Tell Me the One-Line Story We Can Share with Your Team

• How would you succinctly describe where the company is today—stage, momentum, and most recent growth signal? Options: Early scaling (25–50M revenue), Scaling (50–150M revenue), Mature growth (150–300M revenue), Other / prefer to write in
• Who are the founders and executive owners we should know, and what roles do they actively hold day-to-day?
• What single milestone in the last 12 months best demonstrates product-market fit or commercial traction?
• How would you describe the current operating team and headcount plan through the next 12 months? Options: Lean & founder-led, Growing with key managers, Scaled functions w/ established leadership, Hiring aggressively, Other
• Which sector best represents your core business today? Options: Enterprise software, FinTech / payments, Healthcare IT, SaaS-adjacent, Other

If Growth Had a Complaint, What Would It Say?

• What is the single biggest barrier keeping growth below your ambitions right now?
• How long has that barrier existed and what attempts have you made to address it? Options: <6 months, 6–12 months, 1–2 years, 2+ years
• Which of the following feels most like the choke point for scaling (pick up to two)? Options: Go-to-market efficiency, Pricing / packaging, Senior talent gaps, Product roadmap, Distribution partnerships, M&A capability
• Tell a short story about a recent moment when you felt growth was 'almost there'—what stopped you from pushing through?
• If an investor delivered the exact operational support you needed, what would be the first three changes you’d expect to see in 12 months?

What Keeps You Awake About Bringing in Outside Capital?

• What is your top fear about taking institutional capital for the first time? Options: Losing decision-making control, Being forced toward an exit timeline, Cultural mismatch with investors, Dilution of founder equity, Operational interference
• Which governance features are absolute non-negotiables for you? Options: Founder board control, Veto over sale/exit, Limited supermajority rights, No liquidation preferences, Defined hold period
• Has your team had prior experience with institutional investors? If yes, what felt good and what felt painful? Options: Yes - mostly positive, Yes - mixed, Yes - negative, No prior experience
• How would you describe the ideal board composition and meeting rhythm post-investment? Options: Founder-majority board, Investor/equal mix, Independent chair + founders, Advisory board instead of formal board
• What are the emotional trade-offs you’re worried about—what would you be willing to tolerate, and what would feel like a betrayal of the original mission?

Show Me the Capital Plan That Actually Moves the Needle

• What is the primary objective for new capital (select one)? Options: Accelerate GTM & sales, Scale product development, Platform M&A (tuck-ins), Executive hiring / bench, Balance sheet liquidity / debt paydown, Other
• What is your target capitalization ask—minimum acceptable and ideal check sizes? Options: $5–10M, $10–25M, $25–50M, $50–100M, >$100M / bespoke
• How do you feel about structures that preserve founder control but include preferred economic rights or board protections for investors? Options: Very open, Open with limits, Prefer straight minority common, Unsure / want to learn more
• Please allocate, in order, where the first tranche should be deployed (e.g., GTM, hires, M&A, product): Options: Go-to-market, Executive recruiting, M&A tuck-ins, Product & R&D, Systems & reporting, Other
• What runway (months) should the proposed capital provide, and how will you measure whether it’s sufficient? Options: 6 months, 9 months, 12 months, 18+ months

How Will We Know This Was the Right Move?

• What are the three metrics that, if improved, would convince you the partnership was justified? Options: ARR / Revenue growth, Gross margin expansion, Customer acquisition cost (CAC), Customer lifetime value (LTV), EBITDA / Cash flow, Employee retention
• What time horizon do you have in mind for meaningful outcome signals (select the single most important)? Options: 3 months, 6 months, 12 months, 24 months
• Which early milestones would allow you to renew enthusiasm for the partnership after close? Options: New VP hires onboarded, First tuck-in identified, Quarterly revenue beat, Pricing improvements implemented, Board governance established
• How do you prefer reporting and check-ins—structured dashboards, monthly tactical calls, or quarterly strategy reviews? Options: Structured dashboards + monthly calls, Monthly tactical calls only, Quarterly strategy reviews only, Ad-hoc as needed
• Tell us about a metric you’ve tried to improve but haven’t been able to—what got in the way?

