Quick Intro: Where You Are Right Now

• In one sentence, how would you describe where the company is today (stage, core product, and immediate focus)?
• What is your current ARR today? Options: <$5M, $5M–$10M, $10M–$25M, $25M–$50M, >$50M
• How would you describe your primary GTM motion right now? Options: Field sales / enterprise-led, Mid-market sales, SMB / inside sales, Self-serve / product-led, Channel / partners, Hybrid
• Who are your core customers and what problem do you solve for them (name 1–3 personas or verticals)?
• What was your ARR growth rate over the last 12 months? Options: >100%, 50–100%, 25–50%, 10–25%, 0–10%, Negative
• Which of these best describes your current fundraising objective for this stage? Options: Lead a growth/Series B round, Join as a co-lead, Competitive process (multiple incoming terms), Exploratory conversations only, Bridge / extension

Is Growth Hiding a Problem?

• You’re growing — but which metric, if it slipped tomorrow, would reveal that growth isn’t durable? Options: Net revenue retention, Gross retention / churn, Sales efficiency (LTV:CAC), Average contract value (ACV) trends, Burn / runway
• What is your current Net Revenue Retention (NRR) or closest equivalent? Options: ≥130%, 120–129%, 110–119%, 100–109%, 90–99%, <90%, I don’t have this number
• What are the primary causes of churn or contraction in your customer base? Options: Price/ROI concerns, Product fit gaps, Competition, Operational onboarding issues, Customer personnel changes, Other
• How have your retention cohorts trended over the last 6–12 months? Give a brief example of one cohort that surprised you.
• How long have these retention or churn dynamics been affecting growth? Options: Just emerged (≤3 months), Recent (3–6 months), Sustained (6–12 months), Longstanding (>12 months)
• What single change would most move the needle on retention for you this year?

Where the Board Needs to Add Real Value (Not Just Heads on Paper)

• If your board didn’t show up for the next quarter, what would break — and why does that matter?
• Who currently sits on your board and what roles do they play? Options: Founder(s), Existing lead investor(s), Independent industry exec(s), Operational partner(s), No formal board yet
• What do you most need from a new board partner in the next 12 months? Options: GTM playbook and introductions, VP-level recruiting help, International expansion experience, Fundraising & capital markets guidance, M&A advisory, Operational transformation
• Which board meeting cadence and involvement style would feel most useful right now? Options: Monthly, hands-on, Quarterly, strategic, Quarterly + working sessions as needed, Mostly ad-hoc
• Tell us about a time your board helped (or hurt) a critical initiative — what happened and what did you learn?
• What intangible traits matter most in a board partner (e.g., honest direct feedback, network access, sector credibility)? Options: Operational owner mentality, GTM credibility, Capital markets experience, Founder empathy, Network access

The Capital Conversation: Beyond the Check

• Imagine the round closed tomorrow with no operational support — why would that be a problem for hitting your 12–18 month targets?
• How much capital are you looking to raise (or want us to lead) in this round? Options: $5–20M, $20–35M, $35–50M, $50–75M, >$75M, Undecided
• What is the primary use of proceeds you expect from this raise? Options: Scale sales team, International expansion, Product development / R&D, Strategic M&A, Extend runway / ops stability, Other
• How many months of runway will this raise deliver at current burn? Options: <6 months, 6–9 months, 9–12 months, 12–18 months, >18 months
• Which post-investment supports would be most valuable to you (pick top 3)? Options: Dedicated talent recruiting for exec hires, GTM playbooks & sales ops support, International expansion playbook + introductions, Financial planning & IPO readiness, M&A strategy and targets, Customer introductions
• What governance or board terms would be a hard requirement for you to accept (e.g., board seat, veto rights, protective provisions)?

Who Else Needs to Sign Off — And When?

