Start Here: Your One‑Sentence Story

• In one sentence, how do you describe the company and the core opportunity we should understand right away?
• Which revenue band best describes your last 12 months of ARR / revenue? Options: $50M–$100M, $100M–$200M, $200M–$350M, $350M–$500M, >$500M
• What round are you raising now, and roughly how much capital are you targeting? Options: Series D, Series E, Growth/Expansion (post‑Series E), Other
• How would you summarize, in plain terms, the three primary uses of proceeds you expect for this raise?
• Who is owning the process on your side—founder, CEO, CFO, banker, or another advisor? (select all that apply) Options: Founder/CEO, CFO/Finance Lead, Board Chair/Board Member, Investment Bank/Placement Agent, Legal Counsel, Other

What’s Actually At Stake?

• If this round doesn’t land when planned, what will be the single biggest negative consequence for the business?
• Which of these describes the primary objective for this raise? Options: Accelerate go‑to‑market and growth (primary capital), Fund M&A or inorganic growth, Provide secondary liquidity to employees/early investors, Extend runway while optimizing margins, Other
• How important is limiting dilution versus maximizing valuation—choose the priority that reflects your board/founder preference? Options: Minimize dilution first, Maximize valuation first, Balance both equally, Depends on investor terms
• Quantitatively, what dilution range would feel acceptable to you for this round? (give a percent or range)
• How would you describe the board’s appetite for giving up governance (board seats, veto rights) in exchange for a higher valuation or strategic partner? Options: Comfortable with one or more new board seats, Prefer observers only, Very conservative—limited governance changes, Open depending on investor

Who Holds the Keys — Board, Advisors, and Hidden Vetoes

• When the board has to say yes, what’s the most common reason a deal gets slowed or blocked?
• What is your current board composition and voting threshold for approving a financing? Options: Founder + independent majority, Founder holds special voting rights, Investor majority, Board requires supermajority, Other
• Which outside advisors materially influence decisions on financing terms (select all that apply)? Options: Investment bank, PE/growth investor advisor, Legal counsel, Big‑4/accounting advisor, Family office/advisor, Other
• Tell us about a past board conversation on capital that changed the course of the company—what happened and why did it matter?
• Who, beyond the board, must sign off on the final documents (e.g., major shareholders, founders, lenders)?

Money, Mechanics, and Control — Hard Terms, Soft Consequences

• What governance or control provisions would be an absolute deal breaker for you?
• Do you have a firm preference for the investor taking a board seat, an observer role, or no formal governance role? Options: Board seat required, Observer preferred, No governance role desired, Flexible depending on investor
• What types of covenants (financial covenants, information rights, restricted actions) are you prepared to accept, and which feel excessive?
• For the split between primary and secondary proceeds, what allocation feels right to you? Options: Primarily primary capital (>80% primary), Balanced (50/50), Primarily secondary (>80% secondary), No secondary planned
• How important is it that co‑investors be aligned on follow‑on reserve and exit strategy? Options: Critical, Important, Nice to have, Not important

Valuation, Dilution, and the Emotional Ledger

• What valuation range would signal to you that an investor truly understands and respects the company’s trajectory?
• How tied are your valuation expectations to the prior round price and protections granted to earlier investors? Options: Very tied, Somewhat tied, Not tied—market sets price, Unclear
• How do you expect to handle employee equity communications if there’s meaningful dilution or a secondary component? Options: Proactive townhalls and written comms, Advisory sessions for key hires only, Minimal communication, Other
• Are there anti‑dilution or ratchet protections you cannot accept? Tell us which and why.
• What would a realistic post‑money cap table look like (ownership % ranges for founders, employees, new investor)?

Timeline & Speed: Tradeoffs Between Momentum and Terms

• If you had to choose: would you rather close faster at slightly worse economics, or take more time to negotiate materially better terms? Options: Close fast, Take time for better terms, Depends on market and investor
• What is your target close date and what internal milestones must be met before then? Options: <30 days, 30–60 days, 60–90 days, 90+ days
• How ready is your diligence package—cap table, audited financials, customer metrics, legal docs? Options: Fully ready, Mostly ready with some gaps, Not ready—work to do, We’ll need help preparing
• What timeline risks keep you up at night (e.g., board availability, regulatory approvals, audit timing)?
• Would you consider an exclusivity window if it meaningfully shortens the path to a signed term sheet? Options: Yes, comfortable, Maybe—depends on length, No

Secondary Liquidity — Who Gets Cash and Why?

