Quick orientation, and why now

• Tell me the immediate reason you are starting a fundraise now Options: Runway below 12 months, Valuation inflection or growth acceleration, Competitive threat requiring capital, Planned acquisition or strategic opportunity, Investor-driven timeline, Other
• Describe your target round size and preferred timing, including whether you expect a single close or tranches
• Which stakeholders must approve this financing and what does each care about most Options: Founder-CEO, Board, CFO/Finance, CRO/GTM leader, Existing lead investor, Independent director, Other
• Estimate how many months of runway you have at current burn Options: <6 months, 6-9 months, 9-12 months, 12-18 months, >18 months
• Walk me through your last funding round, the valuation then, and how that shapes expectations today
• If you miss your target timeline and runway falls below 9 months, what is the single operational consequence that forces a different path

Where the numbers will help or hurt your case

• Which single KPI, if exposed as weaker than projected during diligence, would cause investors to step back Options: ARR growth, Net dollar retention, Gross margin, CAC payback, Revenue recognition clarity, Other
• Walk me through your ARR growth, net dollar retention, and topline seasonality over the past 12 months
• Estimate your current gross margin and burn multiple using the ranges below Options: Gross margin <40% / Burn multiple >3, Gross margin 40-60% / Burn multiple 2-3, Gross margin 60-75% / Burn multiple 1-2, Gross margin >75% / Burn multiple <1, Not sure / needs model
• Tell me about any recent restatements, revenue recognition complexities, or one-off adjustments in your financials
• Who owns the financial model and can update scenarios within 48 hours during outreach Options: Internal finance lead, Interim CFO, External financial advisor, Shared responsibility across finance and CEO, Other
• If investors require audited statements within six weeks, can you provide them without delaying the process Options: Yes, audited available, No, need 6+ weeks, Partial, would delay the timeline, Not applicable

How decisions actually get made inside your company

• When valuation and control trade off, who typically breaks the tie and on what basis
• List the decision makers, their decision criteria, and how quickly each can sign off
• Describe any prior board or investor dynamics that slowed a financing and what changed to resolve it
• Who will be the single point of contact for investor negotiations and what authority do they have Options: CEO, CFO, General counsel, External advisor, Board chair, Other
• Would you proceed with the process or pause if a board member refuses the proposed governance guardrails Options: Proceed, Pause and rework terms, Seek alternative investors, Require full board vote first

How ready is your pitch and the evidence behind it

• Identify the three strongest pieces of evidence for your growth thesis you would present tomorrow
• Outline the five core slides in your deck and the data sources that prove each claim
• List the KPIs your targeted investors track and where you sit relative to typical thresholds Options: ARR growth, Net dollar retention, Gross margin, Gross churn, Expansion revenue, CAC payback, Other
• Do you have a populated data room with the last 24 months of financials, cap table, customer contracts, board minutes, and key vendor agreements Options: Last 24 months financials, Cap table and option pool, Customer contracts and SLAs, Top customers NDR and logos, Board minutes, Employee equity agreements, Legal opinions, None of the above, Other
• How many external customer or partner references can speak to growth and retention in the next two weeks Options: 0, 1-2, 3-5, 6+
• Do you already have a remediation plan for a material revenue recognition issue that would preserve the closing timeline Options: Yes, plan in place, Partial plan, needs work, No plan, Unsure

The risks that could stop this in its tracks

• Name the single risk that would make you cancel the fundraise today
• Catalog legal, customer, or product issues that could appear during diligence and estimate time to resolution for each
• How would a 5 percentage point rise in churn over the next two quarters change your valuation expectation
• Have any investors already flagged concerns in early conversations, and if so what were they Options: Yes, specific concerns noted, Yes, general hesitation, No concerns yet, Unsure
• Identify any contingency or bridge capital options that are available if the round delays Options: Internal cash reserves, Existing investors offering bridge, Convertible notes, Debt facility, No contingency available, Other
• Point to a due diligence finding that would make you stop the process rather than renegotiate terms

