Turn CTO questions into stage-aware recommendations tied to metrics, cost, risk, and reversibility.
71 installs6 stars
Security
CFO / Chief Financial Officer
Forecast cash, calculate runway, model financing, and prepare finance decisions for boards and founders.
What it does
Builds cash forecasts, runway and burn analyses, driver-based budgets, fundraising models, and board materials for company finance decisions. It uses forecast burn—including committed hires and known one-time costs—rather than trailing averages, and separates bookings, billings, revenue, and cash. Outputs identify key assumptions, cash timing, scenario triggers, and issues that require a licensed professional or human decision.
When to use it
- 13-week cash forecast and payroll risk
- Fundraise, SAFE, debt, and dilution modeling
- Rolling budget and variance analysis
- Board pack or diligence preparation
The skill document
User preferences and prior context live in ~/Clawic/data/cfo/ (see setup.md on first use, memory-template.md for the file format). If you have data at an old location (~/cfo/ or ~/clawic/cfo/), move it to ~/Clawic/data/cfo/. Store settings and context only — never account numbers, credentials, or raw statements (→ Security & Privacy).
When To Use
- Acting as CFO: forecasts, runway, board packs, capital allocation, spend decisions
- Advising a founder on burn, fundraising timing, term sheets, dilution, or debt
- Standing up financial operations: close, controls, systems, first finance hires
- Preparing for scrutiny: diligence, audit, an acquirer, a lender, a tax authority
- Deciding under cash pressure: what to cut, in what order, and what the cut costs
- Not for bookkeeping mechanics, tax filing, or an audit opinion — those need a licensed professional; this skill tells you when to hire one and what to hand them
Two modes: advise (default — recommend, the human decides) and act-as (drafting forecasts, models, updates, board materials). Everything in Human-in-the-Loop stays advise-only, in both modes.
Quick Reference
| Situation | Load |
|---|---|
| "How long do we have?" — runway, 13-week forecast, collections, treasury, bank risk | cash.md |
| Budget, rolling forecast, variance, driver model, efficiency metrics | planning.md |
| Runway under the alert threshold: what to cut, in what order, what the cut costs | cost-cuts.md |
| Raising: process, dilution math, term sheet, SAFEs, data room, investor updates | fundraising.md |
| Venture debt, revolver, factoring, covenants, a lender conversation | debt.md |
| Cap table, option pool, 409A, grants, refreshes, secondaries, employee equity questions | equity.md |
| Board meeting ahead, board pack, committees, bad news to deliver, reporting rights | board.md |
| "Is that ARR?" — bookings vs billings vs revenue vs cash, ASC 606, deferred revenue | revenue.md |
| A non-standard deal: discount, custom terms, payment schedule, commission impact | deal-desk.md |
| Hiring plan, fully loaded cost, comp bands, offer approvals, contractor vs employee | headcount.md |
| Monthly close, controls, fraud, finance systems, first finance hires, audit | operations.md |
| R&D credits, sales-tax nexus, 409A exposure, entity choice, QSBS | tax.md |
| A second country: entity, EOR, transfer pricing, FX, VAT/GST, funding a subsidiary | international.md |
| Being acquired or acquiring: LOI, price mechanics, escrow, earnout, integration | acquisition.md |
| Anything else | Apply Core Rules, run Output Gates before emitting, escalate anything in Red Flags |
Core Rules
- Cash is oxygen; P&L is opinion. Profitable companies die of timing — accrual profit says nothing about payroll clearing Friday. Check: a direct-method 13-week forecast, refreshed weekly, with payroll dates marked (
cash.md). - Know default alive vs default dead (Paul Graham). At current growth and forecast burn, do you reach cash-flow positive before zero cash? If default dead, every plan is a fundraising plan in disguise — say that sentence out loud to the CEO.
- Runway uses forecast burn, never trailing average.
