Capital target and allocation

• Roughly what size check would you expect from a single growth investor on this round? Options: Below $100M (outside typical check size), 100M–249M, 250M–499M, 500M–999M, 1B+ (within typical range)
• Will proceeds be primarily for growth (primary), for secondary liquidity, or a material mix of both? Options: Primarily primary growth capital, Primarily secondary liquidity, Material mix of primary and secondary, Still determining

Timing and key milestones

• What is your target close window for this investment? Options: Within 30 days, 30–90 days, 3–6 months, 6+ months, No set timeline / exploratory
• What is the primary driver of that timing (one sentence)?

Decision-makers and approval path

• Who will ultimately sign or approve the investment? Options: Founder/CEO has signing authority, Board approval required, C-suite / finance committee signs, Existing lead investor consent required, Other
• Who else materially influences the decision (advisors, key board members, significant shareholders)? Options: Independent financial advisor / investment bank, Existing lead investor(s), Current board members, CFO / COO / other C-suite, Significant minority shareholders, Other

Confidentiality and advisor engagement

• Do you require an executed NDA before we review or share detailed diligence materials? Options: NDA already in place — materials can be shared, Yes — investor should execute an NDA, No — high-level materials are fine to start, Prefer to discuss confidentiality first
• Is a financial advisor or process agent managing the raise? If yes, please state their role and preferred contact (one sentence).

Opening the Conversation: Your Growth Story

• Tell me, how would you summarize your company's growth trajectory over the last 24 months? Options: Rapid (>=50% YoY), Strong (25-50% YoY), Moderate (5-25% YoY), Flat or negative (<5% or declining)
• Which revenue streams have driven most of that growth? Options: Existing product expansion, New product or feature launches, Geographic expansion, Large enterprise deals, Professional services or consutling, Other
• Describe the sales motion that produces your largest contracts, including average deal size and typical contract term.
• How long is a typical sales cycle for your top three customer segments? Options: <3 months, 3-6 months, 6-12 months, >12 months
• Walk me through a recent quarter where you beat or missed targets, what changed and why.

Where the Board and Cap Table Really Shift

• What single cap table or governance issue would make you pause or walk away from a new investor?
• Who currently holds control rights, protective provisions, or vetoes that would affect a minority investor's board seat?
• When was the last time the board amended governance documents, what changed, and why?
• Estimate the dilution impact, in percentage points, of your preferred financing scenarios over the next 12 months. Options: <5 pp, 5-10 pp, 10-20 pp, >20 pp, Not yet modeled
• Which existing shareholder groups are most likely to provide secondary liquidity, and what limits that possibility? Options: Founders, Employees through option exercise, Early institutional investors, Corporate investors, No obvious sellers, Other

The Growth Plan, the Missing Pieces, and Measurable Signals

• If accelerated international expansion is on the table, what operational gap would stop you from executing?
• What are the three milestones that would make you confident the company is IPO-ready within three years?
• Who owns each of those milestones today, and how do you measure progress against them?
• Describe your unit-economics model and name the single sensitivity that changes the outcome most.
• List the KPIs you report to the board monthly, and add any metrics you wish you had available. Options: ARR / Revenue, Gross margin, CAC and CAC payback, Net retention / churn, Bookings / new logo growth, Free response - add below

Who Decides, and How Fast

• What would make the founder or board accelerate a financing decision this quarter? Options: Clear primary growth use case, Urgent secondary liquidity need, Competitive bid driving faster timeline, Regulatory or contractual deadline, Other
• Name the internal decision-makers, advisors, and legal signatories needed to close.
• How compressed can your approval timeline get if diligence yields no surprises? Options: <2 weeks, 2-4 weeks, 4-8 weeks, >8 weeks
• When you run processes with advisors, what pace and deliverables have historically led to the best outcomes? Options: Rolling diligence with weekly syncs, Defined milestone gates every 2-3 weeks, Fast initial term sheet then detailed diligence, Other
• If the buyer proposed a term sheet consistent with your valuation targets, what internal hurdle would still prevent you from signing within four weeks?