The other paths on the table

• State the alternative you are closest to choosing right now and why Options: Continue with internal outreach, Hire a boutique advisor, Work with an investment bank, Let existing investors lead, Pursue a strategic lead investor, Other
• Catalog the external providers or internal approaches you have evaluated so far
• For each option you could keep, what would have to be true about its performance or cost for you to stick with it
• Has anyone internally proposed solving fundraising without an outside advisor, and who made that case Options: Yes - CEO, Yes - CFO, Yes - Board member, No one has proposed it, Other
• Rate the probability you will choose each path below Options: Internal DIY, Boutique advisor, Investment bank, Existing investor-led, Strategic investor lead, Other
• Specify a milestone your current approach would need to miss for you to decide to engage an external advisor immediately

Can your team move at investor speed

• Name the documents you could not assemble within 10 days if investors requested a full diligence package
• Provide the list of third-party systems that must connect to support investor requests, for example payroll, billing, or analytics Options: Payroll, Billing/subscription platform, CRM, Analytics warehouse, Identity provider, Other
• Can you assign a dedicated internal lead for diligence and outreach who can commit to at least a 20 percent time allocation Options: Yes - assigned, Yes - can assign, No - cannot commit, Unsure
• Provide the role and title of the person who will control access to the data room and handle NDAs and redline negotiation
• Are there regulatory approvals or compliance steps that could gate closing timelines Options: Yes, No, Probably, Unsure
• Would you pause the process or attempt remediation if a core system is not auditable to investor standards Options: Pause process, Attempt remediation while proceeding, Renegotiate timeline, Undecided

Signals that will make us move fast

• Suppose we deliver three competitive term sheets within your timeline, what is the fastest decision you can make and who needs to sign
• Specify the commercial terms you will not compromise on, for example governance or liquidation preferences Options: Board seats, Liquidation preference, Anti-dilution protection, Voting rights, Protective provisions, Other
• State the role and title of the person who will sign the engagement and the timeline they expect
• Can the team commit to start investor outreach within 7 days once the engagement terms are agreed Options: Yes, Maybe with conditions, No
• What specific success signals would make you consider the engagement a win at 30, 60, and 90 days
• Are you prepared to sign a mutual commit within 48 hours if we align on terms and confidentiality Options: Yes, Probably, No

• Narrative Framework Workshop
• KPI Validation and Evidence Workshop
• Pitch Deck Draft Review
• Data Room Readiness and Due Diligence Checklist

• Initiate remediation tasks for high priority missing documents with assigned owners and due dates.
• Produce a KPI data pack including source files, definitions, and calculation workbook for each validated KPI.
• Document and assign any data remediation tasks with completion dates.
• Confirm slide-level outline and flow tied to the narrative
• Slide-level outline ratified and a prioritized edit list created for the next deck draft.
• Owners and deadlines assigned for all slide edits and supporting data pulls.
• Update the pitch deck with prioritized edits and circulate draft 2 by the agreed deadline.
• Prepare concise speaker notes for each investor-facing slide aligned to the narrative and KPIs.
• Review standard data room index by investor type
• Completed data room index with status for each item and a prioritized remediation plan.
• Access and version control rules defined and scheduled for implementation before outreach.
• Upload existing documents to the agreed data room structure and tag each with status.
• Confirm fundraising objectives and target investor profile
• One-paragraph vision statement and three investor-facing value points approved for use in materials.
• One-page narrative document agreed and scheduled for distribution to slide authors and data owners.
• Publish the one-page narrative document to the shared workspace.
• Assign slide authors and data owners by narrative section for follow-up work.
• Confirm investor archetypes and evidence requirements
• Validated KPI list with current values and target thresholds defined for each investor archetype.
• Named data owners and agreed timelines to produce supporting evidence for each KPI.
• Draft the one-paragraph vision and positioning
• Map existing documents to the index and surface gaps or red flags
• Review each slide for core message and supporting evidence
• Present candidate KPI list mapped to narrative points
• Prioritize missing items and assign remediation actions with timelines
• Validate current values, data sources, and variance to targets
• Prioritize edits and create a slide change log with owners and deadlines
• Define three investor value points with supporting evidence
• Produce the one-page narrative document
• Agree access controls and versioning rules for investor sharing
• Agree visual and data presentation rules
• Agree thresholds, evidence packages, and remediation steps