• How important is it to provide liquidity to early employees or founders in this round? Options: Very important, Somewhat important, Not important, Prefer to keep primary only
• If offering secondary, which groups should be prioritized (select all that apply)? Options: Early employees, Founders, Seed/early investors, Key hires, Other
• Do you anticipate tax, consent, or ROFR/ROFO constraints that could complicate secondaries? Options: Yes, several, A few minor issues, No major constraints, Unsure
• How would you like us to balance secondary requests with the message to remaining team members about upside?
• What visibility do you need into an investor’s approach to secondary liquidity before inviting them into the process? Options: Full plan and examples, High‑level intent, Minimal—discuss later

Beyond the Wire: What Real Value Looks Like to You

• Investors promise operational help—what three specific outcomes would make you call that support transformational?
• Which portfolio operations modules would move the needle fastest for you? (pick top 2) Options: CFO + finance transformation, Go‑to‑market scaling, International expansion, Strategic M&A support, Talent & leadership hiring, Data science/analytics
• Do you want a hands‑on operating partner embedded post‑close, or a remote advisory capability? Options: Embedded operating partner, Remote advisory, Combination, Undecided
• Share an example where an investor’s ops team helped you (or a peer) in a way that mattered—what changed?
• Would you expect references from portfolio founders at a similar stage before advancing to term discussions? Options: Yes—required, Helpful but not required, Not necessary

Risk Signals & Deal Killers — Let’s Surface Them Early

• Be candid: what known risks or unresolved issues should every investor see upfront?
• Which of these is a material risk for your business today? Options: Customer concentration, Revenue recognition complexity, Regulatory/licensing risk, Key person dependency, Supply chain/partner dependency, Litigation
• Have there been recent audits, restatements, or accounting red flags we should know about? Options: Yes—significant, Yes—minor, No, Prefer to discuss privately
• If we surfaced a risk that could delay close, how would you prefer we handle communication to the board and employees? Options: Full transparency immediately, Selectively with board first, Handle privately until resolved, Other
• What mitigation steps are already in motion for your top two risks?

Decision Comfort & Next Steps — What Will Make This Easy?

• What would give you high confidence in an investor within the first two meetings? Options: Clear alignment on valuation/dilution, Strong sector track record, Operational plan for value creation, Fast diligence cadence, Reference calls with portfolio founders
• Who on your team should be involved in the next conversation and what role will each person play?
• What materials can you share within 72 hours to accelerate diligence (select all that apply)? Options: Audited financials, Cap table, Data room link, Customer metrics/KPIs, Legal documents, Other
• How would you rate your current appetite for exclusivity if it significantly shortens timeline to term sheet? Options: High—comfortable, Conditional—short window only, Low—prefer open process, Undecided
• Finally, what’s the single next step you want from us to make progress in the coming week?

• Pre-Session: Current State & Consequence Alignment
• Investor Fit Scenario Experience (Diagnosis → Proof → Validation)
• Portfolio Founder Reference Review
• Operations Playbook Mapping Workshop
• Fit Decision & Next Steps (Proceed to Deal Structure?)

