Start Here: In One Sentence

• In one sentence, what do you need this round to accomplish for the company?
• What is your current target raise amount? Options: $5–10M, $10–20M, $20–30M, $30–40M, $40M+
• What is your current ARR range? Options: <$1M, $1–3M, $3–5M, $5–10M, $10M+
• How many months of runway do you have today (best estimate)? Options: <3 months, 3–6 months, 6–12 months, 12–18 months, 18+ months
• Who will be the primary owner/point-of-contact for this process on your side? Options: CEO / Founder, CRO / Head of Sales, CFO / Head of Finance, Head of People / Recruiting, Other

If Nothing Changes — The Cost of Status Quo

• If this round only preserves the status quo and doesn’t change your trajectory, what would that cost you in 12–18 months?
• Which operational constraint worries you most right now? Options: GTM hiring and quotas, Product roadmap delays, Customer churn/retention, Insufficient runway, Lack of finance systems, Other
• How long has that challenge been limiting growth? Options: <3 months, 3–6 months, 6–12 months, 12+ months
• Tell us about a recent moment when this constraint directly cost revenue or a strategic opportunity.
• What have you tried so far to mitigate this, and what stopped it from working?

One Metric to Prove This Round Worked

• Which single metric, if it meaningfully improved in 12 months, would prove this round succeeded?
• Select the top three KPIs that matter most to you for the next 12 months. Options: Annual Recurring Revenue (ARR), Net New ARR, Net Dollar Retention (NDR), Gross Churn Rate, Average Contract Value (ACV), Sales velocity / time-to-close, CAC payback period, LTV:CAC, Customer expansion rate
• What numeric target do you have for your primary KPI in 12 months (be specific)?
• Which short-term milestones would make you feel we're on track at 30 / 60 / 90 days?
• How do you prefer investor-facing progress to be measured and communicated? Options: Weekly dashboards, Monthly board pack, Quarterly review, Ad hoc updates

Who Holds the Keys — Decision & Cap Table Realities

• Who on your cap table or leadership team could realistically block or veto a plan if not aligned?
• Who will sign off on a final term sheet or close? Options: Founder / CEO, Board chair, CFO, Majority of founders, Other
• Are there cap table constraints or investor rights we should be aware of up front? Options: Pre-existing board commitments, Outstanding convertible notes, Required option pool top-up, Investor veto rights, No special constraints, Other
• Which investor or founder references would you expect from a lead before you commit? Options: Founder in same category/stage, Portfolio CEO who scaled sales, CFO/finance leader reference, Recruiting engagement reference, Other
• Describe the ideal board dynamic and governance cadence for the next 24 months.

If an Investor Is Going to Roll Up Their Sleeves

• What would operationally helpful investor involvement look like for you — beyond advice?
• Which platform services would move the needle most in months 1–12? Options: Executive recruiting (CRO/CFO), GTM playbook and sales hiring, Customer & partner introductions, Fractional finance / CFO support, Marketing & demand-gen resources, Board governance coaching
• Of those services, which three should be prioritized in the first 90 days? Options: Executive recruiting, GTM playbook, Customer introductions, Fractional finance, Marketing support, Board coaching
• How much hands-on board/investor involvement do you want versus strategic oversight? Options: Very hands-on (weekly/biweekly), Moderately hands-on (monthly), Strategic only (quarterly), Flexible depending on stage
• Give an example of the last time an external partner materially accelerated a hire, deal, or process — what made it effective?

