Forecast cash, calculate runway, model financing, and prepare finance decisions for boards and founders.
214 installs7 stars
Coding
CEO / Chief Executive Officer
Pressure-test CEO decisions and draft plans, memos, and communications with explicit approval gates.
What it does
Pressure-test company-level decisions on strategy, cash, executive teams, boards, crises, acquisitions, and shutdowns. Advice is adapted to company stage, funding model, runway, jurisdiction, and whether the call is reversible. It can counsel a CEO or draft the decision, plan, memo, and message, while requiring human sign-off for consequential external actions.
When to use it
- Pressure-testing a pivot or shutdown
- Planning a raise-or-cut decision
- Preparing a contentious board meeting
- Handling an executive exit or company crisis
The skill document
User preferences, company context, and memory live in ~/Clawic/data/ceo/ (see setup.md on first use, memory-template.md for the file format). If you have data at an old location (~/ceo/ or ~/clawic/ceo/), move it to ~/Clawic/data/ceo/.
When To Use
- Making or pressure-testing a company-level call: pivot, raise, cut, reorg, exec hire or exit, acquisition, shutdown.
- Preparing board meetings, investor updates, all-hands, or bad-news communications.
- Sizing runway, burn, or fundraise timing before committing spend or headcount.
- Navigating a crisis: cash, breach, PR, key departure, product failure, market shift, co-founder conflict.
- Stepping into the seat (new CEO, promoted founder) or planning to hand it over.
- Not for functional depth: financial models, forecasts, and dilution or term-sheet math →
cfo(the CEO keeps the decision, cfo owns the mechanics), go-to-market →cmo, operational execution →coo, architecture →cto.
Two modes, set by mode in Configuration: advise (default — counsel a human CEO or founder; recommend, they decide) and act-as (draft the decision, plan, or communication directly). In both modes, everything under Human-in-the-Loop requires explicit human sign-off before it leaves the building.
Quick Reference
| Situation | Load |
|---|---|
| Choosing direction, killing projects, moat analysis, annual plan | strategy.md |
| A big call is stuck, the team is split, or decision quality matters | decisions.md |
| Which numbers to run the company on, dashboard and review cadence | metrics.md |
| Board meeting ahead, bad news to deliver, investor gone quiet | board.md |
| Runway inside the alarm threshold, term sheet in hand, bridge question | fundraising.md |
| Burn, scenarios, unit economics, valuation sanity check | finance.md |
| Price change, discount creep, packaging or willingness-to-pay question | pricing.md |
| Exec hiring/firing, comp, performance, culture drift | people.md |
| Headcount jumped and things that worked stopped working | scaling.md |
| Cutting the team: sizing, selection, notice, severance, survivors | layoffs.md |
| Writing the all-hands, the memo, the press line, the hard message | communication.md |
| Something is on fire right now — cash, breach, outage, misconduct, press | crisis.md |
| The current direction is not working; persevere-or-pivot | pivot.md |
| A rival raised, copied the product, cut price, or poached staff | competition.md |
| Top-account escalation, churn save, concentration risk, firing a customer | customers.md |
| Channel, OEM, reseller, or "strategic" partnership on the table | partnerships.md |
| Buying a company, an acquihire, or integrating one | acquisitions.md |
| Someone offered to buy you, or you want to run a sale process | exit.md |
| Co-founder equity, role overlap, conflict, or departure | cofounders.md |
| Cap table, 409A, minutes, IP assignment, fiduciary duty, compliance | governance.md |
| First weeks in the seat: listening tour, early wins, team read | first-90-days.md |
| Replacing the CEO, founder-to-professional transition, handoff | succession.md |
| Out of options: wind-down mechanics, priority of payments, notice | shutdown.md |
| Sponsor board, covenants, EBITDA plan, hold-period clock | pe-backed.md |
| First country outside the home market: entity, EOR, country lead | international.md |
| Own calendar, exec meetings, decision queue, self-management | ceo-operating-system.md |
| Anything else | Core Rules and Output Gates below; if it is not company-level, route to the functional skill in Related Skills |
Core Rules
- Only three jobs are undelegable (Fred Wilson): set and communicate vision/strategy, recruit and retain the top team, make sure there is always enough cash. Everything else gets a named owner. Check: does this week's calendar map to those three?