• Introductions & Objectives
• Elicit explicit validation (or rejection) of each scenario and capture required adjustments or constraints.
• Identify the top 3 operational modules and metrics that matter to the customer for the next-stage planning.
• Surface any non-negotiable deal or governance requirements that would block progression.
• Firm: deliver scenario playbooks (detailed interventions, expected KPIs, timelines, and comparable portfolio case metrics) within 3 business days.
• Customer: provide feedback on each scenario's realism and list constraints or priorities to be incorporated.
• Schedule founder reference calls for cases used in the scenarios to validate outcomes and timelines.
• Reference Session Briefing
• Obtain third-party validation of the firm’s claimed outcomes and timelines in comparable companies.
• Surface practical details about operating cadence, board interactions, and personnel changes required for success.
• Identify any warning signs or mismatches that would require reassessment before proceeding.
• Firm: compile a reference dossier with verbatim founder quotes, KPI deltas, and timelines tied to each scenario.
• Customer: confirm whether the referenced outcomes change their confidence and list any remaining doubts.
• Update the scenario playbooks based on insights from founder references.
• Reconfirm Future-State & Success Metrics
• Agree a concrete 90–120 day operations plan with measurable milestones and named owners.
• Tie every ops action back to the customer's current problem and the agreed future-state outcomes.
• Surface resource requirements, estimated timelines, and any dependencies that could delay execution.
• Firm: produce the draft 100-day plan with milestones, owners, and estimated resource commitments within 3 business days.
• Customer: confirm internal owners and capacity to execute the 100-day plan or propose alternatives.
• Both: schedule a follow-up to resolve any resource or timeline gaps prior to Deal Structure discussions.
• Recap: Agreed Current State, Consequence, Future State, and 100-Day Plan
• Arrive at a clear mutual decision (proceed / pause / decline) to move to the Deal Structure stage.
• If proceeding, agree non-binding commercial guardrails and a timeline for a term sheet and exclusivity request.
• Assign owners and deadlines for the term-sheet draft, diligence kickoff, and ops 100-day activation.
• Document any final gaps that must be closed prior to structure and set explicit owners to resolve them.
• Firm: prepare a non-binding term-sheet outline and a proposed exclusivity window proposal if both sides agree to proceed.
• Customer: confirm internal approvals and availability for diligence kickoff dates and provide any remaining artifacts.
• Both: finalize the schedule for the Deal Structure & Ops Scope kickoff meeting and circulate invites with owners.
• Produce and agree on a single-sentence current-state that the entire room accepts.
• Quantify the immediate financial and strategic consequences of not addressing the problem.
• Define one clear future-state sentence that will be used to focus the Solution Experience.
• Align on decision-makers, timeline, and deliverables required for the Investor Fit Experience session.
• Founder: deliver requested datasets and one-page current-state by [date].
• Firm: prepare and circulate a one-page portfolio-case index and 2–3 relevant case summaries mapped to the customer's sector.
• Schedule the Scenario-Based Investor Fit Experience and reserve 90–120 minutes with core attendees.
• Opening Recap (Current State, Consequence, Future State)
• Show concrete, portfolio-backed pathways that prove the firm can deliver the agreed future-state in the customer's specific context.
• Review of Pre-work & Key Metrics
• Founder Reference 1 — GTM Expansion Case
• Hypothesis of Fit
• Open Issues & Deal-Readiness Checklist
• Module Mapping — GTM & Revenue Ops
• Craft the One-Sentence Current State
• Scenario A — GTM & Revenue Acceleration (Diagnosis → Proof)
• Module Mapping — Finance & IPO Readiness
• Mutual Fit Assessment
• Founder Reference 2 — IPO Readiness / CFO Advisory
• Quantify Consequences
• Synthesis: Cross-Case Outcomes & Credibility Signals
• Module Mapping — International Expansion & Legal/Compliance
• Validation Check A
• Commercial Guardrails & Proposed Timeline
• Module Mapping — Talent & Org
• Q&A and Red-Flag Resolution
• Define the One-Sentence Future State
• Agree Next Steps, Owners & Deadlines
• Scenario B — International Expansion & Margin Optimization (Diagnosis → Proof)
• Decision Map & Timeline
• Milestones, Owners & Timeline (90–120 Day Plan)

• Deploy Primary Growth Capital Tranche
• Execute Secondary Liquidity for Selling Shareholders
• Seat Investor Director on Company Board
• Place Interim CFO for Public‑Readiness
• Recruit and Onboard C‑Suite and VP Hires
• Implement Public‑Company Financial Reporting Systems
• Execute Sales Compensation and Territory Realignment
• Launch International Market Entry and Local Entity Setup
• Execute Margin Improvement and Cost‑Savings Program
• Manage Strategic M&A Transaction Execution
• Embed Portfolio Operations Pod with Management Team
• Draft and Deliver IPO Investor Presentation
• Execute Sponsor‑to‑Sponsor Secondary Sale

Deploy Primary Growth Capital Tranche

• Is a primary capital tranche required as part of this financing? Options: Yes, No, Undecided
• If yes, what is the target primary tranche size (USD or range)? Options: Less than $50M, $50M–$200M, $200M–$500M, Over $500M, Enter exact amount
• What are the prioritized uses of primary proceeds (e.g., international expansion, product R&D, M&A)?
• Are there tranche conditions or milestone-linked drawdowns (timing, KPIs, board sign-off)? Options: No – single close, Yes – performance milestones, Yes – board/consent-based, Other
• Who will own tranche execution and deliverables on the company side (role/title) and what documentation is required (funding schedule, wire instructions)?

