A Quick Check-In: Where We Are and Why We're Talking

• What type of equity raise are you exploring right now? Options: Late-stage private round (pre-IPO), IPO preparation, Secondary offering (public), Convertible note / hybrid, Restructuring / recapitalization, Other
• What's the immediate business driver for this raise—growth plan, acquisition, debt reduction, or something else? Options: Growth / expansion, Acquisition currency, Balance sheet repair / deleveraging, Liquidity for founders / employees, Regulatory / strategic requirement, Other
• How quickly do you need a firm commitment (close) if the process goes smoothly? Options: Immediately / within 30 days, 1–3 months, 3–6 months, 6–12 months, Flexible / no fixed date
• Who will be the final decision‑maker on selecting the lead bookrunner and approving terms? Options: CEO, CFO, Board / lead director, Combined CEO + Board, Special committee, Other
• Tell us briefly about the last time you raised capital—what worked, what didn’t, and how that experience still shapes you?

Who’s Going to Say Whether This Was a Win?

• If you succeed on this raise, who at the company (and outside it) will say “we nailed it” — and what will they point to?
• Rank the priority of the following stakeholders when it comes to defining a ‘good outcome’: CEO, CFO, Board, Legal/Counsel, Major existing investors. Options: CEO highest, CFO highest, Board highest, Legal/Counsel highest, Existing investors highest, Stakeholders are aligned
• What timeline and confidentiality expectations do these stakeholders insist on (e.g., stealth process, limited disclosure, or full marketing)? Options: Strict confidentiality / stealth, Confidential information memorandum to select investors, Broad targeted roadshow, Public pre-announcement required, Other
• Are there board or governance outcomes that would be considered unacceptable even at a higher price (e.g., new veto rights, board seats for investors)? Options: No board changes allowed, One neutral observer only, Willing to negotiate board seat, Depends on investor reputation, Open to governance change for the right partner
• Who do you expect us to call for references before you hire us (which CEO/CFO peers or investors)? Options: 3 CEOs from past 18 months, CFOs from comparable deals, Investors who participated in past deals, Board members / lead directors, We’ll request a full list

If You Told the Market Your Target Price, Would They Laugh?

• What headline valuation are you targeting, and what is the minimally acceptable valuation you would take?
• How did you derive that valuation expectation—forecast multiples, precedent transactions, recent investor conversations, or internal targets? Options: Financial model / forecast, Sector comps / precedent deals, Recent term sheets from investors, Board consensus, Founder aspiration, Other
• If the initial feedback indicates your valuation is optimistic, which of these would you be willing to trade (pick all that apply)? Options: Delay timing, Accept slightly lower valuation, Increase dilution, Add preferred terms for investors, Bring in a strategic investor willing to pay more, Seek a smaller round
• How comfortable are you with a pricing range being published during the bookbuild (i.e., mid-point guidance vs. tight collar)? Options: Tight collar / fixed price only, Mid-point guidance acceptable, Open to wider range, Prefer to keep price confidential until final
• What would make you walk away from market interest even if the headline valuation looked attractive?

Who Do You Want on the Cap Table — and Who Can’t Be There?

• If you could pick three ideal investor profiles to land on the cap table, what would they be (type, reputation, check size, time horizon)?
• Which investor types are absolute no‑gos (e.g., activist funds, short-term trading hedge funds, sovereigns with conflicting interests)? Options: Activist funds, Short-term hedge funds, Competitor / strategic misfit, Retail-led investors, Foundational family office with control intent, None — open to all
• What minimum attributes do you require to consider an investor ‘high quality’ (choose all that apply)? Options: Track record in sector, Typical check size ≥ X, Board experience, Long-term hold mentality, Ability to lead or co-lead syndicate, Provides customer or strategic value
• How important is following-on support from new investors for future financings or IPO readiness? Options: Critical, Important but not only factor, Somewhat important, Not important
• What ownership concentration or single-investor cap would make you uncomfortable post-close? Options: No single investor >10%, No single investor >15%, No single investor >20%, Willing to consider larger stakes for strategic lead, No fixed cap — case-by-case

What Will Make You Sleep Well the Night After Close?