- Three priorities maximum — a fourth makes the first three negotiable. Check: name what you explicitly killed this quarter; if nothing died, you have a list, not a strategy.
- Match speed to reversibility. Two-way door → decide at ~70% of the information you wish you had (Bezos, 2016 shareholder letter), delegate, correct later. One-way door (pivot, exec exit, term sheet, layoff, sale) → pre-mortem first. Tiebreak when the type is unclear: if a week of delay costs more than a wrong-but-correctable call, decide now (→
decisions.md). - Know if you are default alive (Paul Graham): at current growth rate and burn, does revenue cross expenses before cash hits zero? If not, every plan is a fundraising plan whether it says so or not. Arithmetic of the alarm: a round runs 3-6 months end to end, close included, so 9 months of runway is the hard floor to start one;
runway_alarm_months(default 12) starts it a quarter earlier, which is where the leverage is. Canonical runway zone table:finance.md; nothing else re-labels the bands (→fundraising.md). - Cut once, sized on the bear case. Target runway after the cut = months to the next fundable milestone + 6, computed with revenue flat and no new round. Example: milestone is 9 months out → cut deep enough to hold 15 months at bear-case revenue. A second layoff destroys more trust than one deep cut (Horowitz) — undersizing the first is the expensive error (→
layoffs.md). - No board surprises — pre-wire every contentious topic with each director 3-7 days out, 15-30 minutes each; the meeting confirms decisions, it does not make them (→
board.md). - Culture = what you tolerate: the behavior of the best performer you refuse to correct becomes policy. Check: whose behavior are you currently excusing because of their numbers?
- Declare peacetime or wartime (Horowitz) and say which one out loud. Wartime centralizes decisions, tolerates less deviation from plan, and communicates bluntly; blending the two modes reads to the team as inconsistency, not flexibility.
- Every consequential call leaves a record: one named owner, the decision date, a review date, and the falsifier — the observation that would change your mind. Missing the falsifier is how a decision becomes an identity (→
decisions.md).
By Company Stage
| Stage | CEO focus | Stage-specific failure |
|---|---|---|
| Pre-PMF | Weekly customer contact, fast iteration, retention signal, guard runway | Scaling spend before retention proves PMF |
| Seed | Find the repeatable motion, hire the first 10 well, stay default alive | Hiring a sales team before the founder can sell it |
| Series A | Repeatable go-to-market, first exec hires, board rhythm | Hiring execs built for a company two stages larger |
| Series B | Delegate operations, org design, second bet | CEO still deciding everything — becomes the rate limiter |
| Growth / C+ | Multi-product, M&A, succession, public-company hygiene | Managing to reported metrics instead of operating metrics |
| Public | Guidance discipline, capital allocation, investor narrative | Optimizing the quarter at the cost of the next three years |
By Operating Context
funding_model decides which scoreboard the CEO is actually being graded against. Getting this wrong produces confident advice aimed at the wrong finish line.
| Context | The real scoreboard | Where it changes the job |
|---|---|---|
| VC-backed | Growth rate against the next round's bar | Fundraising clock governs; fundraising.md, finance.md |
| Bootstrapped | Owner cash flow and optionality | No raise deadline; pricing and retention carry the load — pricing.md, customers.md |
| PE-backed | EBITDA and leverage against the value-creation plan | Sponsor board, covenants, exit clock — pe-backed.md |
| Family / SMB | Continuity, family alignment, distributions | Governance and succession dominate — succession.md, governance.md |
| Nonprofit | Mission outcomes per funded dollar, funder concentration | Board is boss and fundraiser; board.md with donors substituted for investors |
| Unclear | Ask one question: who can fire you, and what number do they watch? | Answer routes to the row above |
Human-in-the-Loop
Draft freely; a human signs before any of these leaves the room:
- Major pivots, shutdowns, or a decision to sell
- Executive terminations, layoffs, or any individual's compensation
- Fundraising term negotiations and signed term sheets
- M&A decisions on either side
- Crisis public communications, regulatory filings, and press statements
- Board seat changes and anything requiring a board vote or written consent
In act-as mode this is the whole boundary: the skill writes the memo, the plan, the model, and the message — a human sends it.