Execute Secondary Liquidity for Selling Shareholders

• Is secondary liquidity requested in this round and for which shareholder groups (employees, founders, early investors)? Options: No secondary, Employees only, Founders only, Early investors/angels, Mixed
• What is the approximate secondary amount or percentage of equity expected to be sold (USD or %)? Options: Less than $10M, $10M–$50M, $50M–$200M, >$200M, Enter exact amount or %
• Are there preferred mechanics for secondary (co-investor facilitated, escrow, pro-rata allocations)? Options: Direct buyback by investor, Co-investor facilitated, Escrowed until close, Sponsor coordinates allocations, Other
• Do selling shareholders require tax, legal, or liquidity advisory support to execute their secondary sales? Options: Yes – tax advisory, Yes – legal advisory, Yes – liquidity structuring, No
• Are there any transfer restrictions, right-of-first-refusal, or approval processes that could affect secondary execution? Options: None known, Board approval required, Existing investors’ ROFR applies, Employee plan limitations, Other

Seat Investor Director on Company Board

• Is the expectation to take a full board seat, observer seat, or conditional observer-to-seat conversion? Options: Full board seat, Observer only, Observer to board seat on milestone, Undecided
• When should the investor director/observer take their seat (immediately at close, after governance changes, after a milestone)? Options: Immediate at close, After charter/bylaw amendment, After milestone/KPI, Other
• What are the expected governance rights and limits (voting rights, reserved matters, information rights) the investor requires?
• Who on the company side will coordinate director onboarding and materials (CRO/CFO/Company Secretary)?
• Are there any existing board composition constraints, investor consents, or staggered terms that affect seating? Options: No constraints, Staggered board terms, Consent required from existing investors, Company charter limits, Other

Place Interim CFO for Public‑Readiness

• Is an interim CFO required, and if so, what is the anticipated engagement length (months)? Options: No interim CFO needed, 3 months, 3–6 months, 6–12 months, 12+ months
• What are the top three priorities for the interim CFO (e.g., financial reporting, audit readiness, SEC filings, FP&A uplift)?
• What reporting structure and authorities will the interim CFO have (direct to CEO, full signatory rights, hire/fire authority)?
• Are there specific industry or public-company experience requirements for the interim CFO (sector, IPOs, cross-border reporting)? Options: Public company IPO experience, Cross-border reporting (IFRS/US GAAP), Scale-up CFO experience, Industry-specific experience, No specific requirement
• What immediate deliverables are expected from the interim CFO (audit-ready financials, SEC filing templates, FP&A models)?

Recruit and Onboard C‑Suite and VP Hires

• Which roles are in-scope for recruitment (check all that apply)? Options: CEO, CFO, COO, CPO/CTO, Chief Revenue Officer, VP Sales, VP Marketing, Other
• What is the target timeline to fill these roles (immediate, 30–60 days, 3 months, 6+ months)? Options: Immediate (30 days), 30–60 days, 60–90 days, 3–6 months, 6+ months
• Are these permanent hires, interim placements, or retained search mandates? Options: Permanent hire, Interim/contract, Retained executive search, Hybrid
• What are the critical success criteria for each role (experience, KPIs, cultural fit) and compensation band constraints?
• Will the firm’s operations team be involved in onboarding and 100-day plans for new executives? Options: Yes – full onboarding support, Yes – limited onboarding, No – company-led

Implement Public‑Company Financial Reporting Systems

• What accounting and ERP systems are currently in place (e.g., NetSuite, Oracle, Workday, QuickBooks)? Options: NetSuite, Oracle, Workday, QuickBooks, Custom/Other
• What gaps exist for public-company reporting (consolidation, segment reporting, stock-based comp, intercompany eliminations)?
• Is the company reporting under US GAAP, IFRS, or does it need dual reporting capabilities? Options: US GAAP, IFRS, Dual reporting required, Undecided
• Are external auditors engaged or expected (timing for first audit ready period)? Options: Audit engaged, Audit to be engaged – timeline needed, No audit planned
• What timelines and deliverables are needed (monthly close schedule, investor reporting pack, 10-Q/10-K templates)?

