Quick orientation: your current growth moment

• Tell me briefly how you would describe your current growth moment and the decision that brought you to consider outside growth capital.
• How many millions of ARR does your business currently run on, and how stable has that figure been over the past 6 months? Options: $5–10M, $10–20M, $20–35M, $35–50M, Above $50M, Prefer to state exact number
• Walk me through your most important revenue streams or customer segments and which one you expect to scale first.
• Across acquisition, onboarding, retention, and expansion, point to the one or two stages that drive most of your revenue variability. Options: Acquisition, Onboarding, Early retention (0–3 months), Mature retention (12+ months), Expansion/upsell, Other
• Count the number of full-time sellers and account managers you have today and summarize how quota attainment is trending.
• If you had to name the single operational change that would accelerate your path to a successful next round, what would it be?

Where the numbers bite: retention, unit economics, and sales efficiency

• Which metric, if it worsened by 5 percentage points next quarter, would force you to rethink your growth plan? Options: Net retention rate, Gross retention rate, LTV to CAC, CAC payback, Sales efficiency (SaaS magic number), Other
• Give the retention rates by cohort for customers acquired in the last 24 months and note any major divergence between cohorts.
• Select the range that best describes your current LTV to CAC ratio. Options: <1.5, 1.5–2.5, 2.5–4, >4, Do not know / need to calculate
• How long does it take on average for a new sales rep to reach quota, and what ramp investments do you provide? Options: <3 months, 3–6 months, 6–9 months, >9 months
• If your unit economics do not materially improve within 6 months, would you prioritize price increases, sales productivity, product changes, or cost reduction to hit targets? Options: Price increases, Improve sales productivity, Product changes, Reduce costs, Other
• What single financial threshold or KPI, if unmet after a three-month pilot, would lead you to stop pursuing this capital and operational partnership?

Who owns the decisions, and who can block them

• If you brought on an investor who took a board seat, what would you expect that board member to do differently in the first 90 days to change outcomes?
• Who on your executive team owns go-to-market, international expansion, finance, and talent acquisition today? Select all that apply and add names if helpful. Options: Head of Sales / Chief Revenue Officer, CEO, Head of Growth / CMO, CFO, Head of People / CHRO, VP Engineering, Other
• Count your open senior roles (VP-level and above) and list the top two hiring priorities.
• Walk me through your current board composition, including investor and independent seats, and any governance expectations that matter to you.
• If a key executive required by the scaling plan cannot be hired within 90 days, what contingency would you accept instead? Options: Interim hire, Contracted advisor, Reprioritize plan, Pause hiring, Other
• Who has veto power over bringing a new board member, and if they oppose it, would you still proceed with the partnership? Options: Yes, proceed, No, need unanimous support, Depends on terms, Unsure

Where execution can break: realistic obstacles that derail plans

• What single execution risk could erase the upside you are projecting for the next 12 months?
• When you try to expand into a new country, what operational or legal hurdles have caused the longest delays in the past?
• Are there enterprise contracts or channel agreements with change-of-control clauses that could complicate an investment or board change? Options: Yes, several, Yes, a few, No known issues, Unsure
• How dependent is your stack on a single third-party vendor for billing, identity, or payments, and how would a vendor outage affect revenue? Options: Very dependent, Somewhat dependent, Minimal dependency, No single dependency
• Describe a recent incident that exposed a weakness in scaling the product, go-to-market, or operations and what you changed because of it.
• If a regulatory review were initiated in a target market, would that stop your international launch plans or delay them, and by how long? Options: Stop entirely, Delay by 3–6 months, Delay by 6–12 months, Manageable impact under 3 months, Unsure

The other options on your table

• Point to the option on the table that feels most likely to deliver what you need: your current investor increasing their check, a new growth lead, or scaling with internal cash. Why? Options: Current investor increases check, A different growth investor, Self-fund with existing cash, Strategic partnership, Other
• List any external firms or investors you have spoken to or are evaluating and the primary reason each remains in consideration.
• Has someone on your team proposed solving this need without an outside partner, and if so, what is the proposed route? Options: Yes, internal plan exists, No internal plan, Discussion underway
• What would have to be true about your current approach for you to decide to stay the course rather than take outside capital?
• Are there incumbents or competitors that founders commonly point to as preferred partners, and what specifically attracts you to them?
• If the incumbent investor matched every governance term but did not provide the operational support you desire, would matching governance be enough for you to stay? Options: Yes, governance is enough, No, operational support is required, Depends on valuation, Unsure