Output Gates
Before issuing a recommendation, decision, or communication, check:
- Did I establish stage, runway in months, funding model, and board composition? Advice that skips these defaults to generic Series-B peacetime advice.
- Is this a one-way or two-way door, and does my recommended speed match (rule 3)?
- Does it carry one named owner, a review date, and a falsifier (rule 9)?
- If it is bad news, does the plan travel with it? Never hand a board or team a problem without the proposed response.
- Can the current team execute this, or does it assume execs the company does not have?
- Is every number in it computed from this company's inputs rather than a benchmark I recalled — and stated in
currency? - Does every legal step in it (notice periods, consultation, filings, equity or tax elections) match
jurisdictionrather than the US-Delaware default the guides assume?
Configuration
User-dependent variables. Defaults apply until the user states a preference; store them in ~/Clawic/data/ceo/config.yaml.
| Variable | Type | Default | Effect |
|---|---|---|---|
| mode | advise | act-as | advise | advise recommends and hands the call to the human; act-as drafts decisions, memos, and plans directly. Human-in-the-Loop applies in both |
| stage | pre-pmf | seed | series-a | series-b | growth | public | seed | Selects the By Company Stage row, plus default dilution, equity, and board-composition ranges in fundraising.md, people.md, board.md |
| funding_model | vc | bootstrapped | pe-backed | family | nonprofit | vc | Selects the By Operating Context row: which success metric governs and which file is authoritative |
| business_model | b2b-saas | plg | marketplace | consumer-sub | ecommerce | services | hardware | pre-pmf | b2b-saas | Selects the Pick The Model First row in metrics.md: the primary health metric, its predictor, and the vanity substitute to refuse |
| runway_alarm_months | number (3-24) | 12 | Month count at which cash becomes priority one and rule 4 triggers raise-or-cut planning; enters the zone table in finance.md |
| currency | ISO code | USD | Units for every burn, comp, valuation, and severance figure produced |
| jurisdiction | region code (US-DE, US-CA, US-NY, UK, EU-DE, …) | US-DE | Selects which legal branch applies: notice, mini-WARN and consultation rules in layoffs.md, equity and tax mechanics (83(b), 409A, QSBS) in governance.md and cofounders.md, wind-down procedure in shutdown.md, hiring vehicle in international.md |
| concentration_threshold | number (% of revenue, 5-30) | 10 | Revenue share above which one account becomes a board topic and a risk-page entry in customers.md; 2× it is the hard-risk line |
| discount_authority | list (role:max %) | rep:10, vp:20, ceo:above | Caps in the authority ladder in pricing.md; approvals above the top rung get logged and reviewed monthly |
| fiscal_year_start | month | January | Anchors the planning calendar in strategy.md and the board rhythm in board.md |
| planning_framework | OKR | V2MOM | EOS | none | OKR | Shapes goal setting, the quarterly review, and the annual plan template |
| board_cadence | monthly | quarterly | quarterly | Sets pre-wire timing, deck depth, and update rhythm in board.md and communication.md |
| deliverable_style | memo | bullets | deck-outline | memo | Format of drafted board updates, all-hands scripts, and decision write-ups |
| voice_file | path | none | Long-form voice sample at ~/Clawic/data/ceo/; overrides the default register in every drafted communication |
Preference areas — customizable dimensions; a stated preference gets recorded in config.yaml and applied:
- Risk posture — buffer insisted on before spend, depth of a cut, tolerance for one-way doors; affects rules 3-5,
layoffs.mdsizing,finance.mdscenarios - Transparency — what the whole company sees (runway, metrics, board material) versus execs only; affects
communication.mdand all-hands content - Delegation surface — which decisions the CEO keeps versus assigns; affects Who Decides What in
decisions.mdand the calendar inceo-operating-system.md - Red lines — practices, markets, investors, or acquirers ruled out in advance; checked before any recommendation in
fundraising.md,exit.md,partnerships.md - Legal and regulatory regime — incorporation form, employment-law regime, data and privacy rules, sector licensing beyond what
jurisdictionalone selects; affectslayoffs.md,governance.md,international.md,shutdown.md - Cadence — board, all-hands, 1:1, offsite, and investor-update frequency; overrides the default rhythms in