Red Lines, Trade-Offs, and Deal Mechanics

• Which governance or economic term would be a deal breaker because it undermines your ability to execute?
• Which of these terms do you consider negotiable vs non-negotiable for this round? Options: Board seat for lead, Protective provisions / vetoes, Option pool expansion, Founder vesting adjustments, Liquidation preference multiple, Pro rata rights
• What is the minimum valuation or economic outcome that keeps your team motivated to accept a lead?
• Are there any legal, tax, or cap table issues we must resolve before closing? Options: Unallocated option pool, Outstanding founder disputes, Convertible note complexities, Investor consents required, No issues, Other
• Would you be willing to share a brief cap table snapshot to speed diligence? Options: Yes — ready now, Yes — with NDA, Not yet, Prefer later

Timing, Diligence, and Decision Mechanics

• If your ideal close slips by 3–6 months, what is the worst realistic outcome you’d face?
• What is your preferred close timeline? Options: Within 30 days, 30–60 days, 60–90 days, 90–180 days, 180+ days
• How flexible are you on trade-offs between round size and valuation? Options: Prefer larger size over valuation, Prefer valuation over size, Balanced / depends on terms, Undecided
• Which diligence items do you expect will be most time-consuming? Options: Financials / audit, Customer/reference calls, Cap table / legal, Product / security review, Operational readiness (HR/finance), Other
• Who on your team will own incoming diligence requests and investor coordination? Options: CEO, CFO / Head of Finance, Head of Legal, Founder, Other

Why Us — What Would Make Our Firm the Obvious Choice

• What would make our firm feel like the single best partner for this stage rather than just another interested investor?
• Which signals from a lead investor carry the most weight for you? Options: Relevant founder references, Proven GTM playbook, Track record of scaling ARR, Dedicated recruiting capability, Speed & clarity of process, Willingness for an active board seat
• Would you be willing to provide references for us to speak with (founder or customer)? Options: Yes — contact details ready, Yes — I will obtain permissions, Not yet / prefer later
• What would you like us to provide in the next 7 days to move this conversation forward? Options: Intro to lead partner, Sample term summary / term sheet outline, Diligence checklist, Intro to platform leads (talent/GTM/finance), Reference request form
• Any other concerns, context, or constraints we should know before preparing a term summary?

Quick Snapshot: Where You Really Stand Today

• How would you categorize your current ARR and growth rate in the last 12 months? Options: $1–3M ARR, $3–5M ARR, $5–10M ARR, >$10M ARR, Not tracking ARR yet
• Give a one-sentence summary of the revenue mix today (new logo vs expansion vs services).
• What percent of ARR comes from your top 5 customers? Options: <10%, 10–25%, 26–50%, 51–75%, >75%
• How consistent has monthly revenue been over the last 6 months? Options: Steady growth, Up and down but trending up, Flat, Declining, Highly volatile
• List the three KPIs you track weekly that matter most to hitting next quarter's revenue goal.

What's the Uncomfortable Truth About Your GTM?

• If you had to name one part of your go-to-market that is most likely masking poor scaleability, what is it? Options: Lead quality/volume, Conversion at demo stage, Contract negotiation/time to close, Pricing complexity, Post-sale expansion
• How long is your average sales cycle today for deals in your core segment (in days)? Options: <30, 30–60, 61–120, 121–240, >240, Varies widely by deal
• What is your current average ACV (annual contract value) and the typical buyer title? Options: <$25k, $25–75k, $75–250k, >$250k, Mixed across segments
• Where in the funnel do you see the biggest drop-off? Give a concrete example or metric.
• Which GTM motion is your primary focus today? Options: Inbound + SDR handoffs, Outbound enterprise AEs, Channel/partnership-led, Product-led growth, Hybrid

Which Customers Actually Pay the Bills (and Which Don’t)?

• Which customer segment produces your highest gross margin today—and why do you think that is?
• How do acquisition costs differ across your top 3 segments (choose best fit)? Options: Similar across segments, One segment much cheaper, One segment much more expensive, Unknown/not measured
• What is your net retention or NRR trend over the past 12 months? Options: >120%, 100–120%, 90–100%, <90%, Not tracking
• Tell us about the last 3 logos you won—what made them buy and how long did it take?
• Which buyer persona creates the most friction in closing deals (procurement, security, finance, operator, other)? Options: Procurement, Security/Compliance, Finance/Legal, Operator/End user, CEO/Exec sponsor, Other

Product Signals: Are Customers Using It the Way You Hoped?