• Fundraise Plan Walkthrough

• Confirm the current state and its cost
• You confirm the stated current state and accept the quantified cost to runway, time, or dilution as accurate.
• Provide the confirmed target raise amount, acceptable dilution range, and top decision-makers with their availability windows.
• You agree that the prioritized investor map addresses the scatter and will reduce total meetings to the target threshold.
• Review the prioritized investor map
• Deliver a prioritized investor map draft including contact tiers and rationale within three business days.
• You confirm the outreach sequence and meeting cadence will produce multiple term sheets within the proposed timeline and that the executive time estimate is acceptable.
• Share the proposed outreach sequence and sample investor cadence, including suggested email touches and meeting formats.
• Walk through the outreach sequence and messaging cadence
• You accept the competitive process mechanics as the route to protect valuation and governance outcomes.
• Confirm meeting cadence and owner responsibilities
• Agree target evidence signals for starting outreach, for example number of prioritized investors committed to initial meetings and the minimum KPI thresholds to support valuation.
• You agree the remaining evidence and deliverables needed before outreach begins.
• Confirm the maximum acceptable total investor meetings before close and the desired timeline for term sheet compression.
• Demonstrate the competitive process mechanics
• Validate alignment with your objectives
• Agree next steps and evidence required to proceed

• Fundraise Plan Walkthrough
• Fundraise Plan Walkthrough Deck
• Fundraise Plan Brief

• meeting
• slides
• document

• Refine financial model and forecast scenarios
• Create investor-ready pitch deck
• Assemble and maintain investor data room
• Produce targeted investor list and prioritization
• Draft outreach teaser and intro messaging
• Run competitive term sheet process
• Lead term sheet negotiation on economics and governance
• Build investor KPI pack and traction dashboard
• Model cap table and dilution scenarios
• Prepare diligence responses and document packages
• Run CEO pitch rehearsals and Q&A prep
• Coordinate closing logistics and funding handoff
• Provide market term sheet benchmarks and comps

Refine financial model and forecast scenarios

• How many months of historical revenue and expense detail can you provide (monthly P&L, cash flow) for model inputs? Options: 12 months, 24 months, 36+ months, Consolidated annual only
• Which revenue streams should be modeled separately (e.g., ARR subscriptions, professional services, marketplace fees)? Options: ARR subscriptions, One-time services, Marketplace transactions, Other - describe
• Who on your team will own answers and provide source files for customer, ARR, and churn assumptions (title or role)?
• Provide the growth and margin scenarios you want stress-tested (base, stretch, downside) and the corresponding timeline (months to model). Options: 3 scenarios (base/stretch/downside), 2 scenarios (base/downside), Custom - describe
• Identify any accounting or recognition items that require special handling in the model (deferred revenue, multi-element ARR, revenue reversals). Options: Deferred revenue, Multi-element ARR, Revenue reversals/credits, Stock-based comp impact, Other

Create investor-ready pitch deck

• Which core deck slides do you need drafted or rebuilt (choose all that apply: problem, solution, traction, unit economics, financials, use of proceeds)? Options: Problem & market, Product & traction, Go-to-market & sales model, Unit economics & CAC payback, Financial projections & use of proceeds
• How many data-driven charts should be prepared for the traction slide (ARR curve, cohort retention, bookings by cohort)? Options: 1-2 charts, 3-4 charts, 5+ charts
• Specify the target deck length and audience format you want (10-min investor intro, 20-min board-ready, one-pager teaser). Options: One-pager teaser, 10-slide investor intro, 15-20 slide detailed review
• Describe any regulatory, clinical, or industry credentials that must be called out on the deck (e.g., HIPAA readiness, SOC 2 type II, FDA designation). Options: HIPAA/PHI readiness, SOC 2 type II, Regulatory filings/clearances, None
• What acceptance criteria will confirm the investor-ready deck is complete (e.g., approved CFO financial slides, slide-level data source list, final design file)?

