Build a data room checklist tailored to round size and stage
intermediateClaude SonnetFounders & StartupFundraisingfundraisingdata-roomdiligenceseedoperations
Use case
Use this when you're prepping a fundraise. Founders waste enormous time either over-building a Series B-grade data room for a seed round or under-prepping and looking sloppy when an investor asks for the basics. This prompt produces a stage-appropriate checklist with priorities so you build what you need.
The prompt
You are a fundraising operator who has run dozens of rounds. You know the difference between what investors actually look at vs. what founders waste time on. Be ruthless. Round details: Round type and size:{{round_type}}(e.g., $2M seed, $8M Series A) Company stage:{{stage}}Industry / category:{{industry}}Lead investor profile:{{lead_profile}}(e.g., generalist seed, vertical specialist, strategic) How many investors do I expect to share the data room with:{{investor_count}}Specific things I know investors at this stage care about most for my category:{{category_specific_concerns}}Generate a data room checklist organized into: 1. **Tier 1: must-have before first investor meeting.** The minimum to not look unprepared. 2. **Tier 2: must-have before term sheet conversation.** What you need ready when an investor signals they're going to LP/partnership. 3. **Tier 3: must-have before close.** What confirmatory diligence will dig into. For each item: - What it is (specific document or data) - Why investors look at it (1 sentence) - Effort to produce (low / medium / high) - Common mistakes founders make on this item Then generate: - **What NOT to include** (5-7 items founders waste time on at this stage that nobody actually reads). - **The 3 documents that disproportionately matter** for this specific round size and category. - **A suggested folder structure** (so you don't dump 60 files in one folder). - **Access protocol recommendation** (how to share, watermarking, what to share before vs. after term sheet). Be specific to the inputs. A $2M seed checklist looks very different from an $8M Series A checklist; don't give generic advice.
Variables
{{{{round_type}}}}Replace with your {{round type}}{{{{stage}}}}Replace with your {{stage}}{{{{industry}}}}Replace with your {{industry}}{{{{lead_profile}}}}Replace with your {{lead profile}}{{{{investor_count}}}}Replace with your {{investor count}}{{{{category_specific_concerns}}}}Replace with your {{category specific concerns}}
Example
Input
round_type: $2M seed stage: pre-seed → seed, 8 months in, $32k MRR industry: vertical SaaS for mid-market apparel/logistics ops lead_profile: generalist seed funds with vertical SaaS portfolios; one strategic-adjacent angel investor_count: ~25-30 investor conversations expected, narrowing to 6-8 deep dives category_specific_concerns: - Net dollar retention and expansion data - ACV trend and discounting discipline - Sales cycle and CAC payback - SOC2 readiness (we don't have it)
Output
DATA ROOM CHECKLIST — $2M seed, vertical SaaS TIER 1: BEFORE FIRST INVESTOR MEETING 1. Pitch deck (final, dated, watermarked PDF) Why: investors share decks internally before the next meeting; make sure yours is the version you want them to share. Effort: medium. Mistake: sending a deck with a "DRAFT" watermark or a Google Slides link they can't share. 2. Two-page company summary (problem, wedge, traction, team, ask) Why: when a partner forwards your deal to others, they often forward this instead of the deck. Effort: low. Mistake: making this a deck-in-Word-doc form. It should read like a memo. 3. Top-line metrics dashboard (1 page) Why: investors want to see MRR, customers, NDR, burn, runway at a glance. Effort: low. Mistake: using vanity metrics (signups, page views) instead of revenue and retention. 4. Customer list with logo, ACV, start date, current ARR Why: investors will look at concentration, ACV trend, and recency. Effort: low. Mistake: anonymizing customers when you don't need to. Real names build credibility. 5. Cap table (clean, current) Why: "send your cap table" is one of the first 5 questions. Not having it ready signals disorganization. Effort: low (use Carta export). Mistake: stale cap table that doesn't reflect last advisor grant. TIER 2: BEFORE TERM SHEET CONVERSATION 6. Cohort retention analysis (logo and revenue retention by quarter) Why: NDR is the single most-scrutinized metric for vertical SaaS at seed. Lead with this. Effort: medium. Mistake: showing only logo retention; serious investors want both. 7. Sales pipeline (real, current, with stages and weighted forecast) Why: tells investors whether your traction is a fluke or a system. Effort: low (export from CRM). Mistake: showing a fake pipeline. Investors talk to your customers and detect inflation. 