unified dashboards, usually tip you
over the edge into enterprise territory.
Speaker 1: Before you chase the next tool, document the non-negotiables—SSO, audit
logs, retention, whatever protects your team.
Speaker 2: Then score vendors on how well they plug into identity, CRM and data
platforms. Integration debt is expensive later.
Speaker 1: Pilot with a single squad and capture the hidden costs: admin hours,
training, the shadow IT workarounds.
Speaker 2: Finish with a total-cost-of-ownership view. Upgrades, add-ons,
migrations—they all belong in the spreadsheet. Review
the stack quarterly so you can renegotiate or sunset tools before they become technical
debt.
# Narrative Outline — Selecting Lightweight SaaS Platforms
## Tasks
- [x] Map lightweight options for collaboration, ticketing, CRM and finance at Series A
scale.
- [x] Include the "Great Zoom-to-Teams migration of 2023" mini-case to spark
discussion.
- [x] Flag signals that it is time to graduate to enterprise platforms.
## Notes
- Cover SaaS selection trade-offs and the Zoom-to-Teams migration case study.
Mock Vendor Evaluation Exercise
# Slide 1 — Mock Vendor Evaluation Exercise
Speaker 1: Picture procurement as a dusty kettlebell. Everyone nods at it, no one lifts.
Tonight we do.
Speaker 2: But why mock evaluations instead of just diving into real ones?
Speaker 1: Because the last team that skipped rehearsal picked a charming helpdesk,
then mid-migration learned it synced five integrations. Fixing that cost double.
Speaker 2: So this is our flight simulator: real decks, fake money, permission to stall
safely.
Speaker 1: Exactly—structured reps, a dash of humour, time to flag hype before the
next “this will revolutionise your workflow” email.
# Slide 2 — Exercise objectives
Speaker 1: Our scoreboard tonight isn’t “pick Zendesk” or “pick Intercom.” It’s “can we
run evaluation without drama?”
Speaker 2: We test how well we surface hidden assumptions, negotiate respectfully,
and document decisions like adults.
Speaker 1: Exactly. When the Series A board call asks why you chose Vendor A over B,
you’ll have receipts instead of vibes.
Speaker 2: And we leave with artefacts—scorecards, negotiation scripts, reference-call
checklists—that seed the procurement playbook.
Speaker 1: Plus the muscle memory to brief execs in plain English instead of jargon
bingo. That confidence is the real win condition.
# Slide 3 — Scenario setup
Speaker 1: Context—our support queue has outgrown a scrappy inbox plug-in. We’re
weighing Zendesk versus Intercom for the next growth spurt.
Speaker 2: Leadership wants a recommendation in two weeks.
Speaker 1: Ouch, two weeks? That's startup speed for you! We ship releases while
running vendor due diligence.
Speaker 2: Budget caps at $120K, SOC 2 is non-negotiable, and migration must land
before the holiday spike. It’s like switching planes mid-flight.
Speaker 1: So we document the “why,” not just the “who.” If turbulence hits, the
logbook shows our trade-offs and the backup parachute plan.
# Slide 4 — Roles and personas
Speaker 1: The evaluation lead conducts the orchestra—sets tempo, invites dissent,
keeps the scorecard honest.
Speaker 2: Finance plays skeptic, probing cost, discount ladders, and what happens
when usage blows past the tier.
Speaker 1: Security and compliance are our “department of no, but.” They bring veto
power plus mitigations so the plane still flies.
Speaker 2: The support lead guards adoption, change management checklists, and
whether onboarding beats last quarter’s fiasco.
Speaker 1: The CEO observer is the storytelling boss. If they can retell your
recommendation without notes, you’ve cleared the level.
# Slide 5 — Preparation checklist
Speaker 1: Prep starts with two vendor dossiers—pricing pages, security briefs, a
HubSpot implementation guide if we’re stacking it against Salesforce Service Cloud.
Speaker 2: Everyone gets the same scorecard so debates hit weighting, not whether
“reporting” belongs at all.
Speaker 1: Discovery notes keep us anchored in customer pain instead of vendor bingo
squares. They’re the antidote to “trust me, it scales.”
Speaker 2: Pre-work matters: each persona brings deal-breaker questions and logs
assumptions in the shared doc.
Speaker 1: That discipline keeps the live session on decisions, not rummaging through
Slack for missing context.
# Slide 6 — Live role-play flow
Speaker 1: Phase one, kick-off—evaluation lead sets the clock, states decision criteria,
and assigns who plays the vendor rep.
Speaker 2: Phase two, breakout analysis—we pair up, annotate dossiers, and log gaps
in shared notes instead of sticky pads.
Speaker 1: Phase three, negotiation sprint—finance haggles on payment terms while
the “vendor” guards implementation scope. Fifteen minutes, zero table-flipping.
Speaker 2: Phase four, security challenge—compliance probes breach history, data
residency, and redlines they’d refuse.
Speaker 1: Phase five, executive pitch—we regroup, deliver a tight deck, and field
curveballs about migration risk and change management support.
# Slide 7 — Discussion prompts by phase
Speaker 1: Kick-off prompt: what assumptions are we making about migration effort or
weekend coverage?
Speaker 2: Follow-up: who owns reference calls and what answers would make us walk
away?
Speaker 1: Breakout prompt: how does each roadmap support the bets we just pitched
investors?
Speaker 2: Negotiation prompt: would we trade a 10% discount for guaranteed
onboarding hours or stronger exit clauses?
Speaker 1: Security prompt: show pen-test summaries, breach notices, and data
residency maps.
Speaker 2: Executive prompt: how will we track adoption in 30, 60, 90 days without
creative spreadsheet fiction?
# Slide 8 — Scorecard and documentation
Speaker 1: The scorecard anchors weighted dimensions—functionality, security, total
cost, implementation effort, vendor viability.
Speaker 2: No random numbers. Each score needs a quote, link, or screenshot so future
you can retrace the decision.
Speaker 1: Breadcrumbs help when a new CFO asks why HubSpot beat Salesforce or
why we skipped the flashy AI add-on.
Speaker 2: The decision matrix lives in a shared workspace with version history.
Governance isn’t glamorous, yet auditors adore it.
Speaker 1: Open risks get owners, mitigation dates, and escalation paths. No orphaned
yellow flags—documentation becomes insurance when memories fade.
# Slide 9 — Debrief structure
Speaker 1: Debrief starts with “what worked” so we reinforce behaviour to
repeat—transparent notes, quick risk spotting, vendors kept honest.
Speaker 2: Then “what puzzled us.” Perhaps Intercom’s security appendix contradicted
the sales pitch or our change management plan felt thin.
Speaker 1: Every insight lands in the shared doc—no hallway wisdom vanishing before
Monday.
Speaker 2: Action commitments need names and dates. Who’s refining the scorecard?
Who’s booking reference calls for the evaluation?
Speaker 1: Close with feelings check-ins by persona. Did finance feel heard? Did
support believe the adoption plan? Reflection locks in trust.
# Slide 10 — Success criteria and follow-through
Speaker 1: Success is a memo you’d hand the CEO without sweating—recommendation,
quantified impact, clear risks, and a backup plan.
Speaker 2: The executive observer should retell the story unaided. If they need us
nearby, we didn’t simplify enough.
Speaker 1: Templates, negotiation notes, and reference-call scripts land in the
procurement playbook within 24 hours.
Speaker 2: Then we book next drill or live evaluation. Procurement is the vegetables of
business—better when routine.
Speaker 1: Finally, assign owners for vendor relationship management: quarterly health
checks, roadmap reviews, and change management follow-ups so momentum sticks.
# Narrative Outline — Mock Vendor Evaluation Exercise
## Tasks
- [x] Set up the role-play using real SaaS pricing pages.
- [x] Include prompts for explaining backup costs to the CEO.
- [x] Define success criteria for the exercise debrief.
## Notes
- Outline the vendor evaluation role-play structure and discussion prompts.
- Narratives emphasise role immersion, documentation discipline, and executive-ready
storytelling.
Pre Seed Tool Stack
Speaker 1: [upbeat] Welcome to our pre-seed stack tour—eleven slides to prove that
discipline beats signing up for every shiny SaaS trial.
Speaker 2: Exactly. We are keeping the runway intact while still looking like grown-ups
to customers, investors and auditors-in-training.
Speaker 1: Think of this session as giving Sarah a starter pack she can actually afford to
run for six months.
Speaker 2: And it sets the tone for future upgrades—we are deliberate, not reactive.
Speaker 1: [curious] Before we jump into vendor logos, let's clarify why a curated stack
matters.
Speaker 2: Every new hire brings their "game-changing" productivity app—suddenly
you're managing more tools than team members.
Speaker 1: Worse, diligence calls expose the chaos when investors ask "who
administers access" and the answer is "we'll get back to you".
Speaker 2: A lean, intentional toolkit gives Sarah language for governance without
drowning in enterprise overhead.
Speaker 1: [pragmatic] Here are the guardrails—around two hundred dollars a month
for six to eight active seats.
Speaker 2: That number keeps payroll sane while covering email, chat, documentation
and security basics.
Speaker 1: Monthly billing matters; long contracts feel cheaper but they erode
optionality if the product pivots—or dies.
Speaker 2: And track the bots—automation accounts often quietly consume paid
licences like hungry ghosts in your billing system.
Speaker 1: [informative] Google Workspace Starter gives us admin controls, shared
drives and basic DLP for seventy-two dollars.