Assemble and maintain investor data room

• Which data room folder structure do you prefer for diligence (examples: Corporate, Financials, Cap Table, IP, Customers, Legal)? Options: Standard folder set (Corporate/Financials/Legal/Cap Table/IP/Customers), Custom folder set - describe, I need guidance
• How many versions of historical financial statements and supporting schedules will you upload (audited, reviewed, management monthly packs)? Options: Audited + monthly management packs, Reviewed + monthly packs, Management packs only
• Provide the current cap table artifact types you will upload (cap table spreadsheet, option grant ledger, SAFEs/notes list). Options: Cap table spreadsheet, Option grant ledger, List of SAFEs/notes, Other - describe
• Indicate any third-party sensitive documents that require access controls or NDAs before viewing (customer contracts with confidentiality clauses, IP assignment agreements). Options: Customer contracts, IP assignment agreements, Employee personal data, None
• What percentage of the target diligence checklist must be uploaded to mark the data room 'ready' (for example, 80% of required folders populated)? Options: 60%, 75%, 80%, 90%+

Produce targeted investor list and prioritization

• Which investor types should be included in the outreach mix (seed/Series A VCs, growth equity, crossover, strategic corporate investors)? Options: Early-stage VCs, Growth equity, Crossover/late-stage, Strategic corporates
• How many prioritized targets do you want on the initial list and how many backup targets (e.g., 25 primary / 50 total)? Options: 15 primary / 30 total, 25 primary / 50 total, Custom - specify numbers
• Identify any investors you explicitly wish to avoid and the reason (e.g., prior negative interactions, conflicting portfolio companies).
• Provide the geographic focus for investor outreach (US West, US East, Europe, Asia) and any timing preferences tied to regional calendars. Options: US West, US East, Europe, Asia/Pacific, Hybrid
• Which firm fit criteria should be weighted highest when prioritizing (check size, sector specialization, lead reputation, ability to syndicate)? Options: Check size, Sector specialization, Lead reputation, Syndication ability

Draft outreach teaser and intro messaging

• What format should the initial outreach take for your targets (two-line email teaser, one-page PDF teaser, LinkedIn introduction)? Options: Two-line email, One-page PDF teaser, LinkedIn InMail
• Provide the one-sentence positioning you want to lead with (include metric anchor such as 'growing ARR at X% YoY' or 'NDR of Y%').
• Specify the call-to-action you want included in outreach (intro call, request for lead interest, ask for feedback on model). Options: Intro call, Request lead interest, Ask for feedback, Request NDA then materials
• List any compliance or disclosure items that must be present in messaging (e.g., active exclusivity, live term sheet, confidentiality required). Options: Active exclusivity, Live term sheet, Confidentiality required, None
• Which outreach cadence do you prefer for follow-ups (days between touchpoints and max outreach attempts)? Options: 3 touchpoints over 2 weeks, 5 touchpoints over 4 weeks, Custom cadence

Run competitive term sheet process

• Which auction format do you want to run (time-boxed competitive process, rolling lead-first process, single-lead negotiation)? Options: Time-boxed competitive auction, Rolling outreach with preferred lead, Single-lead negotiation
• How long should the active competitive window run from first investor meeting to initial term sheet deadline? Options: 4 weeks, 6 weeks, 8+ weeks
• Identify any deal-level hard constraints that must be enforced during the process (maximum dilution %, minimum valuation, board composition limits).
• Provide the number of parallel meetings you are comfortable committing leadership time to per week during outreach. Options: 1-3 meetings/week, 4-6 meetings/week, 7+ meetings/week
• Indicate the escalation rule if multiple term sheets arrive simultaneously (e.g., run final round with top 3 bidders, accept highest economic terms). Options: Final round with top 3, Accept highest economic terms, Board to select preferred lead

