Due Diligence Data Room Skill

Build investor-ready and acquirer-ready data rooms for fundraising (SAFE, priced rounds, Series A/B) and M&A (sell-side or buy-side). This skill guides Sam Ledger through organizing DD documents, identifying gaps, scoring readiness, and producing a clean data room index.

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When to Use This Skill

Trigger phrases:

• - "Set up a data room"
• "What do investors need for due diligence?"
• "Prepare for Series A DD"
• "What documents do we need for the M&A process?"
• "Audit our data room"
• "Create a DD checklist"
• "We're getting acquired — what do they need?"
• "Rate our due diligence readiness"

NOT for:

• - Tax filing or accounting — use QBO/compliance workflows
• Smart contract security audits — use INLINECODE0
• Legal advice on specific clauses — refer to counsel
• Ongoing contract management — use INLINECODE1
• Cap table creation from scratch — use INLINECODE2
• Financial model building — use INLINECODE3

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Data Room Structure

Standard folder taxonomy used by institutional investors and M&A advisors:

CODEBLOCK0

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DD Readiness Scoring

Score each category 0–100 based on document completeness:

Category	Weight	Scoring Logic
Corporate	10%	All formation docs present, current, signed
Financial

25% | 3yr statements + monthly actuals + model + bank stmts |
| Cap Table | 20% | Fully diluted table + all agreements + 409A current |
| Commercial | 15% | Top 10 customer contracts + key vendor agreements |
| IP | 15% | Assignments from all founders/employees + IP inventory |
| HR/People | 10% | Employee list + exec agreements + benefits docs |
| Legal | 10% | Litigation disclosure + licenses + insurance |
| Technical | 5% | Architecture + security + SLA history |

Overall Readiness Score:

Score = Σ (Category Score × Category Weight)

Interpretation:
  90–100: Investor-ready. Proceed.
  75–89:  1–2 week gap closure. Flag gaps to founder.
  50–74:  2–4 weeks work. Significant gaps present.
  <50:    Not ready. Build foundational documents first.

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Gap Analysis Output

When auditing an existing data room, produce a gap report in this format:

CODEBLOCK2

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Document Checklist by Round Type

SAFE / Pre-Seed Round (Minimal DD)

CODEBLOCK3

Series A (Full Institutional DD)

All folders above, plus: CODEBLOCK4

M&A Sell-Side

All Series A above, plus:

□ 3 years tax returns (federal + state)
□ Historical financial statements (3–5 years)
□ All material contracts (customer, vendor, partnership)
□ Litigation history (last 5 years, including settled)
□ Environmental compliance (if applicable)
□ Real property leases
□ Insurance policies with coverage limits
□ Employee benefit plan documents (401k, health)
□ Change of control provisions in key contracts
□ Government contracts or regulated agreements

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Step-by-Step Workflow

Step 1: Scope the DD Type

Determine:

• - Type: Fundraising (which stage?) or M&A (sell-side or buy-side)?
• Timeline: When is the investor/acquirer expecting access?
• Audience: Who is reviewing? (VC, PE, strategic acquirer, family office?)

Step 2: Intake Audit

Ask the founder/CFO to share:

• - Existing data room link or folder structure
• List of what's been prepared vs. not started
• Any known legal issues (pending litigation, IP disputes)
• Outstanding cap table instruments (unconverted SAFEs, notes)

Step 3: Build Gap Report

Map what exists against the master checklist above. Score each category. Flag critical gaps (deal-stoppers) vs. nice-to-haves.

Step 4: Prioritize

Sequence by:

1. 1. Deal-stoppers first (IP assignments, 409A, audited financials)
2. Investor-specific asks (some VCs have custom checklists — get theirs)
3. Everything else in parallel

Step 5: Draft Document Summaries

For key documents, produce a 3-line summary:

• - What it is
• What it says (key terms)
• Any red flags or notes for investor

Step 6: Build the Data Room Index

Produce a master index document: CODEBLOCK6

Step 7: Final QA Pass

Before opening data room access:

• - [ ] All files named consistently (no "finalFINALv3.pdf")
• [ ] No personal employee info visible to all viewers (use sub-folders with tiered permissions)
• [ ] Sensitive items (bank statements, SSNs) restricted to appropriate viewers
• [ ] Index document is current and matches folder contents
• [ ] Watermarks on sensitive docs if required

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Example Interaction

User: "Our Series A investor wants data room access in 2 weeks. We've never set one up. Where do we start?"

Sam's response:

Two weeks is tight but doable if we move fast. Here's the triage plan:

FIRST 48 HOURS — Stop everything else, get these:

1. IP Assignments — every founder and early contractor must sign.
   This is the #1 deal-killer. I'll need: names of all founders,
   date company was incorporated, names of any early freelancers
   who touched the product.

2. Cap Table — send me whatever you have (spreadsheet, Carta export).
   I'll audit it and identify any missing countersignatures.

3. Financial Statements — do you have a CPA? If yes, request
   management-reviewed or compiled statements for 2023 + 2024.
   Full audit takes weeks — we'll flag the gap and provide reviewed.

THIS WEEK — Collect in parallel:
   □ All customer contracts (even just the signed MSAs/SOWs)
   □ Certificate of Incorporation + any amendments
   □ Board minutes (any major funding, equity, or officer decisions)
   □ Existing insurance policies (D&O is the critical one)

NEXT WEEK — Build + QA:
   □ I'll build the data room index and folder structure
   □ Financial model review and clean-up
   □ Full gap report for investor

What platform are you using for the data room? (Notion, Google Drive,
Carta Data Room, Caplinked, DocSend?) I'll tailor the structure.

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Platform-Specific Notes

Platform	Best For	Notes
Google Drive	Early-stage, SAFE rounds	Easy setup, permission by folder, familiar
Carta Data Room

Series A+ with Carta cap table | Native integration, investor-friendly |
| Notion | Small rounds, internal prep | Good for checklists, not ideal for investor DD |
| DocSend | Tracking investor engagement | Analytics on who views what, for hours |
| Caplinked / Intralinks | M&A, larger rounds | Watermarking, NDA-gating, enterprise features |
| Box / SharePoint | Acquirer-preferred in M&A | Enterprise IT often requires these |

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Red Flags to Surface to Counsel

When auditing documents, flag these immediately — do not attempt to resolve without legal:

CODEBLOCK8

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Integration Points

• - startup-financial-model — generate or audit the financial model included in Section 02
• cap-table-manager — build or reconcile the fully-diluted cap table for Section 03
• contract-review-agent — summarize and flag key customer/vendor contracts for Section 04
• kpi-alert-system — once funded, monitor key metrics investors will track post-close
• report-generator — format the gap report into an investor-ready PDF memo

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Reference: Series A Investor DD Checklist (Condensed)

CODEBLOCK9