Speaker 2: Pair that with Slack Pro so conversations are searchable and partners can
join via shared channels without legal headaches.
Speaker 1: We hold off on enterprise SSO because no customer has demanded it
yet—that's the upgrade trigger.
Speaker 2: And if someone insists on Microsoft 365, document migration time, identity
mapping, data residency shifts and the training burden before agreeing—you might
discover it's a $10K decision disguised as a $20/month subscription.
Speaker 1: [thoughtful] Notion handles company wiki, retrospectives and investor
updates for thirty-two dollars—just remember it can become a black hole where
documentation goes to die without clear structure.
Speaker 2: Airtable fills the structured gap—a light CRM and operations tracker without
buying a full Salesforce instance.
Speaker 1: The discipline is resisting app sprawl; we build new workflows inside these
tools before swiping cards elsewhere.
Speaker 2: Also audit the editor list monthly—lots of contributors only need viewer
seats, and embed onboarding SOPs so new hires ramp fast.
Speaker 1: [serious] Security cannot wait until Series A, so 1Password anchors secrets
management for twenty-four dollars.
Speaker 2: We capture onboarding checklists inside the vault—who gets which shared
vault, when MFA is confirmed, what to rotate.
Speaker 1: Hardware keys and CASBs are overkill today; instead we enable
context-aware access inside Google Workspace.
Speaker 2: The win is standardising joiner, mover and leaver flows so offboarding is
muscle memory—otherwise that three-month contractor still has Drive access half a
year later.
Speaker 1: [balanced] Some add-ons are worth the spend, but only when the pain point
is measurable.
Speaker 2: Calendly saves hours once demos exceed ten a week—otherwise you've
spent money to schedule meetings you haven't had yet.
Speaker 1: Payroll platforms like Gusto or Rippling become necessary when contractor
invoices arrive monthly.
Speaker 2: And a support desk like Freshdesk only earns its keep when shared inbox
triage starts missing customer deadlines; double-check the API and SSO hooks first so
you don't rack up integration debt.
Speaker 1: [cautious] Upsell pressure is relentless, so we script polite "not yet"
responses.
Speaker 2: Slack's enterprise team will dangle grid analytics—Sarah waits until a signed
enterprise contract demands exports.
Speaker 1: Google will email about storage limits; that upgrade happens only when the
current quota truly blocks delivery.
Speaker 2: And any so-called founder discount tied to 24-month commitments gets
weighed against runway reduction and pivot risk—remember the Enterprise rep
boasting 99.99% uptime when your Pro plan already meets every SLA.
Speaker 1: [encouraging] Customisation is fine as long as the budget guardrail survives.
Speaker 2: If Sarah swaps Google for Microsoft 365 because the product uses Azure AD,
she documents the rationale and new admin tasks.
Speaker 1: Same story with replacing Airtable—maybe HubSpot Starter makes sense
once marketing automation matters.
Speaker 2: Every substitution goes into a single source of truth covering billing owners,
renewal dates, data export paths and how to unwind vendor lock-in.
Speaker 1: [interactive] Time to apply it: learners craft their own six-tool stack under
two hundred and fifty dollars.
Speaker 2: They justify each pick, list the upgrade trigger and nominate an owner for
governance.
Speaker 1: Sharing that "stay lean" checklist with peers invites constructive pushback
before real money gets spent.
Speaker 2: It's rehearsal for the boardroom question: "Why this tool, why now, and what
happens if it fails?"
Speaker 1: [confident] The takeaway is simple—startups win when every tool purchase
has a runway impact statement.
Speaker 2: Collaboration, knowledge, security and customer touchpoints are covered
without losing agility.
Speaker 1: Treat each new app as an experiment with success criteria and an exit plan.
Speaker 2: That mindset protects cash, keeps audits boring and leaves room to scale
when product-market fit finally lands.
Regional Compliance Considerations
Speaker 1: [upbeat] The moment you land customers outside your home city,
regulators start treating you like a global player.
Speaker 2: Exactly. Even a two-person fintech beta in Melbourne gets quizzed on GDPR,
SOCI and whatever acronym the prospect's legal team woke up thinking about.
Speaker 1: So this session is about building guardrails before the sales team promises
"enterprise-ready" compliance during the next demo.
Speaker 2: Think of it as future-proofing the trust you sell alongside the product.
Speaker 1: Let's anchor the big rocks—privacy, payments, data residency and any
sector-specific extras.
Speaker 2: Privacy is the loudest: consent, breach notifications, data subject rights.
GDPR, CPRA, LGPD—they all want receipts.
Speaker 1: Payments bring PCI DSS and strong customer authentication. Miss those and
Stripe pauses your account faster than you can say "chargeback".
Speaker 2: And data residency? Promising EU-only storage while quietly backing up to a
US S3 bucket is how trust evaporates.
Speaker 1: Different regions remix those obligations. The EU demands DPIAs and
updated Standard Contractual Clauses post-Schrems II.
Speaker 2: North America throws a state-by-state puzzle at you—California, Quebec,
New York cybersecurity regs. Plus the SEC now expects rapid incident disclosures.
Speaker 1: APAC has its own texture: Singapore's PDPA accountability principle, India's
new DPDP consent clauses, Japan's APPI transfer logs.
Speaker 2: And don't forget LATAM and the Gulf—Brazil's LGPD clock starts ticking the
moment you detect an incident, while Saudi's PDPL cares deeply about localisation.
Speaker 1: Compliance isn't only statutory; contracts sneak in heavyweight obligations
too.
Speaker 2: Procurement will ask for deletion within 24 hours, breach notifications inside
one business day and the right to audit your sub-processors.
Speaker 1: Payment gateways pile on quarterly scans or incident playbooks before you
get production credentials.
Speaker 2: Which means ops, engineering and customer success need a single map
translating contract promises into real workflows.
Speaker 1: Let's talk maturity curve. Early days look like personal Dropbox and a shared
LastPass vault.
Speaker 2: Then someone sells to a bank and suddenly you need a Record of
Processing Activities, access reviews and documented change control.
Speaker 1: By the time you reach mature stage, there's a privacy counsel, regional data
stewards and automated evidence gathering for audits.
Speaker 2: The key is to move deliberately, not wait for a due diligence fire drill to force
the transition.
Speaker 1: My favourite milestone is when the CEO finally retires their personal
Dropbox.
Speaker 2: The board meeting where you announce "invoices are no longer stored in
someone's Downloads folder" deserves a cake.
Speaker 1: That humour helps teams embrace policy—"our audit trail moved out of the
sharehouse" becomes shorthand for growth.
Speaker 2: Exactly. Celebrate the glow-up so compliance feels like progress, not
punishment.
Speaker 1: Practically, start with a risk register listing laws, customer commitments and
contract clauses.
Speaker 2: Tie each risk to a trigger—"Launch in Germany" equals DPIA, "Healthcare
pilot" equals HIPAA review, "Marketplace integration" equals PCI rescan.
Speaker 1: Assign owners early: legal on policy language, security on technical controls,
operations on evidence capture.
Speaker 2: And review the register quarterly so the roadmap stays aligned with pipeline
reality.
Speaker 1: Tooling helps when headcount is thin. A well-tagged Notion space can act as
your governance portal.
Speaker 2: Automate intake for data subject requests through your help desk, and use
cloud region controls to prove data residency without spreadsheets.
Speaker 1: Logging and key management double as audit evidence when customers
ask "who touched my data and where does it live?"
Speaker 2: Even lightweight automation makes the difference between scrambling and
calmly exporting proof.
Speaker 1: Finally, know when to call in experts—fractional privacy officers, local
counsel, MSP partners.
Speaker 2: They bring cultural context too. Translating consent language or adapting
incident comms for a new market builds trust faster.
Speaker 1: Join communities like IAPP or AISA so you're not reinventing the wheel.
Speaker 2: Bottom line: you don't need a 40-person compliance team, but you do need
intention. Let the Dropbox joke mark the moment governance finally caught up with
ambition.
# Narrative Outline — Regional Compliance Considerations
## Tasks
- [x] Highlight privacy, payment and data residency obligations when selling globally.
- [x] Contrast informal practices with the need for governance as the company matures.
- [x] Include humour about moving from personal Dropbox to enterprise retention
policies.
## Notes
- Summarise global compliance pressures and data governance expectations.
Remote First Reality Check
Speaker 1: "Remote-first" gets tossed around, but most teams still think HQ-first.
Speaker 2: Exactly—policies say "work from anywhere" while approvals still assume you
can walk to finance.
Speaker 1: Remote-first means devices, decisions and rituals travel as easily as the
people do.
Speaker 2: Which is why IT, ops and culture leads need the same playbook before the
next cohort lands.
Speaker 1: How many of you have felt that lurch when the "remote-friendly" promise
meets missing equipment on day one?
Speaker 2: Tonight we fix that gap—logistics, security and belonging in one loop.
Speaker 1: Let's map the first month so nothing falls between time zones.
Speaker 2: Pre-day zero we confirm paperwork, ship gear, load accounts and drop the
welcome checklist in their inbox.
Speaker 1: Week one stays async on purpose—People Ops hosts videos, buddies handle
the human check-ins.
Speaker 2: Week two we queue recorded shadowing; leads annotate playlists so new
folks binge the right calls.
Speaker 1: By week three the manager and mentor co-review their first real deliverable
using a shared rubric.
Speaker 2: Success looks like access ready on day one, first ship within 14 days and a
CSAT above 4.5—hold us to it.