• Describe 3 measurable success signals we should optimize for (price, investor list, timing, governance terms, secondary liquidity, etc.).
• Which of these is the single most important success metric for this process? Options: Peak valuation achieved, Syndicate quality (top-tier funds), Close by a target date, Minimal governance / protective provisions, Sufficient funding to execute strategy, Clean legal terms for future IPO
• How would you weight near-term transactional signals (price, oversubscription) versus longer-term strategic signals (anchor investors, follow-on support)? Options: Price > Strategy, Strategy > Price, Equal weighting, Depends on market conditions
• What would an acceptable post-close board and reporting cadence look like (e.g., board seat for lead investor, quarterly deep dives)? Options: No new board seats, Observer seat only, One board seat for lead, Enhanced reporting but no seat, Open to multiple seats for strategic investors
• Which short-term and long-term KPIs must move following the raise to validate we picked the right partners?

What Changes After Close Should Make You Nervous?

• If new investors start pushing for operational changes post-close, which areas would you be most defensive about (hiring, M&A, pricing, product roadmap)? Options: Hiring / management changes, M&A strategy, Pricing strategy, Product roadmap / R&D, Capital allocation, Other
• How prepared is your management team to present a 90‑day plan to new investors after close? Options: Fully prepared, Need light prep, Need substantial work, Not prepared / will need support
• What cap table or governance cleanups must happen before marketing to avoid distracting diligence issues? Options: Option pool clarity, Outstanding convertible terms cleaned, Founder vesting clarified, Noisy shareholder disputes, All of the above, None
• How do you want us to handle investor requests for seat(s) or board observers during negotiation? Options: Firm no change without Board approval, Open to observer only, Negotiate seat for top-tier only, Case-by-case with pre-approved limits
• What internal communications should be ready pre-close to reassure employees and major stakeholders? Options: Management presentation for staff, FAQ and talking points, Board briefing pack, Customer/partner outreach plan, No pre-close communications

Process Boundaries: What Are You Not Willing to Compromise On?

• Which non-negotiables must the engagement and process respect (retainer/exclusivity, timeline, reference checks, confidentiality)? Options: No exclusivity, Short exclusivity acceptable, Referrals required before engagement, Transparent fee structure only, Strict confidentiality, Other
• How many bank pitches and competing proposals do you expect to evaluate before choosing a lead bookrunner? Options: 1 (one-stop), 2, 3, 3–4, Open to more
• Which engagement terms would make you immediately pause or walk away (e.g., disproportionate retainer, long exclusivity, unclear success fees)?
• How important are third‑party reference checks (CEOs we’ve raised with in last 12–18 months) to you in selecting an adviser? Options: Critical — must speak to at least 3, Important — 1–2 references ok, Nice to have but not decisive, Not necessary
• What reporting cadence and decision gates do you want during the process (weekly check-ins, approval for investor outreach, term sheet review window)? Options: Weekly executive sync, Twice-weekly updates during roadshow, Daily during peak bookbuild, Ad-hoc as needed, Board approvals at key gates

Three Scenarios: Best, Likely, and ‘Fix This’

• Paint your best-case scenario for this process—what happens, who participates, and where you finish on valuation and governance?
• Now the most likely scenario—what’s happening differently than the best case and why?
• If the market shifts and things go wrong, what pre‑agreed triggers should prompt us to pause, reset valuation expectations, or pursue alternative financing (e.g., bridge, smaller strategic raise)? Options: Pause and re-price, Seek bridge financing, Shift to strategic investor talks, Abort and retry later, Other
• Who within your team has final authority to accept a term sheet under time pressure (name and role)?
• What contingency resources (law firms, external CFO advisors, existing investors willing to backstop) should we line up before launching? Options: Outside counsel (name), External CFO/advisor, Anchor existing investor support, Bridge financing provider, None / rely on internal team

• Pre-Workshop Data & Alignment
• Equity Story Workshop — Narrative & Positioning
• KPI & Financial Sensitivity Session
• Investor Criteria & Comparable Mapping
• Mock Investor Panel — Roleplay & Validation