• If one key stakeholder pushed back on this deal, would your timeline materially slip — and how long might that delay be? Options: No delay, 2–4 weeks, 1–2 months, 2–3 months, Longer / unknown
• Who are the decision-makers that must approve this transaction? Options: CEO / Founder(s), Board Chair, Existing lead investor(s), CFO / Finance committee, Other strategic partner(s)
• Are there any investor dynamics (e.g., pro-rata fights, preferred rights, existing liquidation preferences) that could complicate closing? Options: Yes, likely, Possibly, No, Unsure
• What is your target timeline for signing a term sheet and for legal close? Options: Sign term sheet within 2 weeks, Sign within 1 month, 1–2 months, 2–3 months, Longer / rolling
• How would you like diligence and discovery to run (pace, reference calls, data-room model)? Options: Fast-track focused diligence, Standard paced diligence, Rolling diligence with staged deliverables, Prefer exploratory conversations first

Scaling GTM & Talent: What Keeps You Awake at Night

• Is hiring your next VP of Sales (or equivalent) a make-or-break priority — or is there a different role that would unlock growth faster? Options: VP Sales / CRO, Head of Customer Success, Head of Ops / RevOps, Head of International, Product leadership, Multiple equally urgent
• Which senior hires are open today and how long have those searches been running?
• What have been the biggest barriers to closing senior hires (compensation, culture fit, speed, competing offers, network)? Options: Compensation / equity, Cultural fit concerns, Hiring speed, Candidate pipeline quality, Counter-offers / competition, Other
• Have you worked with an external talent team or platform before? What worked and what didn’t? Options: Yes — very effective, Yes — mixed results, Tried and stopped, Never
• If we were to prioritize three GTM changes in the next 90 days to accelerate growth, what would they be?
• Which GTM metrics do you monitor weekly and which are feeling most fragile (list 1–3)?

What Would a Successful Partnership Actually Look Like?

• If we partnered and after 12 months you felt it hadn't moved the needle, what would you say went wrong?
• What are the top three outcomes you would expect from an ideal investor partner in the first year? Options: >X% ARR growth (specify), Improved NRR / retention, Headcount scaled with key hires, Successful international launch, Clear path to next round / IPO readiness, Strategic M&A executed
• Which KPIs should we commit to tracking together as the single source of truth? Options: Net Revenue Retention (NRR), Gross retention / churn, New ARR / bookings, ACV / ASP, Sales efficiency (LTV:CAC, payback), Burn multiple
• Who on your team should own the first 90-day joint plan and which named roles are accountable for each milestone?
• How comfortable are you with the investor taking an active operational role (hands-on vs. strategic only)? Options: Very comfortable — want hands-on help, Prefer strategic advisory with some support, Mostly strategic / governance only, Unsure
• Would you be willing to share two founder references who can speak to how you collaborate and handle hard feedback? Options: Yes — provided now, Yes — can provide on request, Maybe later, No

• Founder Context & Impact Diagnosis
• Board Partnership Scenarios & Governance Workshop
• GTM Playbook Simulation — Revenue Scaling Scenarios
• Talent & Org Design Workshop
• Capital Use & Outcomes Modeling