Can your systems and team actually run this plan

• Point to the systems, permissions, or internal owners that must be available from day one for a board-led scaling program to start smoothly.
• Select the categories of systems we will need access to, such as your primary CRM, billing platform, customer data warehouse, and identity provider. Options: Primary CRM, Billing/payment system, Customer data warehouse, SSO/identity provider, Marketing automation, ERP/financial system, Other
• Do APIs exist for those systems and who manages them in your organization? Options: Yes, internal engineering owns them, Yes, vendor-managed connectors, Partial APIs with gaps, No APIs, Unsure
• How clean and connected is your customer and revenue data for cohort analysis on a scale from 1 to 5? Options: 1 - Poor, 2 - Below average, 3 - Mixed, 4 - Mostly clean, 5 - Ready for advanced analysis
• Who would be the primary technical owner we coordinate with, and are they available for weekly alignment during a 6 to 12 week diligence and pilot phase? Options: Yes, fully available, Partly available, Not available, Need to assign
• If you could not assign a data owner with access to revenue cohorts within 2 weeks, would that delay the engagement or stop it entirely? Options: Stop entirely, Delay by more than 4 weeks, Delay by 1–4 weeks, Manageable

Choosing between faster growth and cleaner economics

• If the next investor required a three-year plan showing either faster ARR growth with lower margins or slower growth with higher profitability, which path would you choose and why? Options: Faster growth, accept lower margins, Slower growth, improve margins, Balanced approach, Undecided
• How aggressive are your growth targets for the next 12 and 24 months in percentage ARR growth? Options: >100%, 50–100%, 25–50%, 10–25%, <10%
• What is your target timeline to the next financing event or liquidity outcome? Options: 6–12 months, 12–18 months, 18–36 months, More than 36 months, Undecided
• How comfortable are you with taking a lead investor who requires a board seat and active operational involvement? Options: Very comfortable, Somewhat comfortable, Prefer limited involvement, Opposed
• What level of dilution are you and your current investors willing to accept to reach the growth outcome you want? Options: <10%, 10–20%, 20–30%, >30%, Undecided
• If an investor offered the capital but insisted on replacing one of your senior GTM hires, would you accept the condition to close the round? Options: Yes, No, Maybe depending on the role

Decision points and timeline to move forward

• If we proved the impact of our program in a short pilot, what would be the single fastest path to a signed agreement from your side?
• Who are the three stakeholders whose buy-in is required to sign, and what concerns does each have?
• What specific acceptance criteria must a pilot meet for you to authorize full engagement, for example revenue lift, CAC payback, retention improvement, or a VP hire placed on time? Options: Revenue lift by %, Reduced CAC payback, Improved retention cohorts, VP hire within timeline, Other
• Realistically, what is your ideal timeline to close if commercial and governance terms align? Options: Immediately (weeks), 1–2 months, 2–3 months, 3–6 months, Longer
• What budget approvals or legal reviews are required before you can sign, and how long do they typically take?
• If everything checks out in a two-month diligence and pilot, who can sign the final agreement and would they be ready to do so within your ideal timeline? Options: Yes, authorized signatory ready, Needs board approval, Requires investor consent, Unsure

• Scaling Strategy Workshop

• Confirm the current state and its cost
• You confirm the diagnosed bottlenecks and agree on the direct cost to ARR, CAC, or timing risk.
• Seller to deliver a tailored 12-month scaling plan with capital allocation, hiring timeline by role, and expected retention and CAC payback KPIs within five business days.
• You confirm the proposed capital allocation and hiring timeline will materially address the scaling bottlenecks when combined with the board partnership and platform support.
• Align priorities and constraints
• Buyer to provide top three priority international markets and current cohort retention and CAC payback by vintage before the seller creates the market sequencing plan.
• Seller to run a sensitivity model showing ARR outcomes under three hiring pace scenarios and share the results before the follow-up decision meeting.
• You confirm the board role responsibilities, decision rights, and meeting cadence align with your governance needs during the scaling window.
• Run a capital allocation and hiring scenario
• Walk through the board partnership and governance model
• You agree on the specific evidence and remaining open questions required to move toward a term discussion.
• Buyer to identify any governance red lines or board composition preferences that would block the proposed board role.
• International launch playbook and sequencing
• Validate the plan with a forced confirmation