• A documented investor fit heatmap identifying likely supporters and expected objections.
• Ownership and deadlines for drafting materials that prove the narrative.
• Advisory team to draft CIM narrative and a one-page headline summary with three proof points.
• Finance to produce KPI charts (source data) that directly support each proof point.
• Legal and management to confirm any governance or disclosure constraints affecting messaging.
• Advisory team to document the valuation anchor, assumptions, and comparable support.
• Model Walkthrough & Assumptions
• Identify the top 3 KPI drivers that most affect valuation and investor decision-making.
• Quantify a defensible valuation range under base, upside, and downside scenarios.
• Produce a KPI scorecard template to be used in all investor meetings.
• Finance to run and circulate sensitivity tables and charts for the top drivers.
• Prepare a one-page KPI scorecard and backup slides for downside questions.
• Advisory team to craft talking points that translate scenario results into investor-facing language.
• Present Comparable Transactions & Benchmarks
• A ranked, fund-by-fund target list that aligns with the narrative and valuation.
• Opening & Objectives
• Clear outreach plan and thresholds for first-wave meetings.
• Advisory team to produce the fund-by-fund deployment map and finalize the top-20 target list.
• Schedule reference calls with 2–3 CEOs who dealt with each lead banker for top-tier investor validation.
• Prepare investor-specific 1-pagers tying proof points to each target's decision criteria.
• Setup & Roles
• Surface and document all major investor objections and evidence gaps.
• Validate that the narrative and proof points create investor conviction or identify required fixes.
• Produce a finalized FAQ and objection-handling playbook for roadshow use.
• Revise presentation and append backup slides addressing the panel's evidence requests.
• Create the roadshow FAQ/objection playbook with exact phrasing for responses.
• Schedule final rehearsal and approval call with the managing director ahead of roadshow kickoff.
• A single, explicit current-state sentence agreed by management and banker.
• Quantified consequences articulated in monetary and timeline terms.
• A clear future-state outcome statement that defines success for messaging.
• All required materials identified and owners assigned for pre-work.
• Management to deliver a one-page current-state summary and the executive one-sentence statement.
• Finance to circulate the latest model, KPI pack, and 3-year forecasts.
• Advisory team to compile initial comps and a draft investor criteria briefing.
• Schedule core Equity Story Workshop and Mock Investor Panel with confirmed attendees.
• Recap Current State & Consequence
• A validated headline equity narrative that directly references specific KPIs as proof.
• A defensible valuation anchor and a documented acceptable valuation range.
• Clear red lines and fallback positions for negotiations.
• One-Sentence Current State
• Investor Decision Criteria Review
• Map KPIs to Valuation Drivers
• Present Draft Headline Narrative
• 10-Minute Headline Pitch
• Investor Panel Q&A (Real-Time)
• Fit Heatmap: Narrative vs Investor Criteria
• Sensitivity Analysis: Top 3 Drivers
• Map Narrative to KPIs (Proof Points)
• Consequence Quantification
• Stress & Downside Scenarios
• Valuation Anchor & Range
• Future-State Outcome Statement
• Tiering & Outreach Plan
• Critique & Evidence Test
• Objection Handling & Concession Mapping
• Messaging Implications
• Materials Review & Gaps
• Investor Reaction Scenarios
• Confirm Target List & Reference Checks
• Agreement on Headline Message & Proof

• Prepare Confidential Information Memorandum
• Draft Management Presentation Deck
• Produce Fund-by-Fund Deployment Map
• Set Up Virtual Data Room and Populate Documents
• Conduct Investor Roadshow Presentations
• Manage Book-Building and Order Capture
• Lead Term Sheet Negotiation with Investors
• Draft and Finalize Subscription Agreements
• Build Pricing and Allocation Scenarios
• Update Capitalization Table and Pro-Forma Models
• Execute Closing and Funds Flow Instructions
• Draft Public Offering Prospectus
• Secure Investor Commitments and Signatures