• Document explicit board responsibilities, cadence, and decision-rights tied to scaling milestones.
• Firm to propose one or two named partner candidates for the board seat and share short bios + relevant portfolio outcomes.
• Draft a board charter outlining meeting cadence, deliverables, and escalation paths for the first 12 months.
• Schedule reference calls with 1–2 founders from portfolio companies who experienced the proposed board model.
• Confirm Diagnosis & Chosen Scenario
• Re-affirm Diagnosis & KPIs
• Select a primary GTM playbook and commit to a measurable 90/180-day execution plan.
• Agree expected ARR and unit-economics improvements tied to the chosen playbook.
• Identify owners for each major GTM activity and the primary KPIs we will track weekly/monthly.
• Firm GTM lead to deliver a one-page 90-day GTM playbook with named owners and KPI dashboard.
• Founder to confirm internal owner assignments and provide access to sales pipeline tools for tracking.
• Schedule a 30-day check-in to review early indicators and adjust the playbook based on live data.
• Confirm Chosen GTM Playbook & Critical Roles
• Agree on the top-priority hires, their success metrics, and a realistic time-to-hire schedule.
• Commit to using the firm's talent resources for named roles and accept the proposed org design.
• Define onboarding and 90-day performance milestones for each critical hire.
• Talent team to open recruiting pipelines for the top 2 roles and share candidate profiles within 7 business days.
• Founder to provide interview panel and availability; agree on compensation bands for each role.
• Create 30/60/90 onboarding templates and KPI checklists for each hire and share with the founder.
• Re-Confirm Future State & Key Milestones
• Agree on a preferred capital scenario (check size, use-of-proceeds, and tranches) that aligns to the execution plan.
• Understand ownership and dilution implications for founders and existing investors under the chosen scenario.
• Confirm milestone definitions that will gate tranche releases or board commitments.
• Finance lead to deliver a 3-scenario financial model showing runway, dilution, and milestone-linked KPIs within 3 business days.
• Draft a term-outline that reflects the preferred capital scenario, governance expectations, and board composition for discussion in Mutual Commit.
• Schedule a joint session with founder CFO to validate model assumptions and finalize milestone definitions.
• Lock a crystal-clear one-sentence current state that all parties will use as the baseline.
• Surface and quantify the business consequence in concrete financial and operational terms.
• Agree a single, measurable future-state outcome to prove against during the Partnership Experience.
• Agree which founder-specific scenarios (e.g., enterprise expansion, international launch, product adjacencies) we will model in follow-up sessions.
• Founder to share ARR, retention cohorts, LTV:CAC, sales ramp and pipeline metrics within 48 hours.
• CustomerNode / Firm to prepare a one-page diagnosis summary (current state, consequence, future state) for validation.
• Select 1–3 founder-specific scenarios to simulate in the next meetings.
• Agree the preferred board participation model that best enables the agreed future state.
• Introductions & Objectives
• Confirm references and case studies that validate the firm’s ability to deliver the promised board value.
• Current Org & Gaps
• Capital Scenarios Overview
• One-Sentence Current State (Diagnosis)
• GTM Playbook Options
• Board Model Options Overview
• Time-to-Hire & Cost Consequence
• Financial Modeling & Dilution Impact (Proof)
• Modelled Outcomes (Proof)
• Quantify Consequence
• Founder-Specific Scenario Mapping
• Recruiting Playbook & Sourcing Proof
• One-Sentence Future State
• 90/180-Day Execution Plan
• Tranches, Governance & Operational Support
• Proof via Portfolio Case Studies
• Org Design & Ramp Plan
• Evidence Review
• Governance & Decision Rights Discussion
• Risk & Mitigation Brainstorm
• Tie Capital to GTM & Talent Execution
• Validation & Next Steps
• Validation & Preferred Model Selection
• Validation Questions
• Validation & Hiring Prioritization

• Assume Board Seat
• Lead Series B Term Sheet Negotiation
• Execute VP of Sales Recruitment
• Deploy Interim CRO
• Deploy SDR Team and Enablement
• Deliver Sales Playbook and Battlecards
• Implement Salesforce Pipeline and Dashboards
• Build Investor-Ready Financial Model and Cap Table
• Manage Investor Roadshow and Pitch Deck Delivery
• Run M&A Process and Buyer Outreach
• Provide Fractional CFO (3–6 months)
• Launch International GTM Pilot (country)

Assume Board Seat

• Are you open to an investor taking a board seat as part of this round? Options: Yes, No, Maybe / Conditional
• What board composition are you targeting after the investment? Options: Founder-led majority, Investor(s) + founders balanced, Independent chair + investors, Other (please specify)
• What specific board role would you expect the investor to fill? Options: Observer, Non-executive board member, Board member with committee responsibilities, Chair / Lead director, Undecided
• What governance responsibilities and decision rights should the investor board seat carry (e.g., hiring approvals, budgets, M&A consent)?
• Do you have existing board governance documents, shareholder agreements, or protective provisions we should align with? Options: Yes - will share, No, In progress
• What meeting cadence and reporting expectations do you foresee for the new board seat? Options: Monthly, Quarterly, Ad-hoc / as-needed, Hybrid (regular + ad-hoc)