8. CAC payback and unit economics summary Why: at seed, investors don't expect mature unit economics, but they expect you to know yours. Effort: medium. Mistake: showing CAC payback without showing how you calculated it. Show the math. 9. Hiring plan tied to the round Why: confirms you've thought through what $2M actually does. Effort: low. Mistake: padding the plan. Investors discount aggressive hiring at seed. 10. Financial model (operating model + cash flow, 24 months) Why: not for the numbers — for the assumptions. Investors look at how you think. Effort: medium-high. Mistake: over-modeling. A simple spreadsheet with clearly named assumptions beats a 10-tab masterpiece. 11. Customer reference list (3-5, with permission to call) Why: lead investors will reference customers. Pre-warming them is your job, not theirs. Effort: medium. Mistake: not warming the references. Tell each customer who's calling and why. 12. Cofounder background and reference list Why: investors call backchannel references. Provide a list so you control the framing. Effort: low. Mistake: giving only friendly references. Investors will find people you didn't list anyway. TIER 3: BEFORE CLOSE 13. Customer contracts (sample MSA, ToS, sample executed contract) Why: legal diligence on contract structure. Effort: low. 14. Cap table with all underlying agreements (SAFEs, advisor grants) Why: confirmatory diligence. Effort: low. 15. Corporate documents (incorporation, bylaws, founder agreements, IP assignments) Why: legal diligence basics. Effort: low — but make sure IP is fully assigned. This is the most common founder mistake. 16. Bank statements (last 6 months) Why: confirms what you said about burn. Effort: low. 17. SOC2 status / security questionnaire response template Why: you flagged this as a concern. Even if you don't have SOC2, a written plan with timeline is what investors want to see. Effort: low to write the plan. WHAT NOT TO INCLUDE - Detailed competitor matrix. (Investors do their own; yours looks self-serving.) - Marketing materials, brochures, launch plans. - Detailed product roadmap (12+ months out). - Patent / IP strategy memos at seed. - Press hits older than 6 months. - "About us" / team values document. - Customer testimonial videos (if you wouldn't show your mom, don't include them). THE 3 DOCUMENTS THAT MATTER MOST FOR THIS ROUND 1. Cohort retention analysis (item 6). For vertical SaaS at seed, NDR is the single highest-signal metric. If yours is good, lead with it. If it's mixed, show it anyway and have the explanation ready. 2. Customer list with ACV trend (items 4 + 8). The Patagonia signing + 4 expansions in 60 days is your strongest narrative; the list lets investors verify it without asking you 3 more times. 3. SOC2 plan (item 17). You named compliance as a concern. A written plan with vendor and timeline turns "they don't have SOC2" into "they have a plan and are executing." That difference closes deals. SUGGESTED FOLDER STRUCTURE /00 Top of Funnel (Tier 1 only) /Deck (latest dated PDF) /Two-pager /Top metrics dashboard /01 Diligence /Customers (list, cohort, retention) /Financials (model, dashboard, bank summary) /Sales (pipeline, ACV trend) /Hiring plan /02 Confirmatory /Corporate (incorp, bylaws, cap table, agreements) /Customer contracts /Compliance (SOC2 plan) /References (customer + founder) /03 Misc (anything investor-specific) ACCESS PROTOCOL - Tier 1 only: open access via DocSend or watermarked PDFs. - Tier 2: gated — investor signs a simple NDA or you grant individual access. Watermarked. - Tier 3: shared after term sheet, individual access tracked. - For all stages: use DocSend or similar to track who's actually opening what. Investors who don't open the deck twice are not actually interested. Save your time accordingly.
Tips for best results
- 1Build the data room before you start meeting investors, not during. The 'I'll send that over' delays are momentum killers.
- 2Use DocSend or a similar tool to see who's actually engaging. Investors who 'love it' but never open the deck are passing politely.
- 3IP assignment is the single most common diligence trip-up. Make sure every cofounder, contractor, and early employee has signed an IP assignment before you start raising.
- 4If you don't have SOC2 (or any compliance), don't pretend it's not relevant. Have a one-pager: status, plan, vendor, timeline. That converts 'concern' into 'manageable risk' instantly.
- 5Don't over-watermark Tier 1 documents. Heavy watermarks signal paranoia and slow sharing. Watermark Tier 2+ where it actually matters.
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