Who Really Holds the Keys—Let’s Map the Decision Path

• Who must sign off on a minority capital event (list people and their roles)?
• Who are the advisors, attorneys, or board members that will influence final terms?
• What timeline constraints or windows of opportunity (e.g., customer seasonality, product launches) require us to move faster or slower? Options: Urgent - close in 30–45 days, Prefer 60-day close, Flexible 2–3 months, Need to wait for event (e.g., fiscal close)
• Are there internal approvals, shareholder consents, or option pools that could create surprises during diligence? Options: Yes - expect complexity, Somewhat - minor items, No - clean cap table, Unsure
• What would make your advisors say 'this is the right partner'—what evidence or terms convince them?

Would You Want to Speak to Someone Exactly Like You—What Would They Need to Hear?

• What type of founder reference would most reduce your risk (sector match, deal size, similar governance preference)? Options: Sector match + similar size, Similar governance outcome, Founder who retained control, Operator who used ops support, Other
• Which questions would you ask a reference to feel comfortable about cultural fit and hands-on support?
• How important is seeing a track record in your specific niche versus seeing broader category wins? Options: Specific niche is essential, Prefer niche but open to broader wins, Broader wins are fine
• Would you be willing to share three referees we can speak to, and what context should we give them? Options: Yes - three ready, Yes - but need time to prepare them, Prefer we speak to public references only, No
• What would a persuasive case study look like to you—what details must it include?

What Would It Take to Make a 60-Day Diligence-to-Close Real?

• If we agreed to target a 60-day close, what would be the single biggest internal obstacle to hitting that date?
• Is your data room in a state that would support a rapid close (financials, contracts, cap table)? Options: Fully ready, Mostly ready with a few gaps, Significant cleanup needed, Unsure
• Which diligence items concern you most and why (e.g., revenue recognition, customer concentration, legal contracts)? Options: Revenue recognition, Customer concentration, IP / product ownership, Employment agreements, Regulatory compliance
• Who on your team would be the day-to-day diligence contact and what is their bandwidth?
• What process change would make you most comfortable accelerating to close (e.g., staged closings, limited scopes, break fees)?

If We Closed Tomorrow, What Would You Want Us Doing on Day One?

• What's the single highest-impact priority you expect in the first 90 days post-close? Options: Prioritize hiring key execs, Launch GTM playbook, Begin integration of tuck-in targets, Implement financial reporting cadence, Other
• Who on your side will own each of the top three Day 1 priorities?
• What systems, access, or documents must be in place immediately for a smooth handoff to an operating partner?
• What risks in the first quarter could derail momentum and how would you expect us to help mitigate them?
• How would you prefer accountability to show up—weekly standups, KPI dashboards, or embedded ops support? Options: Weekly standups + dashboards, Embedded ops partner, Monthly review meetings, Ad-hoc support

Real Talk: Where Do You Stand on Moving Forward?

• Based on this conversation, how open are you to advancing to a term-sheet discussion in the next 30 days? Options: Ready to proceed, Interested but need prep, Not ready yet, Prefer to pause
• What would need to change between now and a term sheet for you to say yes?
• Who else do we need to meet and what would you like us to present to them? Options: Founder(s), Board / advisors, CFO / finance team, Legal counsel, Other
• What timeline works for a follow-up meeting to review a proposed structure or term sheet? Options: This week, Next week, In 2–4 weeks, Later / TBD
• Is there any additional context, documents, or constraints you want us to consider before we prepare next steps?

Quick Stage‑Setter: Who We’re Talking With

• Please confirm your name, title, and the legal name of the business we're discussing.
• What is your current annual revenue (most recent 12 months)? Options: <$25M, $25M–$50M, $50M–$100M, $100M–$300M, >$300M / prefer not to say
• Have you previously taken institutional capital? Options: No — bootstrapped or family-funded, Yes — seed/angel only, Yes — one institutional round, Yes — multiple institutional rounds, Prefer not to say
• Who will be involved in the decision to accept an investment (list names and roles)?
• Briefly, what is prompting exploration of outside capital right now (select all that apply and expand below)? Options: Scale GTM, M&A/tuck-ins, Product development/R&D, Geographic expansion, Liquidity/secondary, Talent hiring, Other

Do We Really See Your Market the Way You Do?