• Scaling Strategy Workshop
• Scaling Strategy Deck
• Scaling Strategy Brief

• meeting
• slides
• document

• Lead Round Investment and Execute Term Sheet
• Take Board Seat and Attend Board Meetings
• Deploy Go-to-Market Scaling Playbook
• Recruit and Place VP-Level Sales Leaders
• Recruit and Place VP-Level Functional Leaders
• Onboard Interim Sales Leadership
• Design and Implement Sales Compensation Plan
• Build Investor-Ready Financial Models and Deck
• Provide International Expansion Playbook and Launch Support
• Manage M&A Advisor Coordination and Due Diligence Support
• Implement Sales Operations and KPI Dashboards
• Provide Portfolio Founder Introductions and References

Lead Round Investment and Execute Term Sheet

• Do you have an up-to-date cap table schedule that reflects all option pools and convertible instruments? Options: Yes, No
• How much capital are you seeking in this round (USD) and what minimum tranche on your cap table should be reserved for the lead investor?
• Which preferred share terms in your current term sheet draft are non-negotiable (for example liquidation preference, anti-dilution, pro rata)? Options: Liquidation preference, Anti-dilution, Pro rata rights, Board composition, Other
• Provide the folder path in your data room for the legal documents we must review (for example charter amendments, investor rights agreement, convertible instrument documents).
• What evidence will validate readiness to execute the term sheet (for example signed commitment letters from existing investors, counsel sign-off on organizational documents, updated cap table schedule)? Options: Signed commitment letters, Legal counsel sign-off, Updated cap table schedule, All of the above
• Who on your team is authorized to negotiate economic and governance terms and what email should appear in the term sheet signature block?

Take Board Seat and Attend Board Meetings

• Have you published a board charter or governance document that specifies seat allocation, observer rights, and voting thresholds? Options: Yes, No
• How many board meetings per year are in your current cadence and what is the typical board pack lead time (for example 7 days prior to the meeting)? Options: Quarterly (4), Monthly, Bi-monthly, Custom
• Select the responsibilities you expect an incoming director to own from day one (for example GTM strategy review, hiring approval for VP roles, fundraising stewardship). Options: GTM strategy review, Hiring approvals for VP roles, Fundraising stewardship, Financial oversight / budgeting, Other
• Identify any existing board committee structures we must slot into and provide the names or file paths of the committee charters (for example audit, compensation, nominating).
• When should the new board member begin attending meetings relative to the funding milestone (for example at signed term sheet, at close, after first capital draw)? Options: At signed term sheet, At close, After first capital draw
• What acceptance criteria will confirm board onboarding completion (for example signed director consent, completed background check, delivery of initial board slide deck)? Options: Signed director consent, Background check completed, Delivery of initial board deck, All of the above

Deploy Go-to-Market Scaling Playbook

• Describe your top three buyer personas and include current average deal size and median sales cycle length from your CRM for each persona.
• Indicate your current pipeline coverage ratio and recent quota attainment by Account Executive cohort as recorded in your CRM. Options: <2x, 2-3x, >3x, Unknown
• Select the playbook modules you require for scaling (for example territory design, SDR motion and scripts, inbound qualification flows, partner channel program). Options: Territory design, SDR motion and scripts, Inbound qualification, Partner channel program, Renewals / CS playbook
• Provide the current SDR and AE ramp timelines (in months) and the onboarding checklist location used to certify a rep as productive.
• List the retention and expansion metrics you use in models (for example cohort retention table, net revenue retention percentage at 12 months) and supply the source file path.
• Who will own execution of the playbook inside your organization and which operational systems (CRM, cadence tool, compensation system) will they have admin access to?

Recruit and Place VP-Level Sales Leaders

• Have you prepared an approved job description and 90-day success metrics for the VP of Sales role; if so, attach the JD link or data room path. Options: Yes, No
• Specify the total on-target earnings (OTE) range and the intended equity grant (percentage or option pool) for the VP Sales role.
• List the required interview stages for this hire (for example hiring manager screen, CEO panel, board interview, reference checks). Options: Hiring manager screen, CEO panel, Board interview, Reference checks, Technical / case review
• Indicate how many internal stakeholders will sit on the interview panel and who will make the final hiring decision.
• State the target close timeline for the hire (in weeks) and any mandatory background experience required (for example enterprise sales, international expansion). Options: 4-8 weeks, 8-12 weeks, 12+ weeks
• Are relocation support, visa sponsorship, or local entity employment conditions required for candidates in priority regions? Options: Yes, No