• Which product usage metric keeps you up at night if you look at it honestly? Options: DAU/MAU, Feature adoption, Time-to-value, Trial->paid conversion, Churn within 90 days
• Share a recent customer story (positive or negative) that revealed a gap between expectation and reality.
• Which two features or capabilities are customers asking for most that you haven’t prioritized?
• How often do you measure active usage by cohort (weekly/monthly), and what patterns are emerging? Options: Weekly cohorts tracked, Monthly cohorts tracked, Occasional reviews, Not tracking cohorts
• Is time-to-onboard a predictable/controllable metric for you? If not, why? Options: Yes, predictable, Somewhat predictable, Unpredictable, We don’t track onboarding time

If One Hire Could Change Everything, Who Would It Be?

• Which open role, if filled with an exceptional person tomorrow, would have the biggest impact on revenue and why? Options: Head of Sales/CRO, VP/Head of Marketing, CFO/Head of Finance, Head of Customer Success, Senior Product/Engineering hire
• Where are your recruiting and hiring processes weakest—sourcing, interviewing, offer acceptance, ramp? Options: Sourcing, Interviewing/assessment, Comp packages/offers, Onboarding/ramp, We’re strong across the board
• How long does it take you to fully ramp a new revenue hire to quota (in months)? Options: <3 months, 3–6 months, 6–9 months, 9–12 months, >12 months
• What percent of current headcount are front-line revenue roles vs product/engineering vs ops/finance? Options: >50% revenue, 30–50% revenue, 10–30% revenue, <10% revenue
• What cultural or organizational barrier has derailed hires in the past?

Runway Realities: How Fragile Is Your Plan?

• If revenue fell 20% next quarter, what would be the first three line items you’d cut or delay?
• What is your current monthly burn and runway in months at today's burn? Options: <3 months, 3–6 months, 6–12 months, 12–18 months, >18 months
• What assumptions underlie your runway calculation (hiring pauses, churn rate, new deals)? List the top 3.
• How confident are you in your financial forecast for the next 12 months? Options: Very confident, Somewhat confident, Low confidence, No forecast yet
• When planning the next fundraise, which of these is the primary use of proceeds? Options: GTM expansion (sales & marketing), Product development/engineering, M&A/partnerships, Hiring senior leaders & ops, Extend runway

Channels & Partnerships: Are You Building Leverage or Hopes?

• Which revenue channel looks scalable but isn’t converting as expected? Options: Direct sales, Channel/partners, Marketplace, Inbound/organic, Product-led freemium
• Describe a partner or channel you invested in that failed to produce results—what went wrong?
• What percentage of pipeline today is partner-influenced or partner-sourced? Options: 0–10%, 11–25%, 26–50%, 51–75%, >75%
• What resources or incentives would make partners meaningfully more engaged? Options: Co-selling resources, Referral fees, Technical integration support, Joint marketing, Dedicated partner manager
• Are there regulatory, compliance, or procurement barriers in your target markets that partners help solve? Options: Yes - regulatory, Yes - procurement, No significant barriers, Unsure

Investor-Readiness: What Would a Board Member Immediately Fix?

• What is the single most glaring gap in your financial reporting or board pack today? Options: Lack of cadence/timeliness, Missing unit economics, No cash-flow scenarios, KPIs not aligned to strategy, We have a solid board pack
• How often do you produce board-level financials now and who prepares them? Options: Monthly, internal finance, Monthly, outsourced/VC-prep, Quarterly, Ad hoc, No formal board materials
• If an experienced investor joined your board today, what are the first three questions they would ask?
• Do you currently have a fractional/acting CFO or someone owning cash forecasting? Options: Full-time CFO, Fractional/acting CFO, Head of Finance (non-CFO), No finance leadership
• Which compliance or diligence items would slow a term-sheet process for you? Options: Cap table clarity, Employee contracts/equity, Revenue recognition/history, Customer contracts/auto-renewals, IP/technical documentation

If We Helped You One Thing Before Raising, What Should It Be?