• When investors review your space, what do they usually get wrong about your customers or go‑to‑market? Tell us one example.
• How much of your business thesis depends on a market shift that’s not obvious to outsiders (e.g., pricing model change, regulatory tailwinds, revenge spending)? Options: Critical — the thesis hinges on it, Significant — an important driver, Some — a supporting factor, Minimal — not central
• Which of the following investor behaviors have felt dismissive or unhelpful in past conversations (select all that apply)? Options: Overemphasis on exit timing, Standardized governance templates, Surface-level market comparisons, Sales-focused, not product-focused, Short-term KPIs over compounding growth, None of the above
• If we wanted to understand one hidden dynamic in your market, what should we study first and why?

Who Tells the True Story? Founder References That Matter

• Which types of founder references matter most to you when evaluating an investor (pick top 3)? Options: Founder who kept control and scaled, Founder who exited in your sector, Founder who worked with operating partners, Founder who had a governance dispute, Founder who achieved fast organic growth, Founder who used capital for M&A
• Please provide 3–5 founder references most similar to your situation (include name, company, role, and best contact method).
• What specific questions would you want us to ask your references to validate fit and empathy (list 3)?
• Are there any references you prefer we not contact without prior warning? If so, why? Options: Yes — contact requires notice, Yes — please do not contact, No — feel free to contact directly
• Which reference outcomes would reassure you most that an investor understands founder governance (select up to 2)? Options: Founder retained board control, Investor added clear operating value, No pressure to exit early, Flexible hold period respected, Transparent, predictable reporting

When ‘Sector Expertise’ Is Real — Or Just Hype

• When investors claim sector expertise, what evidence convinces you that expertise is real rather than marketing?
• Which of the following operational supports would move the needle most for your company (rank your top 3)? Options: GTM playbooks & pricing, Executive recruiting, M&A/tuck‑in sourcing, FP&A and financial modeling, Customer success scaling, Regulatory strategy
• Can you name a competitor or peer where investor support materially accelerated growth? What did they actually do?
• How comfortable would you be if an investor's sector lead joined your board as an observer or advisor to accelerate execution? Options: Very comfortable, Somewhat comfortable, Neutral, Uncomfortable, Not at all comfortable
• What would you ask an investor to show you in the first 90 days to prove their sector value?

Governance: Where You’ll Compromise — and Where You Won’t

• If an investor suggested a governance change that would shift one decision area away from you, which single area would feel most threatening? Options: Board composition/control, Hiring/CEO replacement, M&A approval, Budget and capital allocation, Product direction, Other
• Select all governance terms you consider non‑negotiable for any minority investor. Options: Founder/CEO retains chair role, Founder-appointed majority of board, Veto rights limited to major dilution/merger, No forced exit timeline, No control for day-to-day ops, Supermajority for key decisions
• Describe a past governance term you accepted that later caused friction — what happened and how did it feel?
• What board cadence and reporting depth would preserve your autonomy while keeping investors informed? Options: Quarterly board with concise deck, Monthly updates + quarterly board, Ad hoc board calls as needed, Minimal reporting unless requested
• If we proposed protective provisions, which of these would you consider reasonable versus deal‑breaking? (choose all that feel reasonable) Options: Approval for related‑party transactions, Approval for new debt over threshold, Restrictions on large asset sales, Veto on changes to voting rights, Restrictions on dividends

How Long Should This Dance Last? Reframing Hold Periods and Exit Pressure

• Do you worry investors will push an exit before key strategic initiatives have matured — and if so, which initiative would you protect at all costs?
• What is your preferred minimum hold period for an investor in your business? Options: <2 years, 2–4 years, 4–7 years, 7–10 years, 10+ years / indefinite
• How flexible are you on hold period if the investor offers substantially more capital or strategic support? Options: Very flexible, Somewhat flexible, Prefer fixed hold, Not flexible at all
• Which exit paths are you open to now (select all that apply)? Options: Strategic M&A, IPO, Secondary sale to another institution, Maintain long-term private ownership, Minority sale combined with recap
• How would you like exit alignment documented early in the process to avoid misunderstandings later? Options: Clear hold-period clause, Exit governance matrix, Regular exit strategy reviews, No formal documentation until term sheet

If We Call Your References — What Will They Tell Us?