Speaker 1: Most teams say they're remote-friendly until their star developer's laptop
dies in Mumbai at 3am.
Speaker 2: And suddenly "just bring it to IT" becomes a week-long international
shipping nightmare.
Speaker 1: We keep persona-based spares with zero-touch images, so Sarah in Berlin
had a twin MacBook within 48 hours.
Speaker 2: Depot partners plus customs-ready paperwork beat panic and prevent the
scenic tour of three warehouses.
Speaker 1: When BYOD is inevitable, we pair the stipend with MDM so that gaming rig
never touches prod without controls.
Speaker 2: Seriously, how many projects have you seen derailed by a customs delay or
a missing VPN token?
Speaker 1: Joiner-mover-leaver runbooks are where trust either lives or dies.
Speaker 2: Automation fires from HRIS updates so access bundles land without tickets.
Speaker 1: Maria's contract ended Friday; within minutes the bot revoked Figma, Slack
and VPN—no heroics required.
Speaker 2: The same playbook pushes MFA kits, password managers and VPN keys on
day one.
Speaker 1: We review those flows quarterly so they stay faster than "let me find the
spreadsheet" improvisation.
Speaker 2: Because if access takes hours, shadow IT takes minutes.
Speaker 1: Contractor programs crumble when identities stay tied to founder logins.
Speaker 2: Issue company-managed accounts, even if they're short-term, so auditing
isn't a scavenger hunt.
Speaker 1: When Maria finished her three-month design sprint, HR closed the ticket and
automation clipped every tool within minutes.
Speaker 2: And yes, if expense approvals take six weeks, expect a private Dropbox
empire to bloom overnight.
Speaker 1: Quarterly access reviews keep scope creep honest and surface contractors
who quietly became team members.
Speaker 2: We pair every exit with a gear return label so hardware doesn't retire in
someone's guest room.
Speaker 1: Time zones don't have to be chaos if choreography is deliberate.
Speaker 2: Coverage maps plus core hours make escalations clear before anything
breaks.
Speaker 1: The handover template saved us when London spotted a blocker at 6pm and
Sydney wouldn't wake for eight hours.
Speaker 2: We left annotated Looms, so Melbourne picked up without pinging anyone at
2am.
Speaker 1: We also killed the myth of the "quick sync"—turns out people prefer sleep to
sprint planning.
Speaker 2: So ask every team: which decisions truly require synchronous time, and who
pays the sleep tax when they do?
Speaker 1: Remote help desks work when support feels like a chat ping, not a ticket
abyss.
Speaker 2: Triage bots route laptop issues, while office hours catch the humans who'd
rather talk.
Speaker 1: We stock spare devices in regional lockers so replacements land within 48
hours.
Speaker 2: And every shipment includes customs paperwork pre-filled—future us loves
that version of us.
Speaker 1: Shipping SLAs and MTTR live on the same dashboard as CSAT so ops and
support stay aligned.
Speaker 2: Fix problems fast and people stop improvising with personal Dropbox links.
Speaker 1: Logistics done right is the runway for culture.
Speaker 2: When equipment arrives ready and access just works, people feel trusted
from the start.
Speaker 1: That trust buys time for buddies, rituals and storytelling to stick.
Speaker 2: We pair every new hire with a culture buddy outside their line so they hear
the unwritten norms.
Speaker 1: Regional micro-retreats turn Slack handles into people without demanding
relocations.
Speaker 2: Async updates rotate hosts so everyone practices belonging, not just the
loudest timezone.
Speaker 1: If we can't measure the experience, we can't improve it.
Speaker 2: Hardware lead time, access MTTR, onboarding CSAT—they're our new
uptime metrics.
Speaker 1: Track customs delays next to support queues so we know when logistics,
not tech, is the blocker.
Speaker 2: And audit SOP coverage; gaps there explain why shadow IT blooms in the
first place.
Speaker 1: Leaders love dashboards—give them the remote equivalent of footfall and
badge swipes.
Speaker 2: Otherwise they default to "are people online" instead of "are systems
keeping promises".
Speaker 1: Let's land this with actions you can execute Monday morning.
Speaker 2: Start by auditing onboarding artefacts—videos, SOPs, access flows—against
the last hire's pain points.
Speaker 1: Lock in logistics partners now so the next failed device gets replaced in
hours, not weeks.
Speaker 2: Wire offboarding triggers to payroll and SaaS so there are no lingering
zombie accounts.
Speaker 1: Revisit quiet hours, stipends and retreat budgets quarterly; remote teams
evolve fast.
Speaker 2: And after each cohort, ask "what made remote feel easy"—then scale that
habit intentionally.
# Narrative Outline — Remote-First Reality Check
## Tasks
- [x] Explain logistics for shipping devices and managing remote onboarding and
offboarding.
- [x] Discuss policies for contractor-heavy, globally distributed teams from day one.
- [x] Call out pitfalls when support is entirely virtual and time zones clash.
## Notes
- Cover remote onboarding, device logistics and managing a distributed contractor
workforce.
Remote Talent Logistics Scale
Speaker 1: Once you pass the first hundred remote hires, the "we'll figure it out" era
ends.
Speaker 2: Exactly. Logistics becomes a product—you ship experiences, not just
laptops.
Speaker 1: Our goal in this session is to replace heroics with systems that scale without
burning people out.
Speaker 2: Think of it as upgrading from a craft table to a production line while keeping
the same care for each new teammate.
Speaker 1: Remember when three people approved every laptop and the spreadsheet
lived on someone's desktop?
Speaker 2: That breaks the moment you scale to six countries and run parallel hiring
sprints.
Speaker 1: We need clear personas, automation triggers and regional partners ready
before the next wave hits.
Speaker 2: The promise is bold: day-two productivity without begging for favours across
time zones.
Speaker 1: Personas are our anchor—engineers, customer advocates, executives each
need a standard kit.
Speaker 2: Publishing SKUs, accessories and MDM policies keeps procurement and
finance aligned.
Speaker 1: It also means we can hold 5–10% buffer inventory per region without
guesswork.
Speaker 2: Quarterly vendor reviews let us refresh specs while keeping the automation
scripts intact.
Speaker 1: Shipping is only half the battle; we need visibility from purchase order to
first login.
Speaker 2: A shared dashboard shows customs holds, delivery confirmations and
first-day check-ins.
Speaker 1: When something breaks, regional depots with prepaid return labels make
swaps painless.
Speaker 2: And don't forget the back end—automated warranty claims and certified
e-waste partners close the loop.
Speaker 1: Hardware without access is just an expensive paperweight.
Speaker 2: HRIS triggers push identities through SCIM into Okta or Entra, bundling the
right apps per persona.
Speaker 1: For technical teams we rely on infrastructure-as-code to grant scoped
secrets and repos.
Speaker 2: Even service accounts get expiry dates—no more zombie credentials
haunting audits.
Speaker 1: Provisioning is great, but who checks access six months later?
Speaker 2: Quarterly attestations inside the IAM tool keep managers accountable with
usage data baked in.
Speaker 1: High-risk systems drop to 30-day reviews with dual approvals so nothing
slips.
Speaker 2: Every remediation produces an audit-ready trail—tickets, timestamps and
revoked roles.
Speaker 1: Logistics isn't only devices—payroll and benefits shape trust just as much.
Speaker 2: Integrating Deel, Remote or Papaya with the HRIS means contracts, taxes
and payslips land on time.
Speaker 1: Benefits aggregators help localise wellness stipends and statutory coverage
without manual spreadsheets.
Speaker 2: Syncing holidays and time-off feeds prevents payroll from deducting leave
twice for the same festival.
Speaker 1: Technology only works if culture keeps pace with geography.
Speaker 2: Regional ambassadors run welcome rituals, wellness budgets and office
hours in native time zones.
Speaker 1: Leadership rotations and quarterly meetups signal visibility without forcing
relocation.
Speaker 2: Written playbooks on etiquette and holiday swaps stop HQ norms from
steamrolling local practices.
Speaker 1: What do we watch to know the machine is working?
Speaker 2: Start with time-to-productive—device ready and core access within 48
hours.
Speaker 1: Layer access drift metrics and payroll accuracy so finance, security and
people ops share one scorecard.
Speaker 2: Pair it with employee pulse surveys; logistics CSAT and attrition by region
show where the experience cracks.
Speaker 1: Let's land on a 90-day plan so this doesn't stay theoretical.
Speaker 2: Month one, lock persona catalogs and sign logistics SLAs with service level
targets.
Speaker 1: Month two, light up HRIS-to-IAM automation, then pilot payroll and benefits
integrations in two countries.
Speaker 2: Month three, launch the cultural ambassador network and bake surveys into
the operating rhythm.
# Narrative Outline — Remote Talent Logistics at Scale
## Tasks
- [x] Detail how to standardise equipment and automate access reviews as headcount
grows.
- [x] Mention integrations for global payroll and benefits providers.
- [x] Address cultural considerations when expanding remote-first operations.
## Notes
- Describe scaling remote logistics, from hardware standards to automated access
reviews.
Scaling Support Processes
Speaker 1: Remember when founders personally reset Wi-Fi routers? That was
charming at 10 people, but now it blocks product roadmaps.
Speaker 2: Exactly. We're here to show why scaling support is a strategic investment,
not just cleaning up after everyone else.
Speaker 1: We'll move from chaos to a predictable service desk that earns trust from
executives, auditors and customers alike.