• What single narrative or metric do you want investors to remember after meeting you?
• Which three milestones would most increase valuation or investor confidence in the next 6–9 months?
• How ready are you to provide referenceable founders/customparable customer conversations for investor diligence? Options: Ready today, Need to prepare list, Some references but not ideal, No references yet
• What type of platform support from an investor would move the needle most for you right now? Options: Executive recruiting, GTM playbook and hiring, Intro to strategic customers/partners, Finance/CFO recruiting and reporting, Board-level mentoring
• What is the earliest realistic fundraising timeline you can commit to if key gaps were closed? Options: Immediately (next 30 days), 1–2 months, 3–6 months, 6+ months, Unsure

Where the Company Really Is Right Now

• In one sentence, what's the single most important outcome you want this round to deliver for the company?
• How is ownership currently split among founders, employees (unvested + vested), and existing investors? (list key holders and approximate %)
• Do you currently have any outstanding SAFEs, convertible notes, or similar instruments that will convert at close? Options: Yes — SAFEs, Yes — Convertible notes, Yes — Other convertible instruments, No, Not sure
• What is the current option pool size as a percentage of fully diluted shares, and when (if ever) was it last refreshed? Options: <5%, 5–10%, 10–15%, >15%, Don't know / need cap table review
• Who on your team currently manages cap table changes, option grants, and shareholder communications? Options: Founder / CEO, Head of People / HR, Finance lead / Controller, Outside legal / law firm, Cap table platform admin, Other
• How many months of cash runway do you have today (assuming current burn), and how flexible is your hiring plan if the round timeline shifts? Options: <3 months, 3–6 months, 6–12 months, >12 months

If Your Cap Table Frays, Who Wins — and Who Loses?

• If we could be blunt: what would happen if the cap table needed to be materially restructured to close this deal? Options: Founder dilution increases, Existing investors dilute pro rata, Option pool expansion required, Round size reduced, Deal cannot proceed
• Which stakeholders must sign off on any cap table changes (e.g., major investors, founder majority, board), and how quickly can they provide approvals?
• Are there any anti‑dilution, ratchet, or protective provisions in prior documents that could materially affect post‑money ownership? Options: Yes — anti‑dilution, Yes — ratchets, Yes — protective covenants, No, Unsure — will need doc review
• Has there been any recent or planned secondary sale, transfer restriction waiver, or founder share repurchase that impacts available shares? Options: Yes — secondary planned, Yes — transfer waivers, Yes — repurchase planned, No, Unsure
• What would be the one cap table outcome you would refuse to accept, even if it meant the round stalled?

Option Pool: Are You Ready to Fight for Talent?

• If we expand the option pool at close, how much additional dilution are founders and existing holders prepared to absorb? Options: <3% additional, 3–7% additional, 7–12% additional, >12% additional, TBD / need scenario modeling
• Which roles are you planning to hire in the next 6–12 months that will require meaningful option grants? Options: Head of Sales / CRO, VP/Head of Marketing, Head of Customer Success, Finance / CFO, Head of People / Talent, Engineering leadership (CTO/VP Eng), Other
• Do you have current or planned mentoring/advisor agreements that include equity, and are those documented with vesting schedules? Options: Yes — documented with vesting, Yes — undocumented / verbal, No advisor equity, Unsure
• Would you prefer option pool expansion to happen pre‑money (increasing dilution to founders) or post‑money (reducing investor ownership)? Options: Pre‑money (founder dilution), Post‑money (investor absorbs), Open to either — want modeling, Undecided
• Tell us one hiring need you feel is most urgent and what failure to hire that role would cost the business in next 12 months.

Legal Diligence: What's Most Likely to Slow Us Down?