Lead Series B Term Sheet Negotiation

• What is your target check size or the range you expect from the lead investor? Options: $5M-$10M, $10M-$20M, $20M-$50M, $50M+
• Do you have a target pre-money valuation range or anchor you want the lead to negotiate to?
• Which deal structures are acceptable/preferred (pick all that apply)? Options: Preferred equity, Common equity, Convertible instrument, Other / custom structure
• Which investor protections or covenants are non-negotiable for you (e.g., liquidation preference, anti-dilution, protective provisions)?
• Which economic or governance terms are you willing to be flexible on during negotiation? Options: Price / valuation, Board composition, Liquidation preference, Pro-rata / follow-on rights, None / prefer fixed
• What is your desired timeline to finalize key term sheet points? Options: Under 2 weeks, 2-4 weeks, 1-2 months, Flexible

Execute VP of Sales Recruitment

• Are you actively recruiting a VP of Sales now or planning to start recruitment soon? Options: Actively recruiting, Planned within 30 days, Planned within 1-3 months, Not currently planning
• What profile do you want for the VP of Sales (experience level, ARR scale, industry specialization)?
• What compensation mix do you prefer for this role? Options: Base + Commission + Equity, Equity-heavy (lower base), Base + Equity (limited commission), Other / flexible
• Do you want the firm to run end-to-end recruiting (sourcing, interviewing, reference checks, offer) or provide a shortlist only? Options: End-to-end (full service), Shortlist + interview support, Advisory only
• What are the key performance milestones and ramp timeline you expect for the VP of Sales (quota, hiring, pipeline targets)?
• Are there internal recruiting stakeholders or constraints (comp plan approval, board sign-off) we should coordinate with? Options: Yes - specify, No

Deploy Interim CRO

• Do you require an interim CRO to translate strategy into execution immediately? Options: Yes - full-time interim, Yes - part-time/advisory, No
• What expected duration do you have in mind for an interim CRO engagement? Options: 1-3 months, 3-6 months, 6+ months
• What are the primary objectives for the interim CRO (e.g., restructure GTM, hire leadership, improve forecasting)? Options: Build GTM structure, Hire & ramp sales leadership, Improve forecasting and ops, Prepare for fundraising or M&A, Other (please specify)
• What level of operational authority should the interim CRO hold (hiring/fire, budget approval, P&L responsibility)? Options: Full operational authority, Limited authority with board approval, Advisory only
• Which KPIs will define a successful interim CRO engagement (e.g., pipeline growth, quota attainment, hires closed)?
• Are there any conflicts, non-competes, or availability constraints we should be aware of for candidates? Options: Yes - will disclose, No

Deploy SDR Team and Enablement

• What is your current SDR coverage and model today? Options: None, 1-5 SDRs, 6-20 SDRs, 20+ SDRs
• What target SDR headcount and timeline would you like deployed? Options: 1-5 in 30 days, 6-15 in 60 days, 16-30 in 90 days, Custom (specify timeline)
• What core responsibilities should SDRs own (select all that apply)? Options: Outbound prospecting, Inbound qualification, Event follow-up, Account-based outreach, Customer expansion support
• Which enablement components do you require (playbooks, call scripts, objection handling, training cadence)? Options: Full training curriculum + onboarding, Playbooks + templates only, Ad-hoc training sessions, No enablement required
• Which CRM, sequencing, and analytics tools will SDRs use (Salesforce, Outreach, HubSpot, other)? Options: Salesforce, HubSpot, Outreach/Sequence tool, Other
• What ramp targets or KPIs should each SDR hit (meetings booked, SQLs, pipeline value) and by when?