What Keeps the Board Up at Night

• Identify the governance or operating risk most likely to trigger a board-level intervention this year. Options: Revenue shortfall, Key executive departure, Regulatory or compliance issue, Cash runway or liquidity event, Product failure or major customer loss, Other
• Tell me about a recent board disagreement, what were the stakes and how was it resolved?
• Name the single operational failure that would make you halt hiring, marketing spend, or expansion for a quarter.
• How do board reporting cadence and level of detail change when you are scaling versus when you are stabilizing? Options: More frequent with granular metrics, Same cadence, deeper narrative, Less frequent but with strategic updates only, Other
• If a potential investor demanded a board seat with veto rights over hiring or M&A, would you accept, negotiate, or walk away? Options: Accept, Negotiate limits, Decline / Walk away, Unsure

The Other Options You're Weighing

• What's the most persuasive alternative to taking external growth capital for you right now?
• Select which of the following alternatives you are actively evaluating. Options: Existing investor increases allocation, Strategic corporate investor, Debt or structured credit, Delay growth and fund from cash flow, Sponsor-to-sponsor secondary, Internal restructuring or cost takeout
• What would have to be true about your current approach for you to decide to stay with it instead of taking new capital?
• Has anyone on your team proposed funding the plan without an outside partner, and who would own that execution? Options: Yes, finance team, Yes, CEO and executive team, No, not proposed, Other
• If internal options could meet 80% of your growth plan in 12 months, would that stop you from raising now? Options: Yes, Probably, No, Depends on valuation and governance

Ready for Capital: Systems, Data, and People

• If we needed full access to monthly financials, unit-level revenue, and churn by next week, what would fail first?
• List the systems that hold your financials, customer records, and hiring data today.
• Identify the person who would manage integrations, and note how many dedicated engineering or data resources are available.
• Do you have APIs or export routines ready for extracts, and can they produce cohort and unit-level files we typically request? Options: Yes, fully available, Partially available, needs work, No, requires build
• Are there regulatory, compliance, or data residency restrictions that would extend diligence beyond 8 weeks? Options: Yes, likely, Possible, depends on scope, No
• If any of the answers above are no or limited, name the single constraint that would prevent us from completing diligence in 8 weeks.

Clear Next Steps and Deal Killers

• Under what circumstances would you sign a term sheet within seven days of receiving a draft? Options: Board pre-authorized terms, All major customers OK with plan, No material legal issues, Valuation and governance meet expectations, Other
• Provide the conditions or milestones that must be included in a term sheet for it to be acceptable to your board.
• Who needs final approval and what committee reviews would be required to close?
• How do you prefer to structure post-close operational support, standing board observer, dedicated operator partnership, or project-based engagements? Options: Standing board observer, Dedicated operator partnership, Project-based engagements, No post-close support wanted
• If the financing met your valuation and governance thresholds but could not offer secondary liquidity, would you proceed, postpone, or decline? Options: Proceed, Postpone until secondary available, Decline, Need to discuss with key shareholders

• Investment Partnership Experience

• Confirm the current state and its cost
• You confirm that at least one modeled capital and governance scenario meets your IPO-readiness timeline and dilution constraints.
• Seller to deliver a tailored capital-allocation scenario showing projected time-to-IPO and dilution under the proposed check size and alternate governance term sets.
• You confirm the proposed portfolio operations interventions close the top three capability gaps that were blocking IPO-readiness.
• Define the IPO-readiness target and milestones
• Seller to produce a one-page governance term comparison that maps rights to likely board composition and voting outcomes.
• You agree on the remaining evidence and decision criteria required before committing to the term sheet.
• Model capital allocation and governance scenarios
• Buyer to share the last three quarters of key operating metrics and a current cap table summary for scenario inputs.
• Buyer to prioritize the top three operational capability gaps they want portfolio ops to address for IPO-readiness.
• Walk through portfolio operations interventions
• Jointly identify up to three founder or board references for a short call to validate the seller's post-investment support model.
• Validate fit and remaining evidence

• Investment Partnership Experience
• Investment Partnership Deck
• Investment Partnership Brief