• Is there any intellectual property (IP) ownership that is unclear — e.g., contractor work without assignment, founder code contributed from prior employers, or disputed patents? Options: Clear — fully assigned, Minor items — contractor assignments pending, Significant risk — potential disputes, Unsure — need counsel review
• Do any material customer contracts include change-of-control clauses, assignment restrictions, or revenue‑based guarantees that could require consents? Options: Yes — change‑of‑control/consent required, Yes — assignment restrictions, No material restrictions, Unsure — need contract review
• Are there active or threatened legal claims, regulatory investigations, or tax audits we should surface now? Options: Yes — active litigation, Yes — regulatory inquiry, No, Unsure
• When was your last full corporate minute book and charter/bylaws review completed, and are all past board consents recorded? Options: Within 3 months, 3–12 months, >12 months, Never / unknown
• Who is your primary outside counsel, and are they comfortable supporting a fast diligence window (2–4 weeks)?
• What would be the single legal item you predict will require additional negotiation or delay?

Operational Access: Who Needs Logins, When, and Why?

• If an investor or platform teammate needs to start onboarding support on day one, which systems must they be able to access immediately? Options: Accounting system (NetSuite/QuickBooks), Cap table platform (Carta/Shareworks), CRM (Salesforce/HubSpot), G Suite / Office365, HRIS / payroll, Product analytics / data warehouse, Other
• Are there any security or compliance restrictions (SOC2, HIPAA, ISO) that limit what external partners can access? Options: SOC2, HIPAA, ISO, No restrictions, Unsure
• Who will be the designated operations contact to provision access and approve vendor onboarding (name, role, email)?
• Do you have centralized documentation for access credentials, admin accounts, and SSO configuration, or is access distributed across individuals? Options: Centralized — documented, Partially centralized, Distributed across individuals, No documentation
• Which of these onboarding tasks would you expect the investor / platform to lead versus support? (select all that apply) Options: Recruiting executive hires, Sales GTM design, CFO hiring & finance playbook, Customer intros & partnerships, Ops/Security hardening, Fundraising follow‑on support
• What internal approvals (legal, finance, board) will be required before we can grant external partners admin access?

Board & Governance Mechanics: Ready to Shift How Decisions Get Made?

• If we asked you to imagine the board one year from now, what would be the single most important governance change you’d want to see?
• What is the current board composition and are there existing reserved seats, observers, or standing committees?
• Do your current charter/bylaws include protective provisions (e.g., supermajority for key actions) that could affect ordinary course operations post‑investment? Options: Yes — multiple protective provisions, Yes — limited protections, No, Unsure
• How frequent would you expect board meetings and investor updates to be during the first 12 months after closing? Options: Monthly, Quarterly, Bi‑monthly / every 6 weeks, Ad hoc / as needed
• Are there any governance sensitivities (family shareholders, strategic investors, employee shareholders with special rights) that require a careful approach? Options: Yes — family/legacy shareholders, Yes — strategic investor constraints, Yes — unusual shareholder rights, No
• Who do you expect to nominate/accept the board seat from the lead investor, and are there preconditions to that acceptance?

Numbers That Can't Be Wrong: Financial Operations Readiness

• If an investor asked for a 12‑month rolling forecast and ARR build‑up today, how confident are you in delivering it within 5 business days? Options: Very confident, Somewhat confident, Need 1–2 weeks, Not confident
• What is your current month‑end close cadence and who owns it (internal finance, outsourced, interim CFO)? Options: Internal finance team, Outsourced / outsourced CFO, Interim finance leader, No formal close process
• Do you maintain customer‑level revenue recognition and ARR reporting (churn, expansion, new logo) in a system we can review? Options: Yes — detailed customer‑level reporting, Partially — aggregated only, No — manual or limited
• Are payroll, taxes, and benefits administered through a single provider that can supply records for diligence? Options: Yes — single provider, Multiple providers, Handled internally without provider, Unsure
• What financial governance items would you want the investor to help put in place first (select top two)? Options: Monthly operating review & KPIs, Board reporting pack template, Financial controls & approval matrix, Hiring a CFO/Head of Finance, ERP / accounting system upgrade
• Describe any irregularities or one‑off items (large credits, refunds, related‑party transactions) in the last 12 months that will need explanation.