• What uncomfortable truth about your company are you most worried a reference might reveal?
• Which reference is most likely to speak candidly about governance tensions and why?
• What are the top five questions you want us to ask your references to validate cultural fit and governance sensitivity?
• Best time and method to contact your references? Options: Email — daytime, Phone — daytime, Email — evening, Phone — evening, Other
• Do you give us permission to contact these references directly, and are there any specific frame/context you want us to use when reaching out? Options: Yes — contact directly, Yes — contact after we notify you, No — do not contact yet

Fit Signals — How We’ll Know This Is the Right Partnership

• Imagine six months after investment you feel optimistic — what three tangible changes would prove the partnership is working?
• Which early KPIs should we set together to surface alignment quickly (pick up to 4)? Options: ARR growth rate, Net retention, Gross margin improvement, Customer acquisition cost reduction, Key hire completion, Number of tuck‑in opportunities reviewed
• How would you like disagreements to be handled in the first year — rapid escalation to founders, mediator, or scheduled governance review? Options: Direct founder-to-founder conversation, Structured mediation, Quarterly governance reviews, Investor-led recommendations with founder veto
• What would constitute an early red flag for you that the investor isn’t the right fit?
• Which forms of investor support would you value most in onboarding (select up to 3)? Options: Dedicated operating partner, GTM diagnostic & 90-day plan, Executive search support, M&A pipeline introductions, FP&A and reporting setup

What Would Speed Comfortable Validation for You?

• If we could do one thing in the next 48 hours to make you more comfortable moving forward, what would it be?
• How complete is your data room and which materials would expedite our validation (select all that apply)? Options: Financials & models, Cap table and option plan, Customer cohort analysis, Org chart & key hire briefs, Contracts and legal docs, Product roadmap
• Ideal timeline for diligence-to-term-sheet from your perspective? Options: <30 days, 30–60 days, 60–90 days, Flexible/depends on scope
• Who on your team should be the primary point of contact for reference coordination and diligence logistics?
• Anything else we should know now that would make our reference and fit validation more honest and productive?

Quick Company Snapshot — Help Us See You

• In one sentence, how would you describe your company, the problem you solve, and your ideal customer?
• What is your current trailing twelve‑month revenue (T12)? Options: <$25M, $25M–$50M, $50M–$100M, $100M–$300M, >$300M
• How would you characterize your revenue growth over the past 12 months? Options: Declining, Flat, 5–15% CAGR, 15–40% CAGR, >40% CAGR
• Who are the primary decision‑makers we should expect to engage with during diligence and negotiation? Options: Founder‑CEO, Co‑founder/CXO, CFO/Head of Finance, Trusted external advisor/attorney, Existing board member, Other
• Briefly summarize your current ownership and capital structure (majority founder, outside investors, material debt, etc.).

If You Don’t Raise — What Keeps You Up at Night?

• What is the single most consequential outcome for the business in 12–24 months if you don’t secure the right capital partner?
• Which part of the business would suffer first without new capital? Options: GTM/Revenue scaling, Product R&D/roadmap, Key hires/talent retention, M&A/opportunistic deals, Working capital/operations, Other
• How long can you execute your current plan on existing resources (months)? Options: <3 months, 3–6 months, 6–12 months, 12–24 months, >24 months
• When you picture failing to take the next step, what emotions or pressures show up for you and the team?
• Give a recent example where limited capital prevented you from pursuing a clear opportunity—what happened and what was the impact?

What’s the One Constraint Slowing Your Next Leap?

• If you could fix one internal constraint tomorrow that would accelerate growth most, what would it be?
• How predictable and unit‑economics‑driven is your business today? Options: Highly predictable and repeatable, Somewhat predictable, Emerging but volatile, Unclear / need better visibility
• Where do you see the most revenue or margin leakage today? Options: Pricing & packaging, Customer churn/retention, Sales efficiency / CAC, Onboarding & activation, COGS/service delivery, Other
• Describe your current sales motion (average deal size, typical sales cycle length, primary channels).
• Have you run recent pricing, packaging, or GTM experiments that materially moved metrics? What changed and what were the results?
• What revenue milestone are you aiming for next, and what is your preferred timeline to reach it? Options: 6 months, 12 months, 18 months, 24 months, Longer / other