Speaker 2: And we’ll do it without copying enterprise bureaucracy—this is about the
minimum viable maturity that still scales.
Speaker 1: First clue you’ve outgrown ad hoc support? Slack DMs turn into a roulette
wheel of "Did anyone pick this up?"
Speaker 2: My other favorite—new hires shadow for a week because there’s no
knowledge base, just tribal lore from the first sysadmin.
Speaker 1: Finance notices too. Without ticket data there’s no way to justify headcount
or tool spend.
Speaker 2: And compliance folks get nervous when you can’t produce incident logs
during a customer audit. That’s the burning platform for change.
Speaker 1: Meanwhile remote teammates wait overnight for laptop fixes because
coverage lives in one time zone.
Speaker 1: The temptation is to just buy a tool, but the first step is designing intake and
triage.
Speaker 2: Right—choose one doorway for tickets. Portal plus email alias, both feeding
the same queue with required fields.
Speaker 1: Then define what "good" looks like: simple SLAs and an escalation ladder.
Even a Trello board can work if the process is crisp.
Speaker 2: Daily standups make invisible work visible, and a weekly retro keeps the
backlog honest. Tooling only amplifies that discipline.
Speaker 1: Knowledge bases fail when they become graveyards. We want a living
system tied to ticket closure.
Speaker 2: Exactly—agents draft the article while the fix is fresh, and SMEs review it
during their Friday hour of power.
Speaker 1: Short videos and annotated screenshots beat long prose for startup teams
moving fast.
Speaker 2: And don’t forget analytics. Track search terms with zero results, then
prioritize new content from that list.
Speaker 1: Once that foundation is in place, we can talk tooling choices that reinforce it
instead of creating another content graveyard.
Speaker 1: Let’s tackle the tooling debate. ServiceNow or Jira Service
Management—what’s the difference in practice?
Speaker 2: ServiceNow shines when you need rigid workflows, integrated CMDB and
audit-grade change control. But it demands budget and a specialist admin.
Speaker 1: Jira Service Management snaps into existing Atlassian workflows and ships
with great automation and developer visibility.
Speaker 2: The trade-off? You may need marketplace apps for CMDB depth and more
governance features. So we map regulatory needs, current stack, and admin skills
before deciding.
Speaker 1: Tool choice settled, the next lever is automation. Otherwise the team
becomes human routers.
Speaker 2: Start simple—Slack or Teams forms that capture device, urgency and
screenshots, then auto-tag the ticket.
Speaker 1: Sync asset data from MDM nightly so agents trust the CMDB when
troubleshooting.
Speaker 2: And hook the workflow engine to HR events so joiner, mover and leaver
tasks fire automatically. That’s hours back every week.
Speaker 1: Wrap those flows with security checks—privileged access reviews and
phishing simulations—so operations and security grow together.
Speaker 1: Processes mean nothing without the right people at the right time.
Speaker 2: Stage one, under 50 staff, you likely have a single operations lead wearing
every hat. Give them clear escalation paths into engineering.
Speaker 1: Stage two adds dedicated L1 agents and someone curating knowledge.
Rotating product squads for L2 keeps context fresh.
Speaker 2: By stage three you need specialists—security, infrastructure, SaaS
owners—and a service owner measuring CSAT and backlog health.
Speaker 1: Founders love roadmaps, so translate process maturity into
month-by-month wins.
Speaker 2: Month one, document services and publish runbooks for the top incidents.
Month two, launch the knowledge base and start change reviews.
Speaker 1: Month three brings problem management huddles and automated
joiner/mover/leaver workflows.
Speaker 2: After that, quarterly service reviews with finance and product keep the desk
aligned to business priorities and budgets.
Speaker 1: Call out failure modes at each stage so teams spot drift early—ownerless
runbooks, ignored dashboards, automation without monitoring.
Speaker 1: Metrics prove the desk is worth the investment. Without them, it’s just more
overhead.
Speaker 2: Track response and resolution SLAs, but also self-service deflection—can at
least a third of tickets resolve without human hands?
Speaker 1: CSAT surveys and article helpfulness scores show quality, while
cost-per-ticket and engineering hours returned show business impact.
Speaker 2: Package those results into a monthly narrative so executives keep funding
headcount and tooling improvements.
Speaker 1: With the numbers telling the story, our wrap-up can focus on reinforcing the
habits that keep the desk evolving.
Speaker 2: And bring a simple ROI one-pager to budget reviews so leaders see the cost
avoidance alongside the spend.
Speaker 1: So the playbook is simple: single intake, living knowledge base, right-sized
tooling, and people who can grow with the process.
Speaker 2: Nail those and you turn IT from a fire brigade into a service your startup
brags about in due diligence calls.
Speaker 1: Plus the metrics make future investments easier to pitch. Nothing beats
saying, "We saved 200 engineering hours last quarter."
Speaker 2: Now let’s push the pilot live and iterate weekly. Momentum is your best
stakeholder management tool.
Speaker 1: Keep an eye out for the classic pitfalls—tooling without process, dusty
runbooks, and remote teams left out of the loop—and course-correct fast.
# Narrative Outline — Scaling Support Processes
## Tasks
- [x] Chart the shift from ad hoc founder support to structured help desks and
knowledge bases.
- [x] Compare ServiceNow and Jira Service Management for growing teams.
- [x] Advise on staffing and process milestones for support maturity.
## Notes
- Narratives cover pain signals, intake design, knowledge management, tooling
trade-offs, automation, staffing and metrics.
Security Baselines Shoestring
Speaker 1: [inviting] Imagine your seed-stage startup spending more on coffee than on
security tooling.
Speaker 2: Yet the board still expects you to survive a phishing email or a stolen laptop
without dialing 911 for IT.
Speaker 1: We will decode the jargon, translate compliance checklists, and show which
controls actually buy you sleep.
Speaker 2: Think of us as your pragmatic advisor and technical translator, tag-teaming
to stretch every security dollar.
Speaker 1: [pragmatic] First, let’s level-set the threat landscape—phishing, ransomware
and accidental leaks do not wait for Series B funding.
Speaker 2: Customers know it too, which is why GDPR clauses and SOC 2
questionnaires now hit before the second sales call.
Speaker 1: A written baseline becomes the playbook you hand contractors, fractional
CISOs and auditors so everyone enforces the same guardrails.
Speaker 2: With that context set, we can prioritize the handful of controls that stop the
bleeding fastest.
Speaker 1: [focused] Start with four anchors: phishing-resistant MFA, a shared password
vault, automatic patching and resilient 3-2-1 backups.
Speaker 2: If you cannot prove who logged in, whether the laptop was healthy, or that
data is recoverable, every other control is theatre.
Speaker 1: Hardware keys for admins and $20-per-user password managers are
cheaper than the revenue lost during a forced credential reset week.
Speaker 2: Nail these basics and you are ready to treat identity as the new perimeter,
which is exactly where we go next.
Speaker 1: [analytical] Identity is the control plane, so treat Workspace or Entra ID as
the perimeter you can actually defend.
Speaker 2: Our technical translation: block legacy auth, require healthy devices, and
script joiner-mover-leaver flows so access changes within minutes.
Speaker 1: Quarterly access reviews become storytelling moments—"here’s who lost
admin rights and how we mitigated the risk."
Speaker 2: With accounts locked down, it’s time to harden the laptops and phones
people carry into coffee shops.
Speaker 1: [grounded] Devices are still where breaches begin, especially when the
team is scattered across kitchen tables and coworking hubs.
Speaker 2: Lightweight MDM like JumpCloud or Kandji enforces encryption, patch
automation and remote wipe for less than a nice lunch.
Speaker 1: Pre-built recovery kits mean a stolen laptop triggers a one-hour replacement
play, not a two-week GDPR panic.
Speaker 2: Once endpoints behave, we can tackle the SaaS sprawl and "don’t tell mom"
apps that hide outside IT.
Speaker 1: [strategic] SaaS bloat sneaks up faster than payroll, so shine a light on
every subscription and browser plug-in.
Speaker 2: Finance exports, SSO logs and discovery add-ons expose the "free" tools
bypassing MFA, logging and data retention commitments.
Speaker 1: We pair that visibility with DNS filtering—the remote-friendly firewall that
blocks malware domains before anyone clicks.
Speaker 2: With the app layer tidy, we can decide whether to build detection in-house
or rent a virtual SOC bench.
Speaker 1: [reassuring] You do not need a 24/7 internal SOC; you need trustworthy
humans on retainer who know your environment.
Speaker 2: Huntress, Arctic Wolf or Defendify drop straight into Slack with curated
alerts and human analysts translating the noise.
Speaker 1: Negotiate the playbook now—who calls whom at 2 a.m., how fast they
escalate, and what evidence they collect.
Speaker 2: Keep an internal owner accountable so the MSSP augments your team
instead of becoming an expensive scapegoat.
Speaker 1: [technical] Even on a budget we can centralise the signals that matter by
treating telemetry as our flight recorder.
Speaker 2: Wazuh, Elastic Agent or Panther Community keep costs low while Tines-style
automation enriches alerts with owner, criticality and runbook links.
Speaker 1: Prioritise identity, endpoint and cloud audit trails—the logs that tell us who
did what, where and when.
Speaker 2: Once those breadcrumbs are flowing, the culture work kicks in to make
every teammate part of the detection surface.
Speaker 1: [playful] Remember the classic "have you tried turning it off and on again?"