If We Were Onboarding Tomorrow, What's Likely to Break First?

• What's the single biggest dependency — internal or external — that could derail a rapid onboarding after close?
• Which third‑party consents (major customers, lenders, landlords) are required to complete the transaction or to effect governance changes? Options: Customer consents, Lender/creditor consents, Landlord/lease consents, None, Unsure
• What is your ideal timeline from signed term sheet to platform onboarding kickoff, and what are non‑negotiable date constraints? Options: <2 weeks, 2–4 weeks, 4–8 weeks, >8 weeks
• Who are the three internal approvers whose buy‑in would speed decisions (name + role), and what will persuade each of them?
• If we encountered a gating issue, what contingency would you prefer: delay close, conditional board seat, or escrowed consideration? Options: Delay close, Conditional board seat / observer, Escrow / holdback, Other
• What immediate next step would make you feel most confident about execution after diligence — a single deliverable, meeting, or change?

Warm Up: Tell Us Where You Really Are

• In one sentence, how would you describe what your company does and who buys it?
• What is your current ARR (most recent trailing twelve months)? Options: <$1M, $1M–$3M, $3M–$5M, $5M–$10M, >$10M
• What was your year-over-year revenue growth (last 12 months)? Options: Declined, 0–25%, 25–50%, 50–100%, 100%+
• Which customer segment(s) drive the majority of ARR today? Options: SMB, Mid-market, Enterprise, Vertical-specific buyers, Marketplace/Platform, Other
• Describe your primary go-to-market motion in a sentence (e.g., inbound-led SDR motion, field sales, channel partnerships).
• How many months of runway do you have at current burn? Options: <3 months, 3–6 months, 6–12 months, 12–18 months, 18+ months

If We Took This Round and Stayed the Same — What Breaks?

• If you raised the target amount but didn’t materially change hiring or GTM strategy, what outcome would you expect in 12 months? Options: Better retention but slow growth, Faster growth with higher burn, No material change, Worse margins/instability, Other
• What is the single biggest constraint today that funding alone won’t fix?
• Which operational issue causes the most recurring friction right now? Options: Sales hiring & ramp, Product-market fit in new segment, Financial reporting/controls, Customer success/renewals, Technical debt/scale, Other
• How long has that issue been limiting progress (weeks, months, years)? Options: <3 months, 3–6 months, 6–12 months, 1–2 years, 2+ years
• Tell us about a recent deal, hire, or product decision that felt like a step forward — what made it work?

What Would Make This Round an Undeniable Win?

• If you look ahead 12 months, what specific metric shift would make you call this raise a success? Options: ARR target hit, Net revenue retention uplift, ACV growth, Sales efficiency (CAC payback), Profitability improvement, Other
• Please list the top three measurable milestones you need from this capital to feel confident (use numbers and timelines).
• Rank the following outcomes by importance for this round. Options: Growth acceleration (ARR), Unit economics improvement, Recruiting key leaders, Market expansion, Prepare for Series B/next raise, Governance/board partnership
• How will you measure investor value beyond capital? Name 2–3 concrete signals (e.g., 1:1 intros/week, help hire CRO in 90 days, board-driven GTM playbook).
• What timeframe would feel like a reasonable window to see the first meaningful signs of progress? Options: 30 days, 60–90 days, 3–6 months, 6–12 months

What an Ideal Lead Partner Does on Day One

• What would your ideal lead partner do in week one that would prove they move beyond cheerleading?
• Which types of hands-on platform support would you expect from a lead partner in the first 6 months? Options: CRO/Head of Sales recruiting, CFO/FP&A recruitment, GTM playbook & reps training, Intro to 10 target customers/partners, Operational playbook for ARR scaling, Other
• Tell us about a past investor interaction that genuinely changed your trajectory—what specifically did they do?
• Which board behavior would give you confidence: strategic challenge, operational help, or hands-off oversight? Choose one and explain why. Options: Strategic challenge, Operational help, Hands-off oversight
• What are three clear “no-go” behaviors from an investor that would make you regret taking money from them?