• meeting
• slides
• document

• Provide primary growth capital
• Fund secondary liquidity for shareholders
• Lead co-investor syndication and allocation
• Negotiate and execute investment closing
• Serve on the board and provide board counsel
• Embed a dedicated portfolio operations lead
• Execute go-to-market optimization program
• Implement margin improvement initiatives
• Recruit and onboard C-suite and VP hires
• Execute international expansion operations
• Execute dual-track exit process (IPO or sale)
• Manage sponsor-to-sponsor secondary transactions
• Deliver unit-economics underwriting model

Provide primary growth capital

• How much primary capital are you targeting for this round (select the band closest to your ask)? Options: ~$100M, $100M - $250M, $250M - $500M, $500M - $1B, >$1B
• Which tranche structure do you prefer for primary funding (tie to a use-of-proceeds milestone or single close)? Options: Single close, Tranche tied to growth milestones (specify milestones separately), Undrawn facility / delayed draw structure
• Which security type do you expect for the primary capital (reference prior-round instrument in your cap table schedule)? Options: Series preferred with stated liquidation preference, Convertible preferred or convertible note, Structured equity (custom governance/ratchet), Ordinary/common with warrant package
• Provide the high-level use-of-proceeds allocation that primary capital should fund (e.g., international expansion 40%, product R&D 25%, M&A 20%, working capital 15%).
• Which of the following documents will you make available in the data room to size primary capital (choose all that apply)? Options: Audited financial statements (last 2 years), Management three-statement model and cash runway, Prior-round purchase agreement and price per share, Customer contracts and revenue recognition policies, Other
• Who in your company will be authorized to finalize and sign term-sheet level agreements for the primary capital? Options: CEO, CFO, Board Chair / nominated director, General Counsel, Third-party financial advisor

Fund secondary liquidity for shareholders

• Which shareholder groups do you expect to include in secondary liquidity (reference your cap table schedule and shareholder ledger)? Options: Founders, Employees with vested options, Early investors / angels, Advisors
• What approximate dollar amount of secondary liquidity do you intend to support from the round proceeds or separate allocation? Options: No secondary requested, Up to $10M, $10M - $50M, $50M - $100M, >$100M
• Which operational artifacts will you provide to enable transfer of shares for secondary liquidity (choose all that apply)? Options: Shareholder transfer ledger / cap table export, Employee option grant files and vesting schedules, Tax withholding guidance from payroll provider, Share restriction / right of first refusal (ROFR) policy documents
• Are there existing contractual transfer restrictions or ROFR cycles that could delay secondary trades (e.g., investor purchase agreements, right-of-first-refusal timelines)? Options: Yes, No, Unsure - will verify with counsel
• How would you prefer proceeds for secondary liquidity to be delivered to sellers (wire to individual accounts, escrow then distribution, or transfer agent-managed)? Options: Direct wire to seller accounts, Escrow distribution post-closing, Transfer-agent facilitated re-issuance
• Who will coordinate beneficiary tax documentation and KYC for employees or founders participating in secondary sales? Options: Company payroll / finance team, External payroll / tax advisor, Company counsel, Individual sellers

Lead co-investor syndication and allocation

• Which allocation role do you expect the lead to take in syndication (sole lead, co-lead, anchor only)? Options: Sole lead / majority allocation, Co-lead with defined split, Anchor investor with limited allocation
• What minimum and maximum allocation ranges should co-investors expect to receive (express as percent of total round)? Options: <5%, 5% - 15%, 15% - 30%, >30%
• Describe any preferred co-investor categories or exclusions (for example: no direct competitors, only sector specialists, existing LPs of the lead).
• Which syndication artifacts will you supply for co-investor diligence (choose all that apply)? Options: Teaser / investor presentation, Data room access list, Management meeting schedule, Model package and cap table waterfall
• How quickly do you need syndication commitments after the lead term sheet (timing in calendar days)? Options: 7 days, 14 days, 30 days, 60+ days
• Who will manage investor onboarding, allocation tracking, and closing cap table updates? Options: Company CFO / finance team, Outside placement agent, Lead investor syndication desk, Transfer agent