What Must Never Change — Your Non‑Negotiables

• If an investor asked you to change one element of governance or control, what would cause you to walk away?
• Which governance or control rights are absolute non‑negotiables for you? Options: Founder board control/lead chair, Veto on strategic sale, No forced exit timeline, Retention of day‑to‑day operational authority, Limited dilution protections, Other
• How comfortable are you with introducing institutional reporting, quarterly forecasts, and an investor review cadence? Options: Very comfortable, Somewhat comfortable, Prefer limited reporting, Worried about losing autonomy
• Who on your side must sign off on governance changes (names/roles)?
• Tell us about a past investor relationship that felt misaligned—what specifically went wrong and how did it affect the business?

Capital — Intent, Structure, and the Real Use of Proceeds

• Beyond the headline amount, what outcomes must this capital enable for you to consider the partnership a success?
• What is your target raise size or valuation range for this round? Options: <$10M, $10M–$25M, $25M–$50M, $50M–$100M, >$100M
• Do you intend to use proceeds for primary growth, secondary liquidity, debt paydown, M&A, or a mix? Please indicate expected allocation percentages or priorities.
• Are you seeking primary capital, secondary liquidity for founders, or a combination? Options: Primary (growth) only, Secondary (liquidity) only, Combination of both, Undecided
• What maximum ownership dilution are you willing to accept to achieve your goals? Options: <5%, 5–10%, 10–20%, 20–33%, >33%
• What is your ideal closing timeline to meet business needs? Options: <30 days, 30–60 days, 60–90 days, 90–180 days, Flexible

Talent & Operating Gaps — Who Will Make the Plan Real?

• If hiring one role would unlock 30% more growth tomorrow, which role is it and why?
• Which functions are currently the hardest to recruit or retain? Options: Sales leadership, Head of Marketing/Rev Ops, Product leadership, Engineering/CTO level, Finance / FP&A, Customer success, Other
• Have you used external operating partners, fractional executives, or the firm’s recruiting network before? What worked and what didn’t?
• How quickly can you onboard a strategic hire if the right candidate is presented? Options: <30 days, 30–60 days, 60–90 days, >90 days
• Would access to an operating playbook and active recruiting support materially change your timeline to hit milestones? Options: Dramatically, Somewhat, Not much, Unsure

Growth Through M&A — Is Inorganic Speed an Option?

• Would pursuing tuck‑ins or targeted acquisitions accelerate your plan more effectively than organic investment—and if so, why hasn’t it happened yet?
• Have you completed acquisitions before? Options: Yes, multiple times, Yes, once, No, but considered, No, never
• Which kinds of targets make the most strategic sense for you? Options: Smaller competitor / customer consolidation, Adjacency product, Talent/engineering shop, Customer base expansion, Proprietary tech/IP, Other
• What maximum acquisition size (by revenue) could you realistically integrate right now? Options: <$2M, $2M–$10M, $10M–$25M, $25M–$50M, >$50M
• How much of integration could your team handle internally versus needing hands‑on partner support? Options: Fully in‑house, Mostly in‑house with partner support, Prefer partner‑led integration, Unsure

Success Signals — The First 90 Days and How We’ll Know

• If at t+90 days you had to be honest, what would make you say ‘that investment was worth it’?
• Which top‑three KPIs will prove impact in the first 90 days? Options: Net new ARR / revenue, Sales pipeline velocity, Gross margin improvement, Customer retention / churn, Key hires onboarded, M&A pipeline created, Operational cost reduction, Product adoption / engagement
• What reporting cadence and format do you want post‑close to keep things moving (select preferred)? Options: Weekly operational check‑ins, Bi‑weekly, Monthly, Quarterly business reviews, Ad hoc updates
• Who on your side must approve the 90‑day plan and be accountable for execution? Options: Founder‑CEO, Executive team, Board/advisors, Lead investor, Other
• What warning signs would make you raise the alarm that we need to change course?
• Are you willing to commit to an aligned 90‑day plan with clear owners and measurable milestones? Options: Yes, Maybe with conditions, Not ready

Decision Rhythm — Who Signs and How Quickly?