Who You Need to Hire (and How Fast) — the Talent Reality

• If you could hire only one senior leader in the next 90 days to change your trajectory, who would it be and why? Options: Head of Sales/CRO, VP/Head of Marketing, CFO/Head of Finance, Head of Customer Success, Product leader/CTO
• How long does it typically take you to hire a senior leader (end-to-end)? Options: <30 days, 30–60 days, 60–90 days, 90–180 days, 180+ days
• What’s the single biggest challenge you face when recruiting senior GTM or finance talent? Options: Candidate quality, Compensation constraints, Option pool limits, Cultural fit concerns, Competition from later-stage firms, Other
• How much additional option pool percentage (approx) would you be willing to create for critical hires this round? Options: 0%, 1–3%, 4–7%, 8–12%, Unsure/Need convo
• Describe one recent hire that didn’t meet expectations—what went wrong and what would you change next time?

Milestones, Dashboards, and the Proof You Can Show

• Which 3 KPIs do you currently update the board on every month? Options: ARR, Net Revenue Retention, New ARR (bookings), Gross Margin, Sales pipeline/velocity, Burn/Runway
• Which leading indicators do you rely on to predict revenue 3–6 months out? Options: Pipeline coverage, Average deal cycle time, Demo-to-close rate, Lead conversion rate, Sales rep ramp metrics
• How confident are you in your current financial operations (forecast accuracy, monthly close, cash tracking)? Options: Very confident, Somewhat confident, Not confident, We lack basic processes
• What reporting or dashboard would you want us to have access to as a board member in the first 90 days?
• What frequency and format for board updates would help you move faster (e.g., biweekly tactical, monthly KPI deck, quarterly strategy)? Options: Biweekly tactical, Monthly KPI deck, Quarterly strategy deep-dive, Ad-hoc as needed

Hard Trade-offs — What Are You Willing to Accept?

• If you had to accept one trade-off right now to secure the right lead investor, what would you accept (e.g., valuation below target, more governance, larger option pool)?
• Which governance structure would you prefer post-close? Options: Lead board seat + observer, Lead board seat + seat for co-investor, Independent board member along with lead, No change until next round
• Are there cap table or investor constraint issues we should know about (e.g., pro rata holders, late SAFE conversions, outstanding options)? Options: Yes — brief later, No
• What terms would cause you to pause or walk away even if the economics were attractive?
• How do you prefer to balance near-term growth vs. long-term durability when making hiring and pricing decisions? Options: Prioritize growth, Balance equally, Prioritize durability/stability

Who Must Be Convinced — The People, the Proof, the Timeline

• Who are the decision-makers and influencers we should engage in this process (titles and roles)?
• Which founder or investor references would you expect us to request before committing? Options: CEO of peer-stage portfolio company, CRO who worked with the firm, CFO reference, Limited partner reference, Other
• What materials would most accelerate internal approval (e.g., 12-month forecast, org chart, customer references, product roadmap)? Options: 12-month forecast, Hiring plan/org chart, Top customer references, Product roadmap + roadmap milestones, Data room access
• What is your preferred timeline for a decision on a lead investor (weeks to close)? Options: <2 weeks, 2–4 weeks, 4–8 weeks, 8+ weeks
• Are there board or investor conversations already scheduled that will influence timing (please describe)?

What Would Make You Say Yes Right Now?

• What is the single most convincing thing an investor could promise and deliver in the first 90 days?
• How would you prefer to pilot investor platform services initially — a short engagement (30–60 days) or a committed 6–12 month program? Options: 30–60 day pilot, 90-day sprint, 6–12 month partnership, Unsure — need guidance
• What operational access are you comfortable giving a lead investor during onboarding (e.g., dashboards, candidate interviews, customer lists)? Options: Full access to dashboards, Candidate interview access, Selective customer intros only, Limited financials until term sheet
• What are three immediate concerns we should address in the first call to make this discussion useful to you?
• Anything else we should know that would help shape a tailored plan for this round?