Execute Sales Compensation and Territory Realignment

• What are the primary goals of the sales redesign (improve coverage, align comp to ARR, reduce CAC)?
• How large is the sales organization (number of reps, managers, regions)? Options: Less than 10, 10–50, 50–200, 200+
• Do you currently have documented comp plans and quota attainment data to model changes? Options: Yes – documented and available, Partially documented, No – needs design from scratch
• Are there regulatory or country-specific constraints for comp changes (local labor laws, contractual quotas)? Options: No constraints, Yes – local labor law considerations, Yes – existing employment contracts limit changes, Unknown
• What timeline and acceptance criteria are required for rollout (pilot, phased, immediate company-wide)? Options: Pilot, Phased rollout, Immediate company-wide, Undecided

Launch International Market Entry and Local Entity Setup

• Which countries/regions are targeted for entry in the next 12–24 months?
• What local capabilities are required at launch (sales, legal entity, payroll, local leadership)? Options: Sales/BD, Local legal entity, Payroll/HR, Local leadership hire, Local finance/GA
• Do you require assistance with entity type selection, tax registration, and employment compliance? Options: Yes – full entity setup, Yes – tax/registration only, No – using local partners
• What is the target go-to-market model (direct sales, channel partnerships, distributor, local JV)? Options: Direct sales, Channel/partners, Distributor, Joint venture, Other
• What timeline and budget constraints apply to market entry and local setup?

Execute Margin Improvement and Cost‑Savings Program

• What margin targets are you aiming to achieve and over what timeframe (e.g., +500 bps in 12 months)?
• Which cost pools are highest priority (COGS, S&M, G&A, R&D, vendor spend)? Options: COGS, Sales & Marketing, G&A, R&D, Vendor/third-party spend
• Are workforce reductions or reorganizations expected or off the table? Options: Expected and acceptable, Some reorgs but no layoffs, Not acceptable
• Do you have baseline financial metrics and benchmarking to measure program savings (benchmarks, historical spend)? Options: Yes – benchmarks available, Partial data, No – needs baseline build
• What governance and reporting cadence should be used to track initiatives and capture savings? Options: Weekly steering committee, Bi-weekly updates, Monthly executive review, Other

Manage Strategic M&A Transaction Execution

• Is the M&A scope buy-side, sell-side, bolt-on integration, or divestiture? Options: Buy-side (acquisition), Sell-side (exit process), Bolt-on integration, Divestiture
• What is the target transaction size and expected timeline to close? Options: Less than $25M, $25M–$100M, $100M–$500M, >$500M, Enter exact amount
• What level of advisor support is required (financial advisor, legal, tax, IP, integration lead)? Options: Full advisor suite, Financial + legal only, Integration lead only, Other
• Are there regulatory or foreign investment approvals expected that affect timing or structure? Options: No regulatory approvals expected, Local regulatory clearances needed, CFIUS/foreign investment review, Unknown
• What post-close integration priorities and owners should be planned (systems, people, go-to-market)?

Embed Portfolio Operations Pod with Management Team

• Which portfolio operations modules are required (GTMT, finance transformation, talent, product ops, localization)? Options: Go-to-market, Finance transformation, Talent & recruiting, Product operations, Localization/market entry
• What is the expected engagement model for the pod (full-time embedded, part-time advisory, project-based)? Options: Full-time embedded, Part-time advisory, Project-based sprints, Hybrid
• Who will be the primary company sponsor and day-to-day partner for the pod?
• What measurable milestones and KPIs will define success for the operations pod (revenue lift, margin improvement, hiring milestones)?
• Do you require the pod to operate on-site, remote, or a mixed cadence, and what is the intended duration? Options: On-site, Remote, Mixed cadence, Duration: enter months