Negotiate and execute investment closing

• Which closing timetable do you expect from signed term sheet to funds wired (answer in calendar days)? Options: 14 days, 30 days, 45 days, 60+ days
• Which closing deliverables will you provide or require in the data room (select all that apply)? Options: Board resolutions authorizing issuance, Updated certificate of incorporation / charter amendments, Signed purchase agreement drafts, Escrow instructions and wire details, Legal opinions
• Identify any regulatory or third-party consents required to close (for example: customer consent for assignment of material contracts, antitrust filings, CFIUS review).
• Which escrow or wire mechanism do you prefer for closing funds (select single option)? Options: Escrow agent with release conditions, Direct wire to company account on closing, Escrow to transfer agent then reissuance
• Who will be the primary legal contact to finalize the stock purchase agreement and ancillary documents? Options: Company counsel (GC or outside firm), Lead investor counsel, External deal counsel appointed by placement agent
• What evidence will validate closing completion (pick the set you require)? Options: Signed stock purchase agreement and board resolutions plus wire confirmation, Signed SPA, escrow release, and updated cap table on transfer-agent records, Signed SPA and transfer-agent share issuance record

Serve on the board and provide board counsel

• Which board composition are you seeking post-investment (number of seats and observer rights referenced to current board composition)? Options: One director seat, One director + observer, Two director seats, No director seat; observer only
• What governance rights are critical to you (reference investor rights agreement examples such as protective provisions, veto items)? Options: Protective provisions on major financings, Veto on change of control, Approval on hiring/compensation above threshold, None / standard rights
• Which committee participation do you expect the investor to take (audit, compensation, nominating)? Options: Audit committee, Compensation committee, Nomination & governance, No committee participation
• How often do you expect quarterly board materials to be delivered and what must they include (e.g., GAAP P&L vs. non-GAAP reconciliations, KPI dashboard)? Options: Monthly board pack with GAAP P&L and KPI dashboard, Quarterly board pack with full financials and KPI detailed review, Ad-hoc as requested
• Who will take primary responsibility for preparing the board packet and financial reconciliations? Options: Company finance team (CFO), Outsourced controller / accounting firm, Investor will prepare joint pack
• Are there charter amendments or investor rights templates we should review before proposing board mechanics? Options: Yes - will upload charter and investor rights agreement, No - clean charter, Unsure - will confirm with counsel

Embed a dedicated portfolio operations lead

• Which full-time equivalent (FTE) model do you prefer for the portfolio operations lead (fractional, dedicated on-site, or remote)? Options: Fractional (part-time engagement), Dedicated remote lead, Dedicated on-site lead
• What primary areas should the operations lead focus on in the first 90 days (select up to three)? Options: IPO readiness checklist, Sales go-to-market efficiency, Finance and reporting processes, Talent and recruiting pipeline, Margin improvement initiatives
• Which artifacts will you provide to enable a rapid ops ramp (choose all that apply)? Options: Access to CRM and revenue dashboard, Organizational chart and role descriptions, Current KPI dashboards and cohort analysis, Access to payroll and HRIS
• How do you prefer to measure the operations lead impact (example metrics: time-to-hire for VP roles, gross margin improvement points, forecast accuracy)?
• Who will be the primary internal sponsor for the operations lead (who will set priorities and enable cross-functional access)? Options: CEO, CFO, Head of Sales, Head of People / HR
• Are there any confidentiality or access constraints that would limit the operations lead (for example: no access to payroll, customer PII redaction)? Options: Full access permitted, Restricted access to specific folders, PII or regulated-data restrictions apply