Prepare Confidential Information Memorandum

• Do you require a full-length CIM for investor distribution? Options: Yes, No
• What confidentiality protocol should apply to the CIM? Options: NDA required before access, Watermarked distribution with vetting, Summary / teaser only, No restriction (rare)
• Which investor audiences must the CIM address? Options: Institutional growth funds, Strategic acquirers, Crossover investors, Family offices / private investors, Other
• What financial periods and KPIs must be included in the CIM (e.g., LTM revenue, ARR, gross margin)?
• Do you have base documents to build the CIM (e.g., financial model, audited statements, prior investor decks)? Options: Full draft CIM available, Partial materials / slides, Raw financials only, No materials prepared
• What acceptance criteria will confirm the CIM is ready for distribution? Options: CEO approval, CFO approval, Board sign-off, External counsel clearance

Draft Management Presentation Deck

• Is a tailored management presentation required for investor meetings? Options: Yes - full deck, Yes - concise 10-12 slide deck, No - use CIM only
• What presentation tone/level is preferred (investor type orientation)? Options: Growth narrative / market opportunity, Financial deep-dive / metrics, Product demo + GTM focus, Mixed investor audiences
• Who from management will present and who needs prep sessions? Options: CEO, CFO, Head of Sales/GM, No management participation required
• Do you have brand/design templates to apply to the deck? Options: Yes - company template, No - bank template OK, Require bespoke design
• What specific slides must be included (e.g., use cases, unit economics, customer references)?
• What are the approval and sign-off steps for the final deck? Options: CEO sign-off, CFO review, Board review, Legal review required

Produce Fund-by-Fund Deployment Map

• Do you require a fund-by-fund deployment map (list of specific active funds and likely ticket sizes)? Options: Yes - detailed fund-by-fund, Yes - top 50 funds, No - sector-level targeting only
• Which fund typologies should be included? Options: Growth equity funds, Crossover / crossover-public funds, Strategic / corporate VCs, Family offices, Sovereign / pension funds
• What level of data do you expect for each fund (AUM, recent deployments, sector focus, partner contact)? Options: Full profile (AUM, recent deals, partner names), Basic profile (AUM & sector), Minimal (name + likelihood)
• Are there known investor preferences or exclusions we must respect (e.g., embargoed investors, prior conflicts)? Options: Yes - list provided, No
• What timeline do you expect for delivery of the deployment map? Options: 48-72 hours, One week, Two+ weeks
• What will be the acceptance criteria for the map (e.g., top X qualified investors identified and contactable)?

Set Up Virtual Data Room and Populate Documents

• Do you require a VDR to be set up and populated? Options: Yes - set up and populate, Yes - set up only, we populate, No - not required
• Which VDR provider or security features do you prefer? Options: Intralinks, Firmex, Box/Google/OneDrive with enhanced controls, Other / bank recommended
• What categories of documents will be uploaded (financials, cap table, contracts, IP, customer references)? Options: Financial statements, Cap table & charter documents, Material contracts, IP and tech docs, Customer references / case studies
• Are there documents requiring redaction or external counsel review before upload? Options: Yes - legal redaction required, No - safe to upload
• What access controls and expiration policies do you require for investor access? Options: Time-limited access, Watermarked viewing only, Download disabled, Tiered access by investor
• Who will own data room administration and user management? Options: Bank to administer, Company to administer, Shared administration

Conduct Investor Roadshow Presentations

• Do you plan an investor roadshow (number of meetings and duration)? Options: Yes - 20+ meetings over 2-3 weeks, Yes - 10-20 meetings, Targeted 5-10 meetings, No broad roadshow, targeted outreach only
• Will roadshow meetings be virtual, in-person, or hybrid? Options: Virtual only, In-person only, Hybrid (both)
• Who from management will present and what prep time is required? Options: CEO & CFO, CEO only, CFO & Head of Strategy, Board member involvement
• Do you require scheduling and travel logistics support? Options: Full scheduling & travel management, Scheduling only, We handle logistics
• What are your target investor outcomes from the roadshow (e.g., indications of interest, term sheets, strategic discussions)? Options: Soft IOIs / indications, Firm IOIs / commitments, Term sheet submission, Strategic partnership talks
• What are the acceptance criteria for successful roadshow execution (e.g., X qualified IOIs, Y lead indications)?