Deliver Sales Playbook and Battlecards

• Do you have an existing documented sales playbook today? Options: Yes - comprehensive, Partial / fragmented, No
• Which sales motions should the playbook cover (select all that apply)? Options: New logo acquisition, Expansion / upsell, Renewals / retention, Channel / partner motion
• Do you need competitor battlecards and objection-handling for key competitor profiles? Options: Yes - full set, Yes - top 3 competitors only, No
• What level of deliverable detail do you want (scripts/templates, process frameworks, role-specific checklists)? Options: High (detailed scripts & templates), Medium (frameworks + examples), Light (overview and org-level guidance)
• Would you like workshop sessions to roll out the playbook to sales and SDR teams? Options: Yes - train-the-trainer + sessions, Yes - recorded enablement only, No
• What is your desired timeline to have playbooks and battlecards delivered and in use? Options: 2 weeks, 4 weeks, 6-8 weeks, Custom timeline

Implement Salesforce Pipeline and Dashboards

• Are you currently using Salesforce as your primary CRM? Options: Yes - primary CRM, Yes - limited use, No
• Do you need pipeline stage mapping and standardization across regions or motions? Options: Yes - full mapping, Partial mapping, No
• Which dashboards and KPIs must be available (select all that apply)? Options: ARR / Bookings, Pipeline coverage, Conversion rates by stage, Sales velocity / funnel metrics, Custom KPIs
• Will implementing dashboards require custom objects or third-party integrations? Options: Yes - custom objects, Yes - integrations, No
• Do you require role-based dashboards and access controls for managers vs. reps? Options: Yes, No
• Does your data need cleansing, deduplication, or migration before dashboarding? Options: Yes - significant cleanup, Yes - minor cleanup, No

Build Investor-Ready Financial Model and Cap Table

• Do you have a current 3-5 year financial model and scenario outputs? Options: Yes - detailed model, Yes - high-level model, No
• How is your cap table maintained today? Options: Carta / e-cap table tool, Managed in spreadsheet, Not maintained / incomplete
• Which model outputs do you require (select all that apply)? Options: 3-statement model, Unit economics & LTV/CAC, Scenario / fundraising dilution analysis, Valuation / DCF
• Do you need investor-ready packaging (assumptions write-up, sensitivity cases, audit-ready backup)? Options: Yes - full packaging, Yes - partial, No
• What is your target timeline to receive the finished model and updated cap table? Options: 1 week, 2 weeks, 3-4 weeks
• Are there complex equity instruments (options pools, warrants, convertible notes) that need to be modeled? Options: Yes - detailed list available, No

Manage Investor Roadshow and Pitch Deck Delivery

• Are you planning an active fundraising roadshow tied to this round? Options: Yes - active, Planned, No
• What investor types and geographies are you targeting (growth VC, crossover, strategic, PE)? Options: Growth VCs, Crossover funds, Strategic / corporate, Private equity, Other
• Do you have a current pitch deck and supporting investor materials? Options: Yes - investor-ready deck, Draft deck, No - need creation
• Do you need hands-on support with investor scheduling, introductions, and follow-up tracking? Options: Yes - full support, Yes - partial support, No
• What timeline do you have for running investor meetings and closing commitments? Options: 2-4 weeks, 1-2 months, Flexible
• Would you like the firm to produce an investor Q&A and one-pager tailored to key investor segments? Options: Yes, No

Run M&A Process and Buyer Outreach

• Are you considering a partial or full M&A process as an outcome? Options: Yes - actively pursuing sale, Exploring options, No
• Which buyer types are relevant targets for outreach? Options: Strategic acquirers, Private equity / growth equity, Competitors, Financial buyers / family offices
• Do you have a confidential information memorandum (CIM) or data room content prepared? Options: Yes - ready, In progress, No - need preparation
• What is your preferred deal outcome and timeline (e.g., majority sale, minority recapitalization, timeline to close)? Options: Sell majority / full exit, Minority recapitalization, Strategic partnership / asset sale, Undecided
• Do you need the firm to manage NDA distribution, buyer screening, outreach, and initial negotiations? Options: Yes - full process management, Yes - buyer outreach only, No - advisory only
• Will you require introductions to legal or financial advisors for deal execution? Options: Yes - need introductions, No - have counsel