Lead term sheet negotiation on economics and governance

• Which term sheet provisions are highest priority for founder economics (valuation, liquidation preference, anti-dilution protection)? Options: Valuation/pre-money, Liquidation preference, Anti-dilution protection, Board rights
• How should we handle governance changes you want to avoid (e.g., new protective provisions, supermajority vetoes)? Options: Reject any new protective provisions, Negotiate limited carve-outs, Open to discussion
• Who on your side can execute negotiation trade-offs (CEOs level authority, board approval required for changes above threshold)? Options: CEO can sign, Board approval required, Founder + Board committee
• Specify deal economics thresholds that trigger automatic escalation to the board for approval (e.g., dilution >X%, new class rights).
• What negotiation cadence do you prefer for redlines and counterproposals (48 hours turnaround, synchronous redline session, weekly alignment)? Options: 48 hour turnaround, Synchronous redline session, Weekly alignment calls

Build investor KPI pack and traction dashboard

• Which KPIs must appear on the investor pack dashboard (ARR, net dollar retention, churn, gross margin, CAC payback)? Options: ARR, Net dollar retention (NDR), Gross margin, CAC payback, Other - specify
• How frequently should dashboard metrics be updated and shared during the process (weekly, bi-weekly, monthly)? Options: Weekly, Bi-weekly, Monthly
• Provide the primary data sources for KPIs (billing system, CRM bookings, product analytics) and who has access rights. Options: Billing / finance system, CRM, Product analytics, Other
• Indicate any KPI thresholds that would materially change positioning to investors (e.g., NDR below 100%, gross margin under target).
• What visualization formats do you prefer for investor-ready dashboards (time series charts, cohort tables, waterfall charts)? Options: Time series charts, Cohort tables, Waterfall charts, Custom visual

Model cap table and dilution scenarios

• Which cap table artifacts will you provide for modeling (current cap table spreadsheet, option pool schedule, convertible instruments list)? Options: Cap table spreadsheet, Option pool schedule, Convertible notes/SAFEs list, None - need template
• How many transaction scenarios should we model (single close, up-round, down-round, staged closings)? Options: 1-2 scenarios, 3 scenarios, 4+ scenarios
• Describe the treatment you prefer for option pool expansion (pre-money dilution vs post-money allocation). Options: Pre-money expansion, Post-money allocation, Need recommendation
• Specify any planned equity events that must be included in the waterfall (recent grants, planned hires with grants, outstanding conversion triggers).
• Which outputs do you need from the cap table model (dilution schedules, pro forma cap table snapshots, founder ownership waterfall)? Options: Dilution schedule, Pro forma snapshots, Founder waterfall, All of the above

Prepare diligence responses and document packages

• Which diligence areas need templated responses prepared (finance, legal, IP, customer references, security/compliance)? Options: Financial due diligence, Legal & contracts, IP & assignments, Security/compliance, Customer references
• How many customer references and which types of reference materials should be prepared (case studies, reference calls, sanitized metrics)? Options: 1-2 reference customers, 3-5 reference customers, 5+ references
• Provide details of any known diligence red flags that require narrative responses (revenue recognition issues, pending litigation, key person risk).
• Indicate whether you need us to draft standard diligence templates (FAQ, revenue reconciliation memo, cap table explainer) or just compile existing answers. Options: Draft templates, Compile existing answers, Both
• What turnaround time can you commit to for answering investor diligence questions during active outreach? Options: Within 24 hours, Within 48 hours, Within 72 hours

Run CEO pitch rehearsals and Q&A prep

• Which pitch formats should the CEO rehearse (15-minute intro + 15 Q&A, 30-minute detailed review, 10-minute lightning pitch)? Options: 10-minute lightning, 15+Q&A, 30-minute detailed review
• How many rehearsal sessions do you want and what participants should attend (board members, head of sales, CFO)? Options: 1 rehearsal (CEO only), 2-3 rehearsals with leadership, Weekly rehearsals until close
• Identify the toughest audience questions you expect so we can prepare rebuttals (unit economics, churn, competitive displacement, defensibility).
• Provide your preferred feedback method during rehearsals (live coaching, redlines to script, recorded review). Options: Live coaching, Script redlines, Recorded review
• What success signals will confirm the CEO is investor-ready for meetings (consistent 10-15 minute pitch under time, scoring rubric met, mock Q&A passed)?