Execute go-to-market optimization program

• Which GTM levers are highest priority for this program (select up to three: sales coverage model, pricing, channel expansion, customer success)? Options: Sales coverage and territory design, Pricing and packaging optimization, New channel partnerships, Customer success and expansion motions
• Provide the current ARR (annual recurring revenue) and three most important growth KPIs we should benchmark (e.g., net revenue retention, new logo ACV, average contract length).
• Which CRM and marketing automation platforms will the GTM program need to integrate with (list platform categories, e.g., source CRM, marketing automation)?
• How quickly do you expect initial GTM playbook pilots to launch (select timeline)? Options: 30 days, 60 days, 90 days, 120+ days
• Who will own validation of GTM program hypotheses and sign off on rollouts (role or team name)? Options: Head of Sales, Chief Revenue Officer (CRO), VP of Marketing, Product + Revenue committee
• Which sample artifacts should we review to design GTM experiments (choose all that apply)? Options: Current sales playbooks, Pricing lists and discount schedules, Top 10 customer contract samples, Customer segmentation matrix

Implement margin improvement initiatives

• Which margin levers are you open to pursue first (select up to three)? Options: Pricing optimization, Cost-of-goods-sold (COGS) reductions, Headcount and org redesign, Vendor renegotiation / procurement
• What current gross margin and EBITDA margin measure should we reconcile to in the initial analysis (provide the latest trailing twelve months GAAP metrics)?
• Which cost categories are off-limits for savings programs (for example customer-facing R&D that must be preserved)? Options: None - all categories open, Core R&D protected, Customer support headcount protected, Other
• Which systems hold the data needed to quantify margin opportunities (choose all that apply)? Options: ERP / finance system, Payroll and HCM, Procurement / AP system, Product usage analytics
• How should savings be measured and validated (examples: run-rate savings vs. one-time, GAAP impact vs. non-GAAP)? Options: Run-rate savings measured on GAAP P&L, One-time savings with implementation cost schedule, Non-GAAP operational improvement metrics
• What acceptance criteria will confirm margin initiative success (for example: X percentage points gross margin improvement sustained for two quarters)?

Recruit and onboard C-suite and VP hires

• Which executive roles are highest priority to fill (select all that apply)? Options: CFO, Chief Revenue Officer (CRO), Head of Product, VP Engineering, Chief People Officer
• What is the target timeline for each critical hire to be in role (30/60/90/120 days)? Options: 30 days, 60 days, 90 days, 120+ days
• Which sourcing channels should be used first for executive searches (choose all that apply)? Options: Existing investor network / references, Executive search firm retained, Internal referral pool, Market outreach via sector networks
• Which compensation structures are acceptable (select all that apply and note any fixed-term constraints)? Options: Base + equity package, Base + performance-based equity, Equity-heavy with lower base, Interim contract-to-hire
• Which onboarding artifacts will you provide for new executives (choose all that apply)? Options: 90-day plan expectations, Key customer and board briefing materials, Access to financial model and KPI dashboards, Org chart and role descriptions
• What acceptance criteria will confirm a successful executive hire (for example: signed employment agreement, background check cleared, start date and agreed 90-day deliverables)?

Execute international expansion operations

• Which target markets are highest priority for international expansion (list countries or regions and reference any existing local entities)?
• Which regulatory or tax artifacts must we review before launch (examples: local VAT registration, data residency rules, local employment law)?
• Which GTM model do you prefer abroad (direct local entity, distributor/partner, or marketplace channels)? Options: Local entity formation, Channel partners / distributors, Marketplace / aggregator channels, Hybrid model
• What is the expected initial budget for market entry and operating runway per market (provide estimate in USD)? Options: <$500k, $500k - $1.5M, $1.5M - $5M, >$5M
• Who will manage local compliance and payroll setup for new markets (internal HR, local counsel, international PEO)? Options: Internal People team, Local counsel, Professional Employer Organization (PEO), External payroll provider
• Which customer contract or data-transfer templates will be required for cross-border sales (e.g., DPA for data transfers, local master services agreement)?

• Executed Term Sheet
• Subscription / Stock Purchase Agreement
• Investors' Rights & Registration Rights Agreement
• Shareholders' / Voting Agreement
• Escrow and Holdback Agreement
• Conditions Precedent & Closing Checklist
• Disclosure Schedules and Disclosure Letter
• Side Letter for Secondary Liquidity
• Closing Mechanics & Wire Instructions
• Post-Closing Governance Transition Plan