• If a term sheet arrived today on your ideal terms, what would stop you from signing it?
• List the people who must be involved in the final decision and their roles (name/role/email if possible).
• Who will lead negotiations on your side (CEO, external counsel, board rep, CFO, other)? Options: Founder‑CEO, External counsel, Board member, CFO/finance lead, Other
• What decision timeline are you targeting from initial term sheet to signed agreement? Options: Immediate (<2 weeks), 2–4 weeks, 4–8 weeks, 8+ weeks, Undecided
• Which diligence items typically take longest for you to assemble and why?

Start Here — Tell Us Who You Are

• In one crisp sentence, how do you describe what your company does and the core customer problem you solve?
• Which revenue band best describes your company today? Options: $25M–$50M, $50M–$100M, $100M–$200M, $200M–$300M, Prefer not to say / other
• Which vertical best fits your business? (select up to two) Options: Enterprise Software, Fintech / Payments, Healthcare IT, SaaS/Cloud infra, Vertical SaaS (other), Other
• How long have you been scaling with institutional intent (i.e., thinking about outside capital)? Options: Under 6 months, 6–18 months, 1–3 years, 3+ years, Never formally considered it
• Who makes day-to-day operating decisions and who is the ultimate decision-maker for strategic capital choices?
• What’s one recent win that tells us you’ve passed product-market fit?

Who Actually Moves the Needle?

• If this investment required a fast yes, who in your circle would give it—and who would slow it down?
• Please identify all people who must sign off (title + role) and how they like to be involved during deals.
• Which trusted advisors (attorneys, board members, mentors) will influence the decision and how do they typically assess investors? Options: Founder counsel / attorney, External board member(s), CFO / financial advisor, M&A advisor, No advisor involved, Other
• What timeline constraints are non-negotiable for your team (e.g., fiscal year, product launches, fundraising blackout periods)? Options: Need close within 60 days, Close in 3–6 months, Prefer flexible timing, Tied to product / revenue milestone, Other
• What governance preferences would you describe as absolute deal-breakers (e.g., board majority, veto over hiring, liquidation preferences)?
• Thinking emotionally, who on your team would be most anxious about outside capital and why?

Are Investors Missing What Matters to You?

• What do investors typically misunderstand about your customers, market pace, or growth levers?
• Have you had prior investor conversations where their assumptions felt off? Tell us one specific example and the consequence.
• Which sector-specific hurdles keep you up at night (pick all that apply)? Options: Complex procurement cycles, Regulatory constraints, Long sales cycles / enterprise adoption, Payment / billing complexity, Talent scarcity, Other
• How worried are you about losing decision-making authority once you accept institutional capital? Options: Very worried, Somewhat worried, Neutral, Not worried
• If an investor truly ‘gets’ your market, what would they say differently in the first 10 minutes of a meeting?
• What emotional signals or behaviors from an investor would make you relax and say, 'They understand us'?

Reference & Track Record: Which Signals Matter Most?

• If we asked three founders you respect whether an investor is founder-friendly, what evidence would convince you they’re being honest?
• Please list comparable founder references (company, founder, year of investment) you’d be comfortable us speaking with.
• What outcomes from past investor partnerships matter most to you (select up to three)? Options: Go-to-market acceleration, Executive recruiting, Tuck-in M&A support, Financial planning / FP&A, No interference in daily ops, Other
• What’s an acceptable hold period in your view for a minority growth investor? Options: 3–5 years, 5–7 years, 7–10 years, No strong view
• What governance arrangements from past deals felt respectful of founders—and which didn’t?
• Would you be willing to share a past investor reference who can speak to both upside support and hard lessons? If so, who? Options: Yes — provide contact, Yes — internal reference only, No

What Would 24 Months of True Progress Look Like?

• If everything went right for the next two years, what would be the single most visible change to customers or employees?
• Which metrics would you use to prove that growth equity was the right move (select up to three)? Options: ARR / Revenue growth rate, Gross margin improvement, Net retention / upsell rate, Customer acquisition efficiency (CAC payback), EBITDA expansion, Other
• What market opportunities do you feel are within reach only if you had the right partner/capital?
• Which of these outcomes would you prioritize if you could only pick two? Options: Faster product development, Nationwide / international expansion, Significant hiring in sales/CS, Strategic tuck-in acquisitions, Improved unit economics, Other
• How would hitting those outcomes change your personal and professional life? Be specific.
• What would you be unwilling to sacrifice in pursuit of aggressive growth?