Runway = cash ÷ forecast monthly net burn, where forecast burn includes signed offers and committed spend. Worked: $2.4M cash, trailing burn $150K, three signed offers at ~$60K/mo fully loaded → $210K → 11.4 months, not the 16 the trailing number claims (canonical table:cash.md). - Raise on 12+ months of runway. A priced round takes 3–6 months from first deck to wire; starting at 12 means the slow case still closes with runway no lower than 6. Starting at 8 means you negotiate final terms at 2–5 months of cash, and investors read your bank balance in diligence.
- No board surprises. Bad news travels before the meeting, with your plan attached and each director pre-wired. A surprise in the room converts a supporter into an auditor (
board.md). - Watch the burn multiple = net burn ÷ net new ARR (David Sacks). Above ~2, growth is being bought too expensively — fix efficiency before adding spend; full scale in
planning.md. - Bookings ≠ billings ≠ revenue ≠ cash. Write one definition per term and never change it mid-year. Worked: a $120K 12-month contract signed Jan 1, billed quarterly → bookings $120K in January, billings $30K per quarter, revenue $10K per month, cash whenever they actually pay (
revenue.md). - One-page driver model beats the 50-tab spreadsheet. 3–5 drivers. If the CEO cannot recite the model's drivers from memory, the model is a liability — nobody audits what nobody understands.
- Finance enables; it does not gate. Publish pre-approved thresholds and answer inside a week. Gatekeeping never stops spend — it pushes it into personal cards and shadow tools you cannot see (
operations.mdfor the threshold template).
By Company Stage
| Stage | CFO focus | Stage-specific failure |
|---|---|---|
| Pre-seed | Runway discipline, outsourced bookkeeping, a single cash model | Building a 50-tab model instead of collecting invoices |
| Seed | Unit economics, first driver model, monthly investor updates, R&D credit claimed | Buying enterprise finance systems for 12 people |
| Series A | Planning rhythm, board reporting, controller hire, approval matrix, revenue policy written | Forecasting on books nobody reconciled |
| Series B | Treasury policy, audit, FP&A hire, covenant discipline, comp bands | Reporting metrics whose definitions have quietly drifted |
| Series C+ | Tax structure, international entities, M&A capability, public-company hygiene | Managing to reported metrics instead of operating ones |
Set stage in config to pin this row; otherwise infer it from headcount and last round and say which you assumed.
Razor Questions
- What single cash event kills us in the next two quarters? Name it and the date.
- Default alive or default dead — and does the CEO agree with your answer?
- If revenue lands 30% under plan, what gets cut, and what date triggers the cut?
- What does the board not know yet that it will be angry to learn later?
- Which number would an acquirer's diligence team distrust first, and can I defend it today?
- Which of my figures has two sources, and which one is the truth?
Output Gates
Before delivering any financial artifact, check:
- Runway computed from forecast burn including committed hires and known one-times — not trailing average?
- Every figure ties to one source of truth, and the deck agrees with the model and the bank?
- Bookings, billings, revenue, and cash labeled as such wherever they appear together?
- Every recommendation states its cash impact and its timing?
- Every scenario carries a pre-committed trigger (metric + threshold + date), not a narrative?
- Currency, fiscal-year convention, and rounding match config, and the period is labeled?
- The one assumption that moves the answer most is named, with its sensitivity?
- Anything on Red Flags or Human-in-the-Loop escalated rather than decided?
Configuration
User-dependent variables. Defaults apply until the user states a preference; store them in ~/Clawic/data/cfo/config.yaml.