Manage Book-Building and Order Capture

• Do you want the bank to manage book-building and capture orders? Options: Yes - full book-building, Yes - capture only, we manage allocation, No - advisory only
• What is the desired book-building period (days)? Options: 1-3 days, 4-7 days, 8-14 days, Flexible / market-driven
• How should orders be prioritized during allocation (price first, long-term investor quality, strategic fit)? Options: Price priority, Investor quality & fit, Pro-rata vs first-come, Custom allocation policy
• Do you require live order capture tooling integrated with CRM? Options: Yes - integrate with CRM, Yes - bank system only, No preference
• Are there investor order types to support (conditional orders, AMM, laddering)? Options: Conditional orders, Indicative only, Firm commitments, Other
• What are the acceptance criteria for a successful book (e.g., subscribed X% at target price, Y quality investors)?

Lead Term Sheet Negotiation with Investors

• Should the bank lead negotiation of term sheets on the company's behalf? Options: Yes - lead and negotiate, Yes - advise but company leads, No - internal counsel handles negotiations
• Which commercial terms are highest priority to negotiate? Options: Price / valuation, Board composition & rights, Protective provisions, Registration rights / lock-ups, Other
• Who has final authority to accept negotiated terms (role/individual)? Options: CEO, CFO, Board/Chair, Special committee
• Will external counsel be engaged to review term sheets and negotiate legal language? Options: Yes - company counsel, Yes - bank counsel, No - internal legal team
• Are parallel negotiations with multiple lead investors acceptable? Options: Yes - run competitive process, No - single lead preferred, Case-by-case
• What are the acceptance criteria for a negotiated term sheet (e.g., valuation threshold, investor quality checklist)?

Draft and Finalize Subscription Agreements

• Do you need bank support to draft and finalize subscription agreements? Options: Yes - draft & negotiate, Yes - review & advise, No - counsel to handle
• Which jurisdiction and governing law should the subscription agreements follow? Options: Delaware, England & Wales, Local jurisdiction (specify), Other
• Do you have template agreements to use or should new templates be drafted? Options: Use company templates, Use investor templates, Draft new templates
• Are there bespoke clauses likely required (custom liquidation preferences, transfer restrictions, anti-dilution)? Options: Yes - list to be provided, No - standard clauses only
• What signing mechanism is preferred for subscriptions (e-signature, wet ink, escrow)? Options: E-signature, Wet ink, Escrow agent
• What are the approval steps and turnaround expectations for finalizing subscription agreements? Options: 48-72 hours, One week, Custom / negotiable

Build Pricing and Allocation Scenarios

• Do you require modeled pricing and allocation scenarios prior to final pricing? Options: Yes - multiple scenarios (base, upside, downside), Yes - single scenario, No
• What valuation range and reference points should be modeled? Options: Management target range, Comparable transactions, Precedent public comps, Hybrid
• Which allocation policies should be evaluated in scenarios? Options: Pro-rata allocation, Strategic investor priority, Anchor investor allocation, Equal treatment
• What sensitivity analyses are required (price, demand, oversubscription levels)? Options: Price sensitivity, Subscription level scenarios, Investor mix impact, Dilution impact
• Do you require pre-approval thresholds for moving between scenario outcomes (e.g., minimum price or investor quality)? Options: Yes - define thresholds, No - final decision ad hoc
• What are the acceptance criteria for selecting a pricing/allocation scenario?

Update Capitalization Table and Pro-Forma Models

• Do you require the cap table and pro-forma models to be updated for the transaction? Options: Yes - full pro-forma for multiple scenarios, Yes - single post-close cap table, No - company will update
• What convertible instruments and option pools must be modeled? Options: Existing options & RSUs, Convertible notes / SAFEs, Warrants, None
• Do you have a canonical cap table file and model template to use? Options: Yes - provide master file, Partial data only, No - start from scratch
• Should post-transaction governance changes (board seats, veto rights) be reflected in the pro-forma? Options: Yes - include governance outcomes, No - financial only
• What level of detail is required for investor-facing pro-formas (share class breakdown, dilution waterfall)? Options: Detailed waterfall & share classes, High-level summary only
• What are the acceptance criteria for the updated cap table/pro-forma?