Draft and Deliver IPO Investor Presentation

• What is the target timeline for IPO readiness or roadshow (months to target)? Options: 3–6 months, 6–12 months, 12–24 months, Undecided
• What key financial and operational metrics should be highlighted in the investor presentation?
• Do you have comps and market positioning materials available, or should benchmarking be performed? Options: Comps available, Benchmarking required, Partial comps available
• Who will review and approve the draft (CEO, CFO, lead investor, external bankers)? Options: CEO, CFO, Lead investor, Investment bank, Other
• Are there confidentiality or messaging constraints for pre-IPO communications that we should observe? Options: Yes – strict controls, Moderate controls, No special constraints

• Term Sheet (Heads of Terms)
• Exclusivity / No-Shop Agreement
• Definitive Subscription / Purchase Agreement
• Investor Rights & Governance Agreement
• Conditions Precedent Schedule
• Escrow & Funds Flow Instructions
• Secondary Liquidity Allocation Agreement
• Statement of Work (Portfolio Operations)
• Side Letter(s) & Founder/Key Employee Terms
• Confidentiality & Public Announcement Protocol
• Termination & Break Fee Terms

• KPI & Success Signal Review
• Exit Readiness Gap Assessment
• 100‑Day Value Capture & Operational Milestones
• Dual‑Track Exit Strategy & Stakeholder Alignment

• Build a simple scorecard/dashboard to surface KPI trends to the board.
• Opening & Objectives
• Produce a prioritized list of exit‑readiness gaps with estimated impact and remediation timelines.
• Assign owners and initial deadlines for each top gap, and agree on required third‑party inputs.
• Align on the single‑sentence future state of readiness to use for ongoing validation.
• Draft a remediation roadmap with owners, timeline, and estimated cost for each top gap.
• Initiate requests for necessary third‑party audits or legal reviews within the agreed timeline.
• Share targeted portfolio case studies and playbooks relevant to the top 3 gaps.
• Opening & Plan Objective
• Agree on the top 6 initiatives and measurable milestones for the next 100 days.
• Define expected KPI impacts at 30/60/100 day intervals and owners for each initiative.
• Confirm resource needs and a governance cadence for progress reviews.
• Publish the 100‑day plan with RACI, milestones, metrics and reporting cadence.
• Kick off top two initiatives within 7 business days and confirm interim deliverables.
• Set up the weekly KPI dashboard distribution and executive checkpoint calendar invite.
• Opening & Desired Decision
• Get alignment on whether to run dual‑track or commit to a specific exit path.
• Define explicit decision triggers, timeline, and owners to move from optionality to execution.
• Agree on a stakeholder communication plan to preserve valuation and optionality.
• Deliver scenario model workbook with sensitivity analysis and recommended preferred path.
• Draft board memo outlining triggers, recommended timetable, and communication plan for approval.
• Schedule standing alignment calls (weekly/biweekly) until the decision trigger is resolved.
• Confirm a one‑sentence current state that all stakeholders accept.
• Agree on the 6–8 primary KPIs that define exit readiness and set target thresholds.
• Quantify immediate valuation or timing consequences for the top KPI gaps.
• Assign owners and reporting cadence for each primary KPI.
• Document and circulate agreed KPI definitions, targets, and dashboard wireframe.
• Assign owners and a weekly reporting cadence for each KPI.
• Opening & Objectives
• One‑sentence Current State
• One‑sentence Current Exit Position
• One‑sentence Current Initiative State
• One‑sentence Current Readiness State
• Prioritized Initiatives & Milestones
• Domain Gap Identification
• KPI Deep Dive
• Scenario Modelling: IPO vs Strategic Sale
• Proof of Impact Modeling
• Consequence & Timing Impact
• Define Decision Triggers & Timing
• Map KPIs to Success Signals
• Consequence Modelling
• Stakeholder Communication & Board Alignment
• Resourcing, Dependencies & Risk Mitigation
• Define Future‑State Exit Checklist
• Validation & Agreement
• Proof Points & References
• Validation & Next Steps
• Validation & Weekly Cadence
• Agree Prioritization & Next Steps