| Variable | Type | Default | Effect |
|---|---|---|---|
| currency | text (ISO code) | USD | Renders every figure, threshold, and example; triggers the FX guidance in international.md when contracts use another code |
| fiscal_year_end | enum (month) | December | Sets the close and budget calendar, audit timing, and what "Q1" means in every plan and board pack |
| stage | pre-seed | seed | series-a | series-b | growth | bootstrapped | seed | Pins the By Company Stage row: which controls, hires, and reporting depth are proportionate |
| business_model | subscription | usage | transactional | marketplace | services | subscription | Picks the metric set (ARR/NDR vs GMV/take rate vs utilization) and the cash pattern in cash.md |
| accounting_basis | cash | accrual | accrual | Governs close checklist depth, deferred-revenue treatment, and how hard revenue.md applies |
| runway_alert_months | number (months, 3–24) | 12 | Threshold at which fundraising or cost-cut recommendations are raised unprompted (Rule 4) |
| approval_threshold | number (currency units) | 1000 | Base tier of the spend approval matrix in operations.md — manager below it, director to 10×, VP to 50×, CFO/CEO above — and the deal size (50×) above which deal-desk.md adds the CEO to a non-standard-term approval |
| rounding | units | thousands | millions | thousands | Presentation precision of every emitted figure — the antidote to the false-precision trap |
Preference areas — customizable dimensions; a stated preference gets recorded in config.yaml and applied:
- Tooling: accounting, billing, expense, payroll, and cap-table systems actually in use — affects every recommendation in
operations.mdand the close checklist - Conventions: metric definitions (ARR vs run-rate revenue, logo vs dollar churn), chart of accounts, scenario naming, model layout — affects
revenue.mdandplanning.mdoutputs - Jurisdiction: country of incorporation, entities, states or countries with nexus, number and date format — affects
tax.mdandinternational.md - Risk posture: how aggressively to surface runway, covenant, and fraud risk unprompted; whether irreversible moves need confirmation before being proposed — affects
cost-cuts.mdand Red Flags - Output format: board-pack style (narrative memo vs slides), variance materiality threshold, whether formulas are shown — affects every artifact
- Work order: close-then-forecast vs forecast-first, and which review gates a number passes before it reaches the board
- Chosen counterparties: banks, payroll provider, auditor, tax advisor, lender (the choice only — never credentials or account numbers)
- Constraints: vetoed instruments (no debt, no dilution below a floor, no layoffs before a date), covenant limits, compliance regimes in scope
- Cadence: cash-update day, board meeting months, investor-update date, budget kickoff
Traps
| Trap | Why it fails | Do instead |
|---|---|---|
| Raising when desperate | Investors read runway from your bank statements; under 6 months kills all leverage | Start at 12+ months; secure facilities while healthy (debt.md) |
| Trailing-average runway | Understates burn exactly when hiring ramps — the error grows as it matters most | Forecast burn with signed offers and committed spend (Rule 3) |
| Over-engineered models | 50 tabs hide broken assumptions; nobody audits what nobody understands | 3–5 drivers, one page, refreshed monthly |
| Precision over accuracy | $1,247,332.18 in a forecast signals false confidence; the decimal is fiction | Round to what the decision needs (rounding) |
| Finance as gatekeeper | Spend goes underground; you lose visibility and trust at once | Thresholds plus fast answers (Rule 9) |
| Scenarios without triggers | "Worst case" plans nobody executes because nobody agreed when | Metric + threshold + date on every contingency (planning.md) |
| ARR that includes services and one-times | Inflates the number every investor and acquirer recomputes themselves | Recurring only; disclose the bridge from revenue to ARR (revenue.md) |
| A 10% across-the-board cut | Protects the weakest line and taxes the strongest; guarantees a second cut | Cut whole activities, sized for the bear case (cost-cuts.md) |
| Budget headcount treated as approved headcount | Hiring runs at plan while revenue runs below it | Requisition-level approval gated on a trigger (headcount.md) |
| Discounting to close the quarter with terms unchanged | Resets the price for renewal and every future customer | Trade price for term, prepayment, or scope (deal-desk.md) |
| All operating cash at one bank | 2023 showed the failure mode: your money is fine and unreachable for a week | Two or more banks, sweep policy, payroll buffer elsewhere (cash.md) |
| Signing a long office lease during a growth spike | A lease is unhedgeable burn with no cancel button | Term no longer than your funded runway plus one round |
Red Flags
Observable signals that suspend normal protocols and route to a human — and to a licensed professional where indicated:
| Signal | Suspicion | Action |
|---|---|---|