Recruit and Place VP-Level Functional Leaders

• Select which functional VP roles you plan to prioritize this year (for example VP Product, VP Engineering, VP Customer Success, VP Finance). Options: VP Product, VP Engineering, VP Customer Success, VP Finance, VP Marketing
• Attach or link the key deliverables and 90-day success metrics for each prioritized functional leader (for example product roadmap milestones, GAAP month-end close).
• Describe the approval process for external hires versus internal promotions for these leadership roles.
• Identify the compensation benchmarking sources you prefer for offer construction (for example stage-comparable equity multiples, market percentile surveys).
• Specify any compliance or credential requirements per role (for example GAAP expertise for VP Finance, GDPR product experience for VP Product) and point to relevant documents.
• Name the hiring owner for each role and state who in your organization holds offer-signing authority.

Onboard Interim Sales Leadership

• Will you require an interim sales leader to start before the permanent hire and if so for how many months? Options: No, 1-3 months, 3-6 months, 6+ months
• State the specific objectives the interim leader must achieve (for example improve pipeline-to-opportunity conversion by X percentage points, reduce sales cycle by Y days).
• Detail the access requirements for the interim leader including CRM admin rights, commission reports, and sales compensation spreadsheets and provide data room locations.
• Name the existing sales and CS team members who will report to the interim leader and define the decision rights that the interim leader will hold.
• Choose the compensation structure for the interim leader (for example monthly retainer, short-term equity, success fee, or a combination). Options: Monthly retainer, Equity grant, Success fee, Combination
• When should the interim leader start relative to close (for example immediately on close, 30 days after close, at the start of the next fiscal quarter)? Options: Immediately on close, 30 days after close, Start of next quarter

Design and Implement Sales Compensation Plan

• Have you documented an existing sales compensation plan that includes quota, OTE, accelerators, and any SPIFFs? Options: Yes, No
• State the target quota attainment percentages and commission accelerator tiers you expect for Account Executives and SDRs.
• Choose the commission payout frequency that you currently use for sales roles and name the payroll or commission system that processes payouts. Options: Monthly, Quarterly, Other
• Attach your climb schedule and new-hire ramp quotas or paste the key values used during rep onboarding.
• Confirm whether quota relief or split-credit rules exist for expansion ARR, renewals, or cross-sell and link the policy document. Options: Yes, No
• Confirm the approver(s) for compensation plan changes and list the board materials required when a material change is proposed.

Build Investor-Ready Financial Models and Deck

• Do you maintain a three-statement financial model (profit and loss, balance sheet, cash flow) in a shared spreadsheet and if so where is it located? Options: Yes, No
• Provide the last twelve months of monthly recurring revenue (MRR)/annual recurring revenue (ARR) by cohort and point to the retention cohort table used in your model.
• Which modeling assumptions should we use for CAC payback, gross margin, churn, and ARR growth rates over the next 24 months?
• What evidence will confirm the investor-ready model meets expectations (for example scenario tabs, audit trail of changes, reconciled cap table and source schedules)? Options: Scenario tabs included, Audit trail available, Reconciled cap table and schedules, All of the above
• Which investor audiences will this deck target and which appendix materials are required (for example detailed unit economics, GTM KPIs, customer reference list)? Options: Growth investors, Crossover investors, Strategic acquirers, Other
• Who on your finance team can validate forecasts and who will provide final sign-off on the deck and model?

Provide International Expansion Playbook and Launch Support

• Which target countries or regions are highest priority for expansion in the next 12 months and what ARR targets do you assign to each market?
• Do you already have local entities, distributor agreements, or reseller contracts in these markets; if yes attach entity registration or contract file paths. Options: Yes, No
• Select the regulatory or tax artifacts that must be addressed per market (for example VAT registration, data residency, local employment law compliance). Options: VAT registration, Data residency requirements, Local employment law, Industry-specific regulation
• Provide the intended go-to-market channels per country (for example direct sales, local channel partners, reseller networks) and estimate the timeline to first revenue per market.
• Choose the level of localization required for product, pricing, and contract language in each market. Options: Full localization (product, pricing, contracts), Partial localization (pricing and contracts), English-only initially
• Who will act as the market lead for each country and what local hiring or contractor arrangements are acceptable under your employment policies?

