Due Diligence Prep Workflow

A DD-ready data room that lives in sync with your ops, not a 2-week scramble after a term sheet.

Updated 2026-04-18
Tycoon solution

AI CFO + AI COO maintain a DD-ready data room year-round. Every vendor contract auto-archived at signing. Every IP assignment tracked from day one. Cap table stays current in Carta/Pulley. Customer data aggregated monthly. Security posture documented continuously. When a term sheet lands, you have 95% of the checklist already assembled — the raise closes in 4 weeks, not 12.

How it runs

  1. Year-round data room maintenance

    Tycoon's DD data room in DocSend/Vaulto updates continuously: new contracts archived at signature, new hires' IP assignments tracked at onboarding, new customer logos added to the customer list, monthly financials dropped in the financials folder. Not a scramble — a living system.

  2. Checklist mapping to VC/acquirer standard

    When the term sheet arrives, AI CFO maps the VC's DD checklist (pulled from their intake or a shared template) against your existing data room. Green = already in the room. Yellow = partial, needs assembly. Red = missing, needs new work. Typical starting point: 75-85% green, 10-15% yellow, 5-10% red.

  3. Cap table scenarios

    AI CFO runs cap table scenarios in Carta/Pulley: pre/post money at the proposed terms, founder + employee dilution across current round + next 2 rounds, option pool sizing for the expected hire plan, liquidation waterfall under 3 exit scenarios. All exportable as a DD-ready doc with math shown.

  4. Customer concentration analysis

    Stripe + HubSpot data aggregated by customer: ARR, contract length, churn risk, concentration (top 10 %, top customer %). DD teams always ask — your answer is ready with source data, not a hand-wavy estimate. Anonymized version for early-stage VCs, named for term-sheet-stage.

  5. Legal and IP clean-up

    AI COO runs the legal checklist: every contractor has a signed PIIA, every employee has an IP assignment, every major vendor has an MSA with IP and data terms, trademark/copyright filings are current, founder IP was properly assigned to the company. Gaps identified early, so your lawyer fixes 5 things instead of 25.

  6. Security and compliance posture

    For SaaS companies: SOC 2 evidence (if you have it), security policies, incident history, privacy posture (GDPR, CCPA), data residency. For consumer: privacy policy versioning, DMCA compliance. AI CTO maintains the security artifacts in Vanta or Drata year-round.

  7. DD Q&A response

    During active DD, questions come in waves. AI CFO + AI COO draft responses pulling from the data room with source links. Founder reviews and ships in hours instead of days. Nothing gets stuck waiting for 'I'll pull that and get back to you'.

Who runs it

  • hire/ai-cfo
  • hire/ai-coo

What you get

  • DD starts 85% complete on day 1 of term sheet
  • Raise closes in 3-5 weeks instead of 8-14
  • Legal bill drops 50-70% (lawyer reviews, not reconstructs)
  • Zero last-minute 'I can't find that contract' crises
  • Cap table scenarios at any moment, not a 2-day modeling exercise
  • Compounding advantage: same system serves Series A, B, acquisition
  • Founder answers DD questions in minutes, not wait-till-Monday
FAQ

Frequently asked questions

Clear answers about wallet credit, usage, subscriptions, and how Tycoon charges for work.

I'm pre-seed — isn't this massive overkill for my stage?

At pre-seed the data room is tiny (incorporation docs, founder IP, maybe 2-3 contracts) but the habit is what compounds. Founders who run this workflow from day one spend 4 hours total on DD at their seed round. Founders who don't spend 40-80 hours. The marginal effort at pre-seed is near zero because there's almost nothing to maintain; you're just putting things in the right folder as they happen. The payoff shows up 12-18 months later when it saves you a month on your seed raise.

What about DD for acquisition, not fundraising? The checklists are different.

80% overlap with fundraising DD — same financials, same legal/IP, same customer data. The extra 20% for acquisition: employment retention packages, customer assignment clauses in contracts, tech integration feasibility, PII handling for migration, employee option acceleration scenarios. AI COO has a separate checklist template for acquisition DD that extends the fundraising one. Most founders who sell report that the data room they built during their Series A saved them 60% of time at exit.

Can it handle international DD — FIRPTA, foreign entity structure, VAT registration, GDPR?

Yes, with the same caveat as tax prep: international adds real complexity. Tycoon handles the collection (foreign entity docs in the data room, GDPR DPA with all vendors, VAT registrations tracked per country, treaty elections documented). The strategy questions — is your UK subsidiary properly structured for the acquirer? does your Irish entity create PE issues? — need a cross-border lawyer. Tycoon makes their job easier by having the underlying data clean and findable.

Our customers have NDAs — we can't share their names. How does that work?

Customer DD has three tiers: anonymized (logos replaced with 'Fortune 500 fintech', revenue bands), pseudonymized (customer ID only, with a separate key held by founder), and named (post-term-sheet, under mutual NDA). AI CFO prepares all three versions. Early VCs get anonymized. Term-sheet-stage gets pseudonymized + references. Closing gets named under NDA. The named version is the same data with a different rendering — you decide who sees what based on where the conversation is.

What about ongoing DD updates during a 4-week closing window — things change fast.

This is where 'living data room' beats 'scramble'. During closing, AI CFO runs a weekly 'data room freshness' check: new customers added, financials rolled forward, any new contracts or hires included. VCs get notified when anything material changes, so there's no 'we forgot to tell you about the big new customer you signed Tuesday' surprise. Closes feel coordinated instead of chaotic.

Related resources

Role

AI CFO | Hire Your AI CFO Today

Hire an AI CFO that runs cash flow, pricing, models, and investor updates. Direct by chat. For founders who'd rather ship than build spreadsheets.

Role

AI COO | Hire Your AI COO Today

Hire an AI COO that runs operations, hires more AI, manages vendors, and closes loops. Direct by chat. The ops leader who keeps your entire company running clean.

Workflow

Fundraising Pipeline on Autopilot | Tycoon Workflows

Target list, warm intros, deck versioning, investor updates, and data room — a CRM-grade raise process without a BD hire.

Workflow

Legal Document Generation on Autopilot | Tycoon Workflows

NDAs, MSAs, DPAs, Terms of Service, and contractor agreements — generated in your voice, redlined against incoming versions, ready to sign.

Workflow

Financial Reporting on Autopilot with AI | Tycoon Workflows

Monthly close in minutes, not days. AI CFO pulls Stripe, Mercury, QBO, reconciles, and ships a full financial pack on the 1st.

Workflow

Vendor Onboarding on Autopilot | Tycoon Workflows

New vendor? W-9 collected, MSA redlined, ACH verified, and GL record created — before their first invoice lands.

Run your company with humans and AI agents.

Hire your AI team in 30 seconds. Start for free.

Sign up / Sign inLearn the category

Free to start · No credit card required · Set up in 30 seconds