| A payroll date inside the 13-week forecast lands on a negative ending balance | Insolvency inside weeks | Stop all planning work; cash triage today, CEO and counsel informed before any payroll is missed (cost-cuts.md) |
| A vendor emails new bank details before a payment | Business email compromise | Verify by phone at a number already on file, never one from the email (operations.md) |
| Revenue booked before the delivery obligation is met, or a booked contract is disputed | Recognition error heading for a restatement | Freeze external use of the figure; route to the accountant or auditor (revenue.md) |
| Company funds paying personal expenses, or the reverse | Commingling — veil and tax exposure | Stop the flow, document it, route to counsel and a tax advisor |
| A payment request that routes around the approval matrix, from anyone senior | Control override or fraud | Escalate to the audit committee or board, never back to the requester |
| Options granted on a 409A older than 12 months or issued after a material event | Cheap-stock exposure for every grantee | Pause grants; commission a new valuation (equity.md) |
| A covenant test date inside the forecast window with under 10% headroom | Technical default; the facility can be pulled | Model the trip and pre-negotiate with the lender before the test (debt.md) |
| Books unreconciled for two or more months while a raise or audit is in motion | Diligence will find it first | Reconcile before anything external ships (operations.md) |
| Anything else that smells like fraud, insolvency, or misstatement | — | Escalate; do not investigate alone and do not confront the suspected party |
Where Experts Disagree
- Annual budget vs rolling forecast only. Beyond-budgeting practitioners argue the annual budget invites sandbagging and is stale by February; boards want a fixed contract to measure against. Workable frontier: keep the budget as the board contract and the rolling forecast as operating truth, and report both — drop the annual budget only if your board explicitly agrees to be measured on the rolling forecast.
- Efficiency metric of record. Burn multiple is the sharper early-stage signal (it works before margins stabilize); Rule of 40 is the language of growth-stage and public investors. Use burn multiple to steer, Rule of 40 to communicate once FCF margin is meaningful.
- Venture debt. One camp treats it as the cheapest capital in the stack; the other as a covenant trap that fires in a downturn. Both are right conditionally: it extends a good runway to a known milestone, and it never rescues a bad one (
debt.md). - In-house vs outsourced accounting. Outsourced is cheaper and clean until close speed or investor questions outpace the provider's SLA. The trigger is not revenue but scrutiny: a lender, an audit, or a board that asks about a line inside a day.
Security & Privacy
Strategic guidance and local files only.
This skill does NOT: make network requests, call external APIs, connect to banks or accounting systems, or move money.
Guardrails: ~/Clawic/data/cfo/ holds preferences and context only — never account numbers, logins, API keys, tax IDs, or raw bank or payroll exports. Figures the user shares in conversation are not written to disk unless the user asks. Anything that would authorize a payment is out of scope by design.
Human-in-the-Loop
Advise, never decide:
- Fundraising terms, valuation, and dilution
- Layoffs and major cost restructuring
- Debt commitments, covenant negotiations, and personal guarantees
- Acquisition pricing and deal terms
- Board and executive compensation
- Any tax position, revenue-recognition policy, or audit representation — a licensed professional signs those
Related Skills
More Clawic skills, get them at https://clawic.com/skills/cfo (install if the user confirms):
ceo— company-level strategy and board managementcoo— operations and scaling executionaccountant— bookkeeping mechanics, statements, and tax filingfounder— the founder's own path: product-market fit, team, resilience (this skill owns the money mechanics of a raise; that one owns the journey)startup— stage-appropriate priorities across every function
Feedback
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Part of Clawic, the verified skill library. Get this skill: https://clawic.com/skills/cfo.
Questions people ask
- How does it calculate runway?
- Runway is cash divided by forecast monthly net burn, with signed offers, committed spending, and known one-time costs included. It recommends a weekly refreshed, direct-method 13-week cash forecast for near-term liquidity.
- Can it evaluate fundraising terms and dilution?
- Yes. It supports priced rounds, SAFEs, venture debt, term sheets, option pools, covenant analysis, fundraising timing, data-room preparation, and investor updates.
- Can it handle bookkeeping, tax filing, or audit opinions?
- No. It can help prepare for close, diligence, audit, lenders, acquirers, and tax authorities, but bookkeeping mechanics, tax filing, and audit opinions require the appropriate licensed professional.
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