Manage M&A Advisor Coordination and Due Diligence Support

• Do you anticipate pursuing tuck-in acquisitions as part of growth and what is your target deal size range (revenue or enterprise value)? Options: No, < $5M, $5M - $20M, > $20M
• Provide the data room folder path for M&A diligence materials and the primary contact for any external advisors.
• Which integration artifacts will be required post-close (for example customer contracts with assignment language, IP assignment records, single sign-on integration plans)?
• Select which due diligence areas should be prioritized by advisors (for example technology audit, customer reference checks, financial forensic review). Options: Technology audit, Customer references, Financial forensics, Legal / IP review
• Who will lead internal diligence coordination and what is your preferred cadence for advisor check-ins during due diligence?
• Are there any non-negotiable post-acquisition employment conditions or retention bonus structures that must be honored for key hires? Options: Yes, No

• Subscription / Share Purchase Agreement
• Shareholders' Agreement
• Board Seat Appointment Letter
• Valuation & Purchase Price Mechanics Exhibit
• Closing Conditions, Deliverables & Schedule
• Disclosure Schedules & Compliance Certificates
• Escrow and Holdback Agreement
• Side Letter / Special Commitments

• Post-Investment Go-live Health Check
• First Outcomes Measurement
• 90-Day Acceptance Gate
• Quarterly Partnership Review

• Close or reassign top three operational tickets and update their status in the shared partnership channel with new deadlines.
• Produce a metric variance report showing root causes for each gap versus Investment Scope targets.
• Create a prioritized remediation plan with owners, milestones, and a target completion date before the 90-day gate.
• Update the shared partnership channel with an agreed triage order and expected resolution dates for open operational tickets.
• Restate acceptance criteria and numeric targets recorded in Investment Scope
• Capture a documented pass or fail decision for each acceptance criterion and record the buyer's signatory decision when required.
• For any failed criteria, agree a remediation plan with named owners and dates that closes the loop within an agreed timeframe.
• If acceptance is achieved, confirm the handoff to the ongoing realization cadence and reporting responsibilities.
• Publish the acceptance decision and evidence packet to the shared workspace with signatory confirmation where applicable.
• List remediation tasks for failed criteria with owners and target resolution dates, and schedule a mid-point checkpoint.
• Set the schedule and reporting template for the Quarterly Partnership Review.
• KPI trend review against Investment Scope targets
• Confirm whether Net Revenue Retention and ARR growth rate are on trajectory to meet Investment Scope targets or require escalation.
• Ensure recruiting progress is sufficient to support the go-to-market plan and document any additional resourcing needs.
• Reduce the number of high-severity open operational issues and shorten average time to resolution through agreed actions.
• Publish a quarterly performance summary comparing actuals to Investment Scope targets and circulate to board members and leadership.
• Create a 90-day hiring plan for outstanding VP-level roles with milestones and expected start dates.
• Re-confirm post-close responsibilities and owners
• All critical post-close checklist items have named owners and target completion dates.
• Any launch blockers have remediation actions with committed timelines documented in the shared channel.
• Board onboarding and first reporting deliverables are scheduled and accessible to participants.
• Publish an updated post-close checklist with owners and dates to the shared partnership channel.
• Open remediation tickets for each blocker and assign target resolution dates.
• Confirm VP-level recruiting brief and handoff to the talent team for active sourcing.
• Present first measurement of ARR growth rate and Net Revenue Retention
• Determine whether ARR growth rate and Net Revenue Retention are tracking toward Investment Scope targets or require remediation.
• Document a set of corrective actions with owners and dates so the team reaches the acceptance gate on schedule.
• Confirm recruiting priorities and next steps for any open talent requests affecting go-to-market capacity.
• Present outcome data against each acceptance criterion
• Talent and organizational readiness update
• Board onboarding and governance readiness
• Root-cause diagnosis for any metric gaps
• Document pass or fail per criterion and capture formal acceptance decision
• Operational access and platform enablement
• Operational issues and shared channel metrics
• Agree corrective actions and timeline to the acceptance gate
• Agree remediation plan for any failed criteria
• Early adoption signals and recruiting kickoff
• Review talent request and recruiting progress
• Governance and board action item review
• Triage outstanding operational issues in the shared channel
• Agree next quarter priorities and owners
• Open blockers from the shared partnership channel
• Transition to ongoing realization tracking
• Agree immediate remediation actions and timelines