We weaponise that humour for patch hygiene.
Speaker 2: Scheduled reboot windows, phishing drill shout-outs and coffee vouchers for
first reporters make security feel winnable, not punitive.
Speaker 1: Publishing MFA and patch scoreboards sparks friendly competition, proving
culture change without shame.
Speaker 2: That energy sets the stage for calm incident response rehearsals instead of
panicked, once-a-year checkbox exercises.
Speaker 1: [calm] Preparation is the cheapest resilience—two-page runbooks, crisis
comms templates and a speed-dial list beat Slack archaeology at 3 a.m.
Speaker 2: Free tabletop guides from CISA or your insurer give you structure without
consultancy rates or slide decks thicker than the product roadmap.
Speaker 1: Capture lessons learned immediately so scripts, automations and contact
trees evolve alongside the business.
Speaker 2: Those notes flow straight into the roadmap we’ll walk through next, keeping
momentum without overwhelming lean teams.
Speaker 1: [motivating] Sequencing keeps the workload sane—MFA, vaulting and
inventory in the first sprint, then SOC contracts and table-tops as confidence grows.
Speaker 2: By day 60 the outsourced analysts know your escalation path; by day 90
you are iterating telemetry instead of firefighting.
Speaker 1: Wrap every sprint with metrics: MFA coverage, patch SLAs, incidents closed
internally versus escalated.
Speaker 2: Those benchmarks become the board slide that proves security spend is
disciplined, compliant and revenue-enabling.
# Narrative Outline — Security Baselines on a Shoestring
## Tasks
- [x] Prioritise essential controls such as password managers, basic MDM and zero-trust
defaults.
- [x] Explain the stakes for phishing, ransomware, compliance questionnaires and
startup-scale incidents.
- [x] Note outsourced options like lightweight SOC services and monitoring dashboards.
- [x] Connect humour and culture cues—"have you tried turning it off and on again"—to
pragmatic security hygiene.
- [x] Reinforce the 30/60/90 roadmap and board-ready metrics as the
confidence-building finale.
## Notes
- Summarise affordable security controls, outsourced SOC options, jargon decoding and
lightweight monitoring defaults.
- Bridge segments so identity leads to device hardening, SaaS hygiene feeds detection,
and culture primes incident readiness.
Series A Tool Stack
Speaker 1: [energised] Welcome to the Series A stack session—where governance
grows up without turning into enterprise theatre.
Speaker 2: Our north star is a ~$2K/month toolkit that lets Sarah pass diligence,
onboard fast and keep building product.
Speaker 1: Think of today as pressure-testing every subscription against investor
questions and customer trust requirements.
Speaker 2: And yes, we will finally settle the "serverless versus containers" debate with
actual numbers.
Speaker 1: [contextual] Series A is when the customer list suddenly includes banks,
telcos and government pilots.
Speaker 2: Example time—TechCorp just landed its first hospital client demanding
4-hour incident response, SSO for 200 seats and quarterly attestations before
green-lighting the next $2M tranche.
Speaker 1: Headcount jumps past 40, contractors flood in, and "who approved that
access" becomes a board question.
Speaker 2: I watched that TechCorp board delay funding for two months until the
policies and tools matched the promises, so we anchor on controls that scale before
cash burn does.
Speaker 1: Pause here—does this $2K map mirror your actual workflows or just vendor
demos?
Speaker 2: It becomes our rubric: identity, communications, delivery, trust, data; any
tool outside those lanes needs evidence first.
Speaker 1: [analytic] Here’s the $2.1K snapshot—identity, collaboration, delivery,
compliance and RevOps.
Speaker 2: Note the assumptions: 45 Okta seats, 30 Slack Business+ seats, 18 Zoom
hosts.
Speaker 1: Investors want to see the maths, so we show the per-seat logic and credits
applied to Vanta.
Speaker 2: Plus a path to stay inside burn modelling even when Snowflake usage
spikes.
Speaker 1: [confident] Okta is the backbone—every vendor contract we sign must land
behind its MFA wall.
Speaker 2: And the audit trail is gold; diligence teams can literally download access
reports and see policy history.
Speaker 1: Offboarding is my devil's-advocate test—if someone can still hit Slack three
days later, congratulations, you've produced a revenge thriller, not a security posture.
Speaker 2: War story: a client missed that test, and the departing PM nuked channels
on the way out—Advanced Server Access would have prevented the coda entirely.
Speaker 1: [practical] Slack Business+ plus Zoom Business is the heartbeat for deals
and delivery.
Speaker 2: Business+ is non-negotiable once you promise SSO; it also unlocks legal
hold exports.
Speaker 1: We cap Zoom hosts at 18 and rotate webinar add-ons instead of buying a
permanent package.
Speaker 2: Finance gets visibility on renewal owners so there are no "surprise
auto-renew" posts in #announcements—that message has ended more Series A rounds
than failed demos.
Speaker 1: [methodical] Jira, Confluence and Opsgenie stay as a bundle so we can track
the full change lifecycle.
Speaker 2: Opsgenie closes the loop—alerts, acknowledgements and retros all
exportable for Vanta evidence.
Speaker 1: Only tech leads hold Jira admin rights; everyone else inherits projects via
Okta groups.
Speaker 2: We also note the 50-seat threshold when Atlassian pricing bumps by ~15%,
so finance isn’t blindsided.
Speaker 1: [urgent] The incident workflow slide is our promise to that hospital—Level 1,
2 and exec responders ready inside four hours.
Speaker 2: I run quarterly tabletops where customer success, legal and engineering
swap roles; the evidence PDF lives in Confluence for diligence teams.
Speaker 1: Devil's advocate check—who actually declares the incident and who calls
the customer?
Speaker 2: When those names are blank, investors smell theatre; when they’re
rehearsed, they see operational maturity.
Speaker 1: [assured] Vanta—or Drata if you prefer—basically becomes the fractional
compliance officer.
Speaker 2: It hoovers up evidence from Okta, AWS, Jira and GitHub, so we’re not
screenshotting configs every quarter.
Speaker 1: The spend looks steep until you compare it to $200K consultants or a
full-time security hire.
Speaker 2: War story: a fintech client paused a million-dollar deal until they shared their
Vanta readiness report—questionnaires vanished overnight after that badge went live.
Speaker 1: Tools handled—now stress-test architecture costs before finance does the
math.
Speaker 2: Cost, latency, staffing, risk, credits; if those five pillars wobble, the rest of
your board narrative collapses fast in seconds.
Speaker 1: [forward-looking] Data is the new argument—finance, RevOps and product
need the same truth source.
Speaker 2: Fivetran Lite pulls in SaaS data, Snowflake stores it cheaply and dbt applies
the business rules.
Speaker 1: We pause warehouse compute overnight to keep the bill under $80 and
alert if credits spike.
Speaker 2: Reverse ETL comes later, but we already note the vendor shortlist so the
roadmap feels intentional.
Speaker 1: [comparative] Let’s crunch the infrastructure choice—serverless lands
around $380 in platform fees.
Speaker 2: Think of the fintech API handling 80M monthly transactions; Lambda flexes
with market spikes while containers would sit idle 23 hours a day.
Speaker 1: Devil's advocate question—are we chasing Kubernetes because investors
said "enterprise", or because the workloads truly need it?
Speaker 2: Until you see 100M requests, brutal cold starts or custom networking, stay
serverless and pour the savings into customer-facing capability.
Speaker 1: [decisive] When cost per 1K invocations creeps past $0.60 or cold starts
breach 150ms, the math flips.
Speaker 2: GrowthCo hit both thresholds; six weeks on Fargate cut request spend 40%
but they also hired a $160K platform engineer.
Speaker 1: Devil's advocate—do we have Terraform discipline and security reviews
ready, or are we just buying shinier compute?
Speaker 2: Document that full TCO in the board pack so no one forgets the people cost
hidden in the migration.
Speaker 1: [evaluative] Vendor selection at Series A is less about features and more
about security hygiene.
Speaker 2: My scorecard starts with SSO, SCIM, audit trails and export guarantees
before we ever discuss UI polish.
Speaker 1: Devil's advocate asks: can we downgrade or exit without months of contract
lawyering?
Speaker 2: Talk to references under your regulator; I’ve had startups dodge
seven-figure liabilities because a peer warned them about missing SOC carve-outs.
Speaker 1: Deep breath; tooling and architecture are set, now translate them for the
money people.
Speaker 2: Risk removed, revenue enabled, downgrade options, human cost—hit those
beats and investors skip mythical hires entirely.
Speaker 1: [strategic] When we brief investors, we tie each tool to a risk retired or
revenue lever unlocked.
Speaker 2: Okta kills account sprawl, Vanta prevents six-figure consulting and Atlassian
proofs our change discipline.
Speaker 1: We also show downgrade paths—pause Fivetran, drop Opsgenie seats—if
growth slows.
Speaker 2: When someone says "why not hire one person to do it all?", I show the
fictional salary for a security+RevOps+data unicorn and let the silence do the work.
Series B Enterprise Stack
Speaker 1: [confident] Welcome to the Series B stack lab—where the tooling budget
finally catches up with enterprise expectations.
Speaker 2: We are working with a ~$20K/month run rate that keeps investors calm
while clearing customer due-diligence checklists.
Speaker 1: Everything today connects pipeline integrity, service reliability and audit
evidence into one story.
Speaker 2: Grab the worksheet template—we'll keep translating architecture choices
into dollar impacts as we go.