Coordinate closing logistics and funding handoff

• Which closing documents must be prepared or coordinated (subscription agreement, investor rights agreement, side letters, escrow instructions)? Options: Subscription agreement, Investor rights agreement, Side letters, Escrow/wire instructions
• How will legal work be handled at close (we coordinate with your counsel, we provide template redlines, you supply counsel contact)? Options: We coordinate with your counsel, We provide template redlines, You supply counsel contact
• Provide your wiring and bank instruction readiness and who will be authorized to sign closing documents.
• Indicate any post-close handoff items you want tracked (investor intro plan, board seat onboarding, reporting cadence). Options: Investor intro plan, Board onboarding, Regular reporting cadence, None
• Which timing constraints are critical for close (funding needed by certain date to avoid runway shortfall, key hires dependent on funding)?

• Non-Disclosure Agreement (NDA)
• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Fee and Success-Fee Schedule
• Expense Reimbursement and Disbursement Terms
• Agent Authorization
• Termination and Transition Addendum
• Data Processing Addendum (DPA)

• Close Health Check (weeks 1-4 post-close)
• First Post-Close Measurement (weeks 4-10)
• 90-Day Acceptance Gate (around day 90)
• Post-Close Quarterly Review

• Create and circulate a roster of outstanding investor requests with target resolution dates.
• Produce an updated cash reconciliation and revised runway model reflecting actual receipts and current burn.
• Complete CRM ingestion for remaining investor contacts and confirm executed investor documents are stored.
• Document and publish the remediation plan to reach targets by the 90-day acceptance gate.
• Close any remaining legal or filing items required to finalize governance changes post-transaction.
• Restate acceptance criteria and numeric targets
• Produce a documented acceptance decision that records pass/fail per numeric criterion from Engagement Scope.
• Capture the named signatory for formal acceptance and the verification method for any conditional items.
• If remediation is required, establish a concrete resolution plan with deadlines and verification checkpoints.
• Publish the acceptance decision record showing pass/fail per criterion and the named signatory entry.
• If conditional, open remediation tickets with target resolution dates and verification criteria.
• Quarter cash runway and burn review
• Validate that cash runway and use-of-proceeds pacing remain acceptable against targets recorded in Engagement Scope or document necessary adjustments.
• Ensure milestone completion rate is tracked and investor reporting obligations are scheduled and resourced.
• Maintain a clear backlog of investor requests with deadlines to prevent follow-up drift.
• Update the use-of-proceeds tracker and publish variance notes for any line-item overages.
• Schedule the next investor report and assemble the required financial and milestone materials.
• Re-confirm close checklist and owners
• All material closing deliverables are confirmed complete or have an assigned remediation plan with target dates.
• Investor handoff plan for CRM and intro communications is scheduled and documented.
• Data room archival approach and timeline agreed.
• Publish the closing ledger showing gross and net proceeds, fees deducted, and any pending tranches.
• Finalize cap table updates and circulate a confirmed post-close cap table snapshot.
• Deliver investor onboarding packet and schedule the first investor intro communications.
• Archive the agreed set of data-room documents to the agreed retention location and set read-only access.
• Present net proceeds and cash reconciliation
• Confirm whether net proceeds and runway are tracking to targets recorded in Engagement Scope and document any variances.
• Ensure investor onboarding progress reaches the agreed percentage by the acceptance gate or has a remediation plan.
• Agree a timebound remediation plan for any gaps, with clear deliverables and dates.
• Confirm funds receipt and bank acknowledgements
• Present outcome data against each criterion
• Review post-close runway and spend pacing
• Use-of-proceeds budget vs actuals
• Document pass or fail per criterion
• Investor onboarding status
• Milestone progress and investor reporting cadence
• Cap table and legal filings status
• Investor handoff and CRM transfer plan
• Open investor requests and outstanding action items
• Diagnose gaps and root causes
• Formal acceptance decision and signatory capture
• Agree corrective actions and timeline to acceptance gate
• Data room closure and archival
• Agree remediation items and resolution timeline for any failed or conditional criteria
• Agree next quarter priorities and monitoring checkpoints
• Open issues and immediate remediation actions