Use of Capital — Where It Has to Move the Needle

• If you had to spend this round of capital on one initiative even at the expense of others, what would that be?
• Which allocation split best represents your current thinking for new capital? Options: >50% go-to-market / sales, >50% product / R&D, Balanced GTM + product, M&A-first (tuck-ins), Primarily working capital / balance sheet
• How many senior hires do you expect to make in the next 12 months and in which functions? Options: 0–1, 2–4, 5–10, 10+
• Are you actively looking at acquisitions? If so, what size and strategic fit do you prefer? Options: No, Yes — small tuck-ins (<$5M), Yes — mid-sized ($5M–$25M), Yes — strategic larger targets
• What performance improvements (e.g., CAC payback, churn reduction) do you expect capital to deliver within 12 months?
• What reporting or governance milestones would make you comfortable releasing capital in stages?

Control and Governance — Where You Draw the Line

• What’s one decision you would never want an investor to have a vote over—and why does it matter?
• Which board composition feels right to you after a minority investment? Options: Founder retains board majority, Founder retains board chair but equal seats, Independent chair with founder influence, Investor-desired seat(s) only, Other
• What protective provisions do you consider reasonable versus deal-breaking (examples: liquidation preference, anti-dilution, drag/tag rights)?
• How frequently do you want investor-facing reporting and in what form? Options: Weekly operational dashboards, Monthly KPIs and commentary, Quarterly board packs, Ad-hoc as requested, Other
• What governance language or past clause have you found confusing or harmful in prior term sheets?
• If a governance compromise were required to accelerate close, which concessions would you consider and which would remain off-limits?

Diligence & Timing — Can We Close in 60 Days?

• If a 60-day close is possible, what’s the single item most likely to derail that timeline?
• How complete is your current data room across these areas (financials, contracts, cap table, IP, customer lists)? Options: Comprehensive and ready, Mostly ready — a few gaps, Significant gaps, No formal data room yet
• Who would own the diligence process on your side (name and role), and how many hours per week can they commit?
• Do you have any external audits, compliance certifications, or pending legal matters we should know about? Options: Yes — provide details, No, Prefer to discuss privately
• Which closing condition would you consider a non-starter (e.g., escrow size, earnout, restrictive covenants)?
• What does an ideal 60-day diligence-to-close plan look like from your perspective?

First 90 Days — What Will Make Deployment Work?

• If the first quarter after close fails, what single preventable cause would you point to?
• What are the top three milestones you expect to hit in Q1 post-close?
• Which operational owners will be accountable for those milestones (name + role)?
• What reporting flows should we establish immediately (select all that apply)? Options: Weekly GTM dashboard, Monthly financials with variance analysis, Quarterly strategic review, People / hiring updates, M&A pipeline updates, Other
• What onboarding support would be most valuable from an operating partner (select up to two)? Options: Go-to-market playbook execution, Executive recruiting / talent mapping, M&A sourcing & diligence, FP&A and cash management, Sales compensation design, Other
• How would you prefer to handle post-close issue escalation if priorities diverge? Options: Weekly leadership sync, Designated escalation owner + SLAs, Ad-hoc executive conversation, Board-level intervention only

Signals of Success — How We’ll Know We Did Right

• When you look back at this partnership in 18 months, what three signals will tell you it was the right move?
• Which quantitative targets would you lock in as success signals (choose up to three)? Options: Revenue CAGR, Net retention rate, Gross margin, EBITDA margin, Customer acquisition cost payback, Other
• What qualitative signals matter—culture preservation, founder autonomy, or access to certain networks? Options: Culture preservation, Founder retains decision rights, Access to GTM / customer network, Improved recruiting / talent pool, Other
• How would you like to maintain a shared channel for issues and enhancements after close? Options: Slack channel with investor team, Monthly joint review, Quarterly board + operating partner, Dedicated portal / dashboard
• What would make you recommend this investor to another founder—what’s the single most important experience or behavior?
• Any final concerns or ‘soft signals’ we should be aware of before moving ahead?