Speaker 1: The jump to Series B is about scale—200 people, multi-region support
windows, and customers who read every appendix of the MSA.
Speaker 2: Those customers expect 24/7 coverage, verifiable SOC 2 controls and
contractual uptime remedies.
Speaker 1: Investors simultaneously expect you to model spend 18 months out, so
every SKU needs a forecast line and a justification.
Speaker 2: That's why the stack becomes an enterprise nervous system instead of a
patchwork of founder credit-card tools.
Speaker 1: Picture a three-layer reference architecture—revenue, service, and
trust—glued together by automation.
Speaker 2: Salesforce Enterprise with CPQ captures every entitlement and renewal
clause; when pricing changes, downstream systems inherit it instantly.
Speaker 1: ServiceNow owns operational truth: incidents, changes, and customer
service cases with audited hand-offs.
Speaker 2: A Snowflake lakehouse plus dbt models bring both worlds together for
finance and customer health dashboards.
Speaker 1: Add CLM for legal workflows and a SIEM/EDR pairing so every action shows
up in the audit trail.
Speaker 1: Here’s the budget: eight categories totaling roughly twenty grand a month.
Speaker 2: Salesforce plus CPQ is the lion’s share at $7.2K because it locks ARR, usage
metrics and renewal co-terms into one system.
Speaker 1: ServiceNow adds $3.9K for ITSM and CSM agents—pricey, but it keeps
regulated customers out of your inbox.
Speaker 2: Security, integration, CLM, RevOps tooling and a 10% buffer round it out so
nothing breaks when you add seats or new geographies.
Speaker 1: Keep this table in the worksheet; we’ll plug real seat counts and unit costs
into it during the exercise.
Speaker 1: Integrations make or break the Series B stack—start with Salesforce and
ServiceNow sharing account hierarchies and case numbers.
Speaker 2: When a monitored service breaches an SLA, ServiceNow auto-creates a
case, pushes the alert to PagerDuty and mirrors the escalation inside Salesforce.
Speaker 1: Change approvals from ServiceNow write back into the Salesforce
opportunity so renewals stay aligned with production reality.
Speaker 2: Meanwhile Panther ingests ServiceNow audit trails so the security team can
see who touched what without logging into three consoles.
Speaker 1: Okta’s SCIM feeds keep user provisioning and least privilege tidy across
both platforms.
Speaker 1: Contract lifecycle management is the unsung hero when legal reviews start
stacking up.
Speaker 2: Ironclad gives sales reps clause playbooks tied to industry and region so
they stop emailing legal for every redline.
Speaker 1: ServiceNow’s Vendor Risk module plugs in due-diligence artefacts, and
NetSuite consumes the executed contract for revenue recognition.
Speaker 2: Snowflake picks up those contract events to drive renewal forecasts and
ARR dashboards.
Speaker 1: With DocuSign CLM in the mix, you get audit-grade history of every version,
approver and obligation.
Speaker 1: Security spend isn’t optional at this stage—you have auditors and enterprise
CISOs reading your runbooks.
Speaker 2: SentinelOne feeds telemetry into Panther so you meet PCI and Essential
Eight retention requirements without buying extra storage à la carte.
Speaker 1: Drata hoovers up evidence from Okta, AWS, ServiceNow and Jira, which
means SOC 2 refreshes become continuous rather than annual heroics.
Speaker 2: Whistic’s questionnaire exchanges deflect bespoke security forms and keeps
customer trust teams sane.
Speaker 1: Budget line item: 80 hours of a specialist partner to tune detections and
response playbooks—you will not get this right on your own the first time.
Speaker 1: Let’s unpack the worksheet—it’s five tabs so finance, IT and GTM leaders
stay in sync.
Speaker 2: Inventory captures system owners, renewal dates and SKUs so nothing
auto-renews in the shadows.
Speaker 1: Seats & tiers records current counts plus the trigger that forces an
upgrade—headcount, compliance or product launch.
Speaker 2: Projects tracks partner statements of work so you can capitalise or amortise
where appropriate.
Speaker 1: Scenario levers and risk offsets close the loop, showing how investments
avoid penalties or headcount hires.
Speaker 1: The levers tab is where your plan lives or dies.
Speaker 2: Add a headcount scenario and watch Salesforce and ServiceNow costs
adjust automatically.
Speaker 1: When a new SOC 2 customer appears, the SIEM storage and support agents
increase; the worksheet calculates the hit instantly.
Speaker 2: If you spin up EMEA operations, Workato recipes and DocuSign compliance
packs switch on—again, the formulas push the delta into the summary.
Speaker 1: Don’t forget to document savings too; automation or product sunsets should
feed the buffer instead of disappearing.
Speaker 1: For the workshop, we’ll map your current stack to this reference model.
Speaker 2: Populate the worksheet with real owners, renewal dates and seat
counts—no guesses.
Speaker 1: Run best and worst ARR cases with a 15% contingency so the board sees
you’ve pressure-tested the plan.
Speaker 2: Document the top integration risks and the mitigation you’ll fund with that
buffer.
Speaker 1: Close with a two-slide executive summary: one for spend, one for risk
posture—it becomes your board pack insert.
# Narrative Outline — Series B Enterprise Stack
## Tasks
- [x] Describe the ~$20K/month enterprise-grade stack with Salesforce, ServiceNow and
SIEM.
- [x] Introduce contract lifecycle management additions and integration considerations.
- [x] Provide a worksheet concept for modelling the expanded costs.
## Notes
- Explain the Series B enterprise tooling mix, integrations and cost modelling worksheet.
Shadow It Low Code Experimentation
# Slide 1 — Shadow IT and Low-Code Experimentation
Speaker 1: [energetic] Shadow IT is not a villain; it's a neon sign flashing "your teams
are hungry to solve problems."
Speaker 2: And banning every unsanctioned app just drives the experiments deeper
underground, with zero telemetry.
Speaker 1: Our job tonight is to channel that curiosity into a safe runway—guardrails,
not handcuffs.
Speaker 2: Because when you give people space to prototype responsibly, innovation
and compliance can actually coexist.
# Slide 2 — Why shadow IT happens
Speaker 1: Product managers see customer churn in real time and reach for whatever
no-code tool plugs the hole fastest.
Speaker 2: Meanwhile the official backlog is negotiating infrastructure upgrades, so
"just wait" feels like career suicide.
Speaker 1: Vendors don’t help—they wrap admin rights in cheerful free trials and
suddenly payroll data lives in a hobby project.
Speaker 2: It's human nature—if the official solution takes 6 months and the
workaround takes 6 minutes, guess which one wins?
Speaker 1: And lending out an "innocent" workaround is like handing over your car keys
for a corner-store run that somehow ends in Vegas selfies.
# Slide 3 — Upside of sanctioned tinkering
Speaker 1: When we bless experimentation, prototypes become user research assets
instead of rogue spreadsheets.
Speaker 2: Remember that ops dashboard? They pulled support tickets, customer
health scores, and renewal dates into one view that saved two hours of manual
reporting every day.
Speaker 1: Engineering would still be scoping the request; the team shipped it over a
weekend and proved the value instantly.
Speaker 2: Plus, citizen developers learn to speak API and process in the same
sentence—it’s career development wrapped in delivery.
Speaker 1: And when experiments are visible, finance finally gets data to justify the
headcount or tooling upgrades the team has been whispering about.
# Slide 4 — Risk: access sprawl and data leakage
Speaker 1: The dark side is permissions that balloon faster than anyone can track.
Speaker 2: Suddenly marketing’s prototype syncs customer PII into someone’s personal
Google Drive because the connector shipped with "full access".
Speaker 1: And here’s the kicker—no one realizes until the first security audit and
you’re explaining the phantom admin account.
Speaker 1: Incident responders then chase ghosts—no runbooks, no system owner, just
an error email at 2 a.m.
Speaker 2: Meanwhile, the "free" tier quietly locks in your data—premium exports,
surprise licensing, and compliance gaps galore.
Speaker 1: And remember, many contracts and privacy laws explicitly forbid moving
data to unsanctioned systems. Ignorance won’t save you during a GDPR or SOX review.
# Slide 5 — Cautionary tale: the Slack admin summer
Speaker 1: True story: an intern built a workflow bot to celebrate customer renewals.
Speaker 2: Adorable—until they ticked "Workspace Admin" for every channel lead
because "permissions are annoying".
Speaker 1: Within days a curious contractor explored the new menu and archived the
finance history channel.
Speaker 2: Cue frantic tickets to Slack support, legal drafting disclosure emails, and the
CTO spending Sunday rebuilding export logs. Enthusiasm needs seatbelts.
Speaker 1: Also, three years of quarterly reports vanished—the CFO's expression was...
memorable.
# Slide 6 — Access guardrails that scale
Speaker 1: The fix is to engineer permission hygiene into the platform.
Speaker 2: Start with role blueprints—builder, reviewer, auditor—and make them the
only options in production tenants.
Speaker 1: Provision through SSO groups so offboarding a leaver takes seconds and
leaves an audit trail.
Speaker 2: And yes, insist on data classification labels that literally stop exports of
customer health scores or payroll files.
Speaker 1: Any emergency elevation should ping the owner and expire automatically;
we treat admin rights like temporary visas.
Speaker 2: Because permanent admin is forever—and auditors have memories like
elephants wearing spreadsheets.