• Binding Term Sheet / Letter of Intent
• Stock Purchase / Subscription Agreement
• Investor Rights Agreement
• Board Seat & Governance Agreement
• Valuation & Cap Table Confirmation
• Key Covenants & Protective Provisions
• Reps, Warranties & Indemnification Schedule
• Conditions Precedent & Closing Checklist
• Statement of Work (Post-Investment Support)
• Funding Instructions & Escrow Agreement
• Legal & Financial Diligence Deliverables
• Employment, Equity & Retention Agreements
• Tax & Regulatory Forms
• Third‑Party Consents & Approvals Tracker

• Monthly Growth Review
• Quarterly Board Meeting
• Talent & GTM Sync
• Capital Planning & Follow-on Strategy
• Strategic Options & M&A Workshop

• Assign ownership for investor outreach, data room prep, and investor materials.
• Talent lead to proceed with offer letters for board-approved executive hires and report progress at the next growth review.
• Hiring funnel & priority roles
• Agree on next-hire priorities and required timelines to achieve growth targets.
• Define clear ramp and success metrics for new GTM hires and who will own onboarding.
• Identify contingency staffing options to avoid execution gaps.
• Open requisitions for approved roles and share candidate shortlists within 5 business days.
• Create a 30/60/90 onboarding plan for each new GTM hire and circulate to hiring managers.
• Talent team to run two executive reference checks and present hiring offers for board-signoff roles.
• Current cap table & runway review
• Select a preferred fundraising scenario and target raise size and timing.
• Agree on concrete milestones that will unlock a follow-on investment or position the company for growth equity.
• Pre-read confirmation
• Finance to deliver a three-scenario model (base/best/downside) with dilution outcomes and sensitivity analysis.
• Prepare investor-ready materials (updated pitch deck, 12-month plan, data room checklist) within two weeks.
• Set a soft timeline and outreach list for potential co-investors and announce next steps to the board.
• Framing: why explore strategic options now
• Reach consensus on whether to pursue M&A/partnership outreach or continue focusing on organic follow-on growth.
• Produce a prioritized list of targets/buyers and a defensible valuation range for initial outreach.
• Authorize a process and assign advisors/owners to execute the selected path.
• Build and circulate a prioritized buyer/partner list with rationale and contact owners.
• Engage an M&A advisor or prepare an internal outreach pack depending on chosen path.
• Prepare a one-page data summary and teaser for approved outreach and schedule initial exploratory calls.
• Ensure all stakeholders have a single, objective view of current growth performance.
• Identify and assign owners to the top 3 risks impacting the quarter.
• Prioritize and approve any immediate talent or GTM actions required to hit targets.
• Update forecast based on agreed mitigation plans and circulate revised numbers within 48 hours.
• Assign owners and deadlines for each top risk and publish a one-page remediation tracker.
• Talent team to surface candidate slate for any approved urgent hires within 7 days.
• Opening & objectives
• Approve the strategic plan and resource allocation for the coming quarter.
• Decide on any required follow-on capital posture or authorize initiation of a fundraising process.
• Authorize major hires or investments requiring board approval and assign oversight.
• Ensure clear governance outcomes and a tracked action register with owners.
• Finalize and distribute the approved quarterly budget and KPIs within 3 business days.
• If approved, instruct finance to begin follow-on capital preparations and draft investor outreach materials.
• KPI dashboard deep-dive
• Value drivers and target buyer/partner map
• Scenario modeling (best / base / downside)
• Sales productivity and ramp plans
• CEO state of the business
• Follow-on check sizing & investor strategy
• Preliminary valuation comps and ranges
• Financial review & forecast
• International expansion staffing needs
• Top 3 risks and mitigation plans
• Milestones to trigger next round or exit
• Onboarding & enablement checklist
• Process options and timeline
• Strategic priorities: product, GTM, international
• Tactical resource requests (talent / GTM)
• Decisions & timeline
• Decisions, owners, and next steps
• Key decisions: hiring, capital, M&A posture
• Risks & contingency hires
• Decision & next steps (diligence plan or outreach)
• Executive session (investors only)
• Board resolutions & action register