• Engagement Letter / Advisory Agreement
• Statement of Work (SOW)
• Fee Schedule & Payment Terms
• Retainer Authorization & Deposit
• Exclusivity & Engagement Boundaries
• References Release & Check Consent
• Legal Attachments & Module Registry
• Conflict of Interest Disclosure
• KYC/AML & Compliance Questionnaire
• Wire Instructions & Payment Setup
• Termination & Refund Terms
• Final Signature & Authorization

• Post-Close Results Review
• Cap Table & Governance Transition
• Investor Onboarding & Relationship Management
• Performance Monitoring & Success Signal Cadence
• Post‑Mortem & Continuous Improvement (Readiness for Next Round)

• Build the agreed dashboard with live data feeds and circulate a link to stakeholders within 10 business days.
• Finance to update internal cap table model and publish an 'owner of record' report to stakeholders.
• HR to schedule employee communications regarding option pool changes within 5 business days.
• Current Onboarding Status & One‑Sentence Summary
• Confirm all subscription and onboarding tasks are complete or have owners with deadlines.
• Align investor reporting cadence, content, and primary contacts.
• Establish escalation protocols and point people for investor issues.
• Send standardized welcome packet and reporting calendar to all investors within 3 business days.
• Finalize and distribute the first investor update template; assign IR lead responsible for distribution.
• Log any outstanding onboarding items and assign owners with 48-hour deadlines.
• Compile list of investors willing to serve as references and note any confidentiality restrictions.
• One‑Sentence Future State & Why It Matters
• Finalize a measurable KPI set tied to the success signals and assign clear owners.
• Approve the dashboard/reporting template that proves the future state and enables rapid validation.
• Agree on escalation thresholds and the cadence for recurring performance reviews.
• Objective & One‑Sentence Current State
• Assign metric owners and publish a RACI for monthly reporting and quarterly reviews.
• Draft an escalation playbook describing triggers, contacts, and communications templates.
• Schedule recurring calendar invites for the agreed review cadence and circulate pre-read deadlines.
• One‑Sentence Retrospective Framing
• Document and prioritize lessons learned with measurable evidence and owners.
• Update the fundraising playbook with specific process changes and tools to reduce future risk.
• Agree on a readiness timeline and who will own pre-emptive actions for the next capital raise.
• Produce a Lessons Learned Report with prioritized playbook updates and circulate within 7 business days.
• Update CIM and roadshow templates per agreed changes and store in the central deal playbook.
• Create a 'Next Raise Readiness' project plan with milestones and owners to be revisited quarterly.
• Schedule a 90‑day check to validate that implemented improvements are working as intended.
• Ensure leadership shares a single, precise understanding of what closed and why.
• Identify material gaps against success signals and approve immediate remediation where required.
• Assign owners and deadlines for any urgent filings, investor notifications, or remediation tasks.
• Prepare a one‑page Closing Variance Report and distribute to CEO/CFO/board within 24 hours.
• If governance triggers were hit, instruct counsel to draft required notices and board resolutions.
• Notify transfer agent and registrar of allocations requiring same‑day processing.
• One‑Sentence Current Cap Table State
• Validate the accuracy of the post‑close cap table and confirm transfer agent instructions.
• Finalize and authorize governance changes (board seats, consents, resolutions).
• Agree on filings and compliance milestones with owners and deadlines.
• Direct transfer agent to update ledger and issue share certificates as applicable.
• Counsel to prepare and circulate signed board resolutions and investor rights agreements for execution.
• One‑Sentence Consequence & Future State
• Subscription Docs & KYC/AML Completion
• Cap Table Walkthrough (Line-by-Line)
• What Went Well (Evidence)
• Confirm Metrics & Success Signals
• Legal & Compliance Checklist
• Closing Outcomes Summary
• Investor Profiles & Engagement Preferences
• Dashboard & Reporting Template Review (Proof)
• What Surprised or Failed (Root Causes)
• Board Composition & Governance Actions
• Data Sources, Frequency & Owners
• Success Signal Dashboard: Actual vs Target
• Reporting Calendar & Template Review
• Process & Playbook Improvements
• Escalation Triggers & Response Playbook
• Reference Requests, Quiet Periods, and PR Coordination
• Drivers of Variance & Impacts
• Readiness Checklist & Timeline for Next Financing
• Employee Equity & Option Plan Adjustments
• Immediate Risk Assessment & Mitigation Options