# Slide 7 — Safe sandboxes for experimentation
Speaker 1: Guardrails don’t mean boring. Give teams playgrounds with sanitized data
and disposable connectors.
Speaker 2: Picture this: finance gets a dedicated Tableau workspace, anonymized
revenue data, connectors to approved databases, and templates that auto-expire after
90 days.
Speaker 1: Golden templates save hours—they come preloaded with logging, naming
conventions and "who to call" notes.
Speaker 2: Also, route integrations through service accounts so when someone leaves,
production tokens aren’t tied to their inbox.
Speaker 1: Bonus points for running quarterly hack nights with platform engineers
coaching—experimentation becomes a team sport, not a secret hobby.
# Slide 8 — Lightweight governance rituals
Speaker 1: Process-wise, start with a three-question intake form: what problem does
this solve, what data does it touch, and who owns it when things break?
Speaker 2: Then schedule a fortnightly thirty-minute huddle where platform, security
and the builders review anything new.
Speaker 1: Document outcomes in a living catalogue so support knows what exists and
what tier of help it gets.
Speaker 2: Feed notable risks into the enterprise register; executives hate surprises,
but they love trendlines that show you’re steering the ship.
# Slide 9 — Observability and assurance
Speaker 1: If experimentation is invisible, risk teams default to "no". So wire these
platforms into your logging stack.
Speaker 2: Track the basics—"47 active low-code apps, 12 orphaned flows closed last
quarter, 4-hour average response for connector issues"—so you can prove stewardship
with data.
Speaker 1: Run tabletop drills where a connector token is compromised. Watch who
notices, who has the keys, and how fast you respond.
Speaker 2: Then teach those lessons during onboarding so newcomers learn the
approved way to tinker from day one.
# Slide 10 — How shadow IT surfaces
Speaker 1: Detection isn’t just gut instinct; network monitoring lights up when new
SaaS domains start siphoning data.
Speaker 2: Finance helps too—mystery $49 charges and annual renewals on personal
cards are the canary in the coal mine.
Speaker 1: CASB dashboards and identity logs show which OAuth grants appeared
without going through the service catalog.
Speaker 2: When someone raises a hand about a rogue tool, celebrate the find first,
then partner on the fix. Curiosity beats cover-ups.
# Slide 11 — Roles, traits and career pathways
Speaker 1: The stewards here are often platform engineers or automation leads who
love building tooling as much as guardrails.
Speaker 2: They partner with business technologists—the ops analyst who can
storyboard a process and translate it into a safe low-code pattern.
Speaker 1: Governance analysts sharpen their empathy, learning to say "yes, if" and
maturing into risk leaders who are still pro-experimentation.
Speaker 2: And the curious citizen developers? With mentoring they grow into solution
architects who mentor the next wave of tinkerers.
# Narrative Outline — Shadow IT and Low-Code Experimentation
## Tasks
- [x] Describe the benefits and risks of letting teams prototype with no-code and
low-code tools.
- [x] Include the humorous story about the intern who accidentally made everyone a
Slack admin.
- [x] Offer guardrails to empower experimentation without losing control of data or
access.
## Notes
- Discuss empowering teams with no-code while avoiding chaos, accidental
over-permissioning, and surprise compliance gaps.
- Narrative now emphasises responsible experimentation, logging, vendor lock-in
awareness, detection tactics, and career pathways for citizen developers.
Startup Budgeting Finops
Speaker 1: [upbeat] Welcome to our deep dive into budgeting and FinOps for Sarah's
start-up.
Speaker 2: We're here to prove that disciplined cost management can coexist with
ambitious product roadmaps.
Speaker 1: Think of this session as a playbook for stretching every credit without
throttling innovation.
Speaker 2: And we promise to keep it tactical—no enterprise finance jargon required.
Speaker 1: [curious] First, let's anchor what participants should walk away with.
Speaker 2: They need a FinOps mindset sized for fewer than 50 people, not a Fortune
500 bureaucracy.
Speaker 1: We also connect tooling spend directly to runway conversations so finance,
product and investors see the same numbers.
Speaker 2: Finally, everyone practices spotting optimisation levers before renewals lock
in waste.
Speaker 1: [thoughtful] A FinOps mindset in year one starts with acknowledging cash is
your scarcest resource.
Speaker 2: Exactly—so we lay out guardrails before Sarah automates every workflow or
signs annual commits.
Speaker 1: Documenting cost taxonomy sounds dull, but it stops engineering and
finance from arguing over which budget a new tool hits.
Speaker 2: And those living forecasts? They're the proof investors need that the team is
steering spend deliberately.
Speaker 1: [analytical] When we map runway, we anchor on a simple burn formula that
everybody can recite.
Speaker 2: Then we separate must-have spend from experiment budgets so product
bets don't quietly cannibalise payroll.
Speaker 1: Calling out contractual cliffs keeps Sarah from being surprised by
auto-renewals or seat minimums.
Speaker 2: And the shared dashboard keeps stakeholders aligned on which customers
and features actually drive the bill.
Speaker 1: [energised] Credits can feel like free money, but the expiry dates creep up
fast.
Speaker 2: That's why we inventory every cloud provider perk and match workloads
carefully.
Speaker 1: Low-risk environments soak up those credits first while we tune rightsizing
and scheduling tactics.
Speaker 2: Budget alerts at 60, 80 and 100 percent stop panic fire drills by catching
drift early.
Speaker 1: [practical] Monitoring usage is the boring hero work that keeps costs tame.
Speaker 2: Centralising billing exports means Sarah stops copy-pasting invoices at
midnight.
Speaker 1: Tags and labels turn raw bills into insight—suddenly you know the growth
team triggered last month's spike.
Speaker 2: Weekly digests and variance triggers create a rhythm so nobody is surprised
by the finance meeting.
Speaker 1: [engaging] Here's the concrete spend drill we run in workshops.
Speaker 2: Learners see how credits offset AWS bills, while cash still flows to
collaboration, monitoring and support tools.
Speaker 1: The contingency line normalises setting aside 10 percent for surprises
instead of hoping they never happen.
Speaker 2: We deliberately show the total cash outlay so teams link the numbers back
to runway, not just accrual accounting.
Speaker 1: [directive] During the exercise, we ask each team to clone the drill with their
own stack assumptions.
Speaker 2: As they tweak seat counts and usage, the guardrails force trade-offs—keep
the SOC tool or hire a contractor?
Speaker 1: The optimisation lever per tool becomes an action list for the next quarter.
Speaker 2: It also builds muscle memory for renegotiating or automating before the
finance team has to step in.
Speaker 1: [cautionary] We also spotlight the red flags Sarah will meet in real life.
Speaker 2: Multi-year deals feel flattering, but at pre-Series A they usually mortgage
optionality.
Speaker 1: Auto-renewals are sneaky, so we model calendar holds as part of the FinOps
ritual.
Speaker 2: And when founders ignore chargeback data, they lose credibility fast with
both finance leads and investors.
Speaker 1: [confident] All this work feeds directly into investor conversations.
Speaker 2: Monthly scorecards show spend versus forecast and how many credits
remain, signalling control.
Speaker 1: When Sarah can say "rightsizing bought us two extra months of runway,"
the room pays attention.
Speaker 2: Inviting observers to FinOps reviews turns a potential grilling into a
collaboration ahead of the next raise.
Speaker 1: [motivating] We close with an action plan Sarah can run immediately.
Speaker 2: Weekly cost reviews with engineering and finance build the drumbeat.
Speaker 1: The central ledger for credits, renewals and owners stops information from
living in someone's inbox.
Speaker 2: Revisiting guardrails at each funding milestone keeps FinOps aligned with
the pace of growth instead of blocking it.
# Narrative Outline — Budgeting and FinOps for Start-ups
## Tasks
- [x] Show how to monitor usage, stretch cloud credits and forecast burn tied to tooling.
- [x] Design a short exercise calculating total monthly stack spend.
- [x] Connect financial literacy to investor conversations about runway.
## Notes
- Plan the FinOps budgeting activity and cloud credit optimisation talking points.
Vendor Management Rhythms
# Vendor Management Rhythms — Narrative
High-growth teams lean on vendors to fill capability gaps long before they can hire
specialists. That leverage only works when everyone is working to the same beat.
Rituals create shared expectations about responsiveness, decision velocity, and quality
gates. Without them, a managed service provider can unknowingly slow the roadmap or
miss critical context about upcoming launches. This segment frames cadence as a
strategic control system rather than polite catch-ups.
We also remind founders that rhythms reduce emotional escalations. When partners
know there is a weekly forum to raise blockers, they do not resort to panicked emails at
midnight. When the leadership team sees trend data every month, they can intervene
early instead of issuing broad-brush ultimatums. Process gives both sides psychological
safety to be candid about risks.
## Establishing cadence rituals
Coming out of the "why rhythms matter" segment, we hand learners a concrete
operating drumbeat they can deploy on Monday. We outline a three-tier rhythm that
keeps partners plugged into strategy and execution. Weekly operations syncs are
deliberately short and tactical: review ticket queues, note any SLA breaches, and
unblock near-term tasks. Monthly service reviews go a level higher to interrogate trend
lines, incident learnings, and improvement experiments. Quarterly business reviews
reconnect the relationship to company strategy, budgets, and roadmap shifts.
Emphasise that cadence is anchored to meaningful triggers. Align the weekly call
before your release deploys, schedule the monthly review after financial close so real
cost data is available, and run the quarterly session ahead of contract renewal
windows. When rituals connect to existing beats, the right stakeholders attend
prepared instead of treating meetings as optional. Close every meeting by logging
owners, deadlines, and notes in the shared workspace so momentum compounds
instead of evaporating between calls.
## Running the weekly ops sync
The weekly sync should feel like a high-signal stand-up, not a status monologue.
Encourage learners to cap the session at 30 minutes with a three-slide deck:
performance snapshot, escalations, and upcoming changes. Assign owners to every
yellow or red metric before the call ends and log due dates in the shared tracker.
Anything without a name or deadline will resurface as an incident later.
Use the final minutes for a "no surprises" scan. Ask explicitly about launches, audits,
marketing campaigns, or staffing changes that could impact capacity. Offer a concrete
prompt: "We're launching the Black Friday campaign next week and expect 10x
traffic—can your monitoring handle the alert volume?" That habit gives vendors
permission to flag constraints before they become outages and reinforces that the
start-up wants partnership, not heroics. It also prevents the 3 a.m. vendor panic call
that starts with "We didn't know you were deploying today...".
## Building a meaningful scorecard
Scorecards convert gut feel into shared evidence. Coach learners to combine SLA/SLR
metrics—response time, resolution time, uptime—with adoption and satisfaction data
such as NPS from internal stakeholders or product usage analytics. Leading indicators
like backlog age, staffing ratios, and change failure rate provide early warning signals
before contractual breaches occur.
Stress the importance of data hygiene. Partners should pull metrics from a single
source of truth, snapshot them before the review, and annotate anomalies. Colour
coding helps executives parse quickly, but it must link to predefined thresholds that
automatically trigger escalation or executive awareness. The scorecard becomes a
living document for accountability.
Show an example template to make the abstract concrete: availability ≥99.9% stays
green, 99.5–99.89% is yellow, anything lower turns red. Pair that with first-response
targets (green <15 minutes for P1 tickets), change failure rate bands (<10% green,
10–20% yellow), backlog age for critical tickets (<3 days green), stakeholder NPS (≥50
green), and compliance evidence status. When facilitators can point to six crisp metrics
with thresholds, learners understand how to translate principles into dashboards.
## Monthly service review ritual
Monthly reviews zoom out far enough to connect operational health with strategic
priorities. Encourage facilitators to lead with trend lines: three months of SLA
performance, cost variance, and satisfaction scores. From there, walk through
incidents—what we learned, how remediations are tracking, and whether they require
executive support.
Capacity planning is a key section. Challenge vendors to bring forward-looking staffing
plans, upcoming maintenance windows, and assumptions about ticket volumes. Close
the review by committing to two or three improvement experiments, assigning owners,
and noting when results will be assessed. That loop converts the meeting from
reporting theatre into a driver of continuous improvement.
Do not forget to celebrate the wins. A quick shout-out for the vendor engineer who
crushed the migration or the analyst who spotted a fraud pattern keeps the relationship
human and motivates continued excellence.
## Make-vs-buy as a living decision
Start-ups often make an initial outsourcing decision under extreme time pressure.
Remind learners that the calculus shifts as product-market fit solidifies, customer
expectations rise, and internal capabilities mature. A quarterly make-vs-buy checkpoint
keeps leaders honest about whether the vendor still unlocks speed or has become drag.
Walk through the dimensions: total cost of ownership (subscription, integration, shadow
teams, compliance overhead), strategic control (IP sensitivity, customer intimacy,
regulatory obligations), and risk posture (single points of failure, vendor financial
health, data residency). Encourage teams to set quantitative thresholds—like customer
volume or margin targets—that trigger formal RFPs or insourcing investigations.
Pair the framework with contrasting case studies so learners can see the decision in
different domains. Alongside payments, explore customer support: adopting Zendesk
gets you macros, analytics, and AI triage overnight, while building an internal support
organisation requires hiring, coaching, and tooling for QA. The make-vs-buy answer can
shift over time; maybe you start with Zendesk to launch fast, then insource tier-two
support once ticket complexity justifies bespoke workflows.
## Stripe versus build-your-own payments
Use the payments example to make the framework tangible. Stripe lets a lean team
accept money quickly with globally resilient infrastructure, built-in fraud tooling, and
compliance coverage. The trade-off is ongoing transaction fees and limited influence
over the roadmap. Building in-house grants total control but requires hiring specialised
engineers, gaining PCI certification, and running 24/7 monitoring from day one.
Invite learners to map the four lenses: speed to market, cost structure, control, and
risk. Highlight that "cost" is more than fees—it is also opportunity cost of delayed
launches. Similarly, "control" includes the ability to adapt to local regulations or
bespoke checkout flows. Close by asking the cohort when they would trigger a
revisit—perhaps crossing $100M GMV or expanding into complex billing models.
Prompt discussion with a forward-looking question: if Stripe announced a material price
hike tomorrow, which leading indicators would tell you it's time to diversify payment
providers before customers feel pain?
## Documentation and accountability habits
Documentation is the connective tissue that keeps vendor rhythms effective as teams
grow. Reinforce that every meeting produces a shared note: agenda, decisions, owners,
and deadlines. Store artefacts in a central workspace alongside scorecards, contracts,
runbooks, and escalation matrices. That repository becomes the onboarding kit for new
hires and a safeguard during audits or fundraising.
Encourage lightweight automation. Integrate the action log with your ticketing tool or
CRM so reminders fire without manual chasing. Use templated scorecards and meeting
notes to reduce admin overhead. The goal is to make good governance the default
path, not additional labour.
Remind facilitators that future-you will thank present-you for taking notes—future-you
is notoriously impatient with mystery decisions.
## Key takeaways for the cohort
Wrap the segment by connecting rituals to resilience. When vendors share the same
cadence as the core team, surprises shrink and response times improve. Scorecards
turn debates into collaborative problem solving. A living make-vs-buy framework
ensures the relationship continues to serve strategy rather than legacy decisions.
Leave learners with an action plan: schedule the next three vendor touchpoints, refresh
the scorecard template, and document the thresholds that would trigger an insourcing
review. These steps show that governance can be lightweight yet powerful when it is
intentional.
Close with a gut-check question: could a new team member understand your vendor
relationships from the documentation alone? If not, the rhythms outlined here will
highlight where to invest next.
## Building a vendor security muscle
Security diligence cannot be outsourced entirely to procurement. Coach learners to
treat vendor assessments as ongoing hygiene: request SOC 2 or ISO 27001 reports
annually, review penetration-test summaries, and map each control to the data the
vendor actually touches. Pair compliance evidence with practical walkthroughs of how
encryption keys are managed, how access is revoked when staff leave, and how
incident notifications will flow to your team.
Encourage startups to run joint tabletop exercises. Simulate a compromised credential
or data-exfiltration alert to confirm who leads, who communicates, and how regulators
or customers are notified. These rehearsals expose gaps in logging, monitoring, or
contractual commitments. Fold the outputs into the same scorecards that track uptime
so security posture has equal visibility.
## Negotiating contracts that protect momentum
Contracts are operating tools, not just legal formalities. Help learners differentiate
service-level agreements (SLAs) that commit to performance and service-level reports
(SLRs) that provide transparency. Push for clear remediation timelines, service credits
tied to business impact, and escalation ladders that reach executives when targets are
missed.
Include exit strategies in the negotiation checklist. Define how data is exported, how
knowledge transfer occurs, and how long the vendor will support your migration. Cap
annual price uplifts and require advance notice for material changes. When founders
see contracts as living documents aligned to their rhythms, they negotiate clauses that
keep partners responsive instead of adversarial.
## Evaluating cultural fit before you sign
Cultural fit sounds squishy, but it dictates execution speed. Encourage founders to meet
the delivery leads, project managers, and senior ICs who will work with them daily.
Observe how the vendor runs stand-ups, documents decisions, and handles
retrospectives. If their operating cadence feels slower or more hierarchical than yours,
that friction will surface the first time you need a hotfix on a weekend.
Suggest trial sprints or limited-scope pilots to test collaboration chemistry safely. Track
responsiveness to Slack pings, clarity of written updates, and willingness to share bad
news quickly. Those signals matter as much as price because they predict whether the
vendor can blend into your existing rituals without constant policing.
## Preparing for vendor crises
Even the strongest vendor relationship will experience a wobble. Coach learners to
pre-build an incident response playbook shared across organisations: who is on the
escalation ladder, which Slack or Teams channel lights up first, and how decisions are
documented in the heat of the moment. Align on authority to pause deployments, issue
customer communications, and pull in legal or compliance.
Encourage quarterly simulations that mirror their worst nightmares: outage during peak
season, security breach, or sudden vendor staff attrition. After each drill, capture
lessons learned and plug them into scorecards and retrospectives. The goal is to reduce
reaction time when a real crisis hits and keep leadership confidence high even under
pressure.
# Narrative Outline — Vendor Management Rhythms
## Tasks
- [x] Outline lightweight cadence meetings and scorecards for outsourced partners.
- [x] Discuss the Stripe versus build-your-own payments decision point.
- [x] Encourage documentation habits that keep partners accountable.
- [x] Cover ongoing vendor security assessments and joint tabletop drills.
- [x] Summarise contract negotiation guardrails including exits and penalties.
- [x] Highlight cultural fit signals and pilot rituals before commitment.
- [x] Prepare crisis management playbooks and rehearsal cadences.
## Notes
- Detail cadence rituals, scorecards and make-vs-buy considerations for vendors.