ceo-operating-system.md - Company context — stage facts the user declares (board roster, cap table shape, key accounts) recorded in
~/Clawic/data/ceo/company.mdand read before advising
Traps
| Trap | Why it fails | Do instead |
|---|---|---|
| Skipping board pre-wiring | Directors decide cold, in the room, anchored by the loudest voice | 15-30 min call with each director before every consequential meeting (rule 6) |
| Hiring a senior exec mid-crisis | A wrong exec costs 6-12 months, landing exactly when you cannot afford it | Interim internal owner or fractional exec until stable (people.md) |
| Ignoring runway until under 6 months | Desperation raise: bad terms, wrong partners, zero leverage | Review runway weekly; start the process at runway_alarm_months (rule 4) |
| Five or more priorities | Teams optimize locally; nothing compounds | Three max, published with the kill list |
| Avoiding the hard conversation | The problem compounds and the team learns you tolerate it | Same-week feedback; decisions.md if genuinely stuck |
| Delegating culture to HR | Culture is set by promotion and firing decisions — only the CEO makes those at the top | Use the levers in people.md yourself |
| Founder mode on everything, forever | You become the org's bottleneck | Delegate by task-relevant maturity (Grove): per task, not per person |
| Reading quick consensus as alignment | On a big bet, fast agreement means the debate never happened | Assign a dissenting voice before deciding (→ decisions.md) |
| Announcing a decision the team learns of secondhand | Rumor beats the memo; the message becomes about the leak | Sequence the comms before you decide the date (communication.md) |
| Treating one loud customer as the market | Roadmap bends to whoever escalates hardest | Weight by cohort and revenue concentration (customers.md) |
Where Experts Disagree
- Growth versus default alive. Blitzscaling (Hoffman) accepts inefficiency to win a winner-take-most market; default alive (Graham) treats dependence on the next round as the risk itself. The condition, not the doctrine: winner-take-most dynamics plus available capital favor speed; anything else favors control of your own timeline.
- Founder mode versus professional management. Graham's founder mode says the CEO should keep hands on specific surfaces; the classic answer is hire great people and let them run. Boundary: keep the surfaces where your judgment is the product (strategy, top hires, the thing customers love); delegate where a professional beats you on a bad day.
- Radical transparency versus need-to-know. Sharing runway, board decks, and full metrics builds trust and speeds decisions; it also converts a bad quarter into attrition risk. Condition: transparency scales down as the number of people who can act on the information does.
- Founder control versus a strong board. Keeping control preserves conviction through the hard middle; a real board catches the failure modes founders cannot see in themselves. The tiebreak is not the cap table — it is whether you have anyone who can tell you no and be heard (
board.md).
Related Skills
More Clawic skills, get them at https://clawic.com/skills/ceo (install if the user confirms):
cfo— financial modeling, forecast, close, and dilution mathcoo— operations and scaling executioncmo— marketing strategy and growthcto— technical leadership and architecturebusiness— strategy validation and planning
Feedback
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- Latest version: https://clawic.com/skills/ceo
Part of Clawic, the verified skill library. Get this skill: https://clawic.com/skills/ceo.
Questions people ask
- What context does it need before recommending a decision?
- It establishes the company stage, runway in months, funding model, and board composition. Configuration can also cover business model, currency, jurisdiction, planning framework, and other operating constraints.
- Can it draft board, investor, layoff, or crisis communications?
- Yes. It can prepare board materials, investor updates, all-hands messages, bad-news communications, and crisis statements, but a human must approve sensitive communications and actions before they leave the organization.
- Does it replace specialist finance, marketing, operations, or technical work?
- No. It keeps the company-level decision with the CEO while routing financial models and term-sheet math to CFO work, go-to-market to CMO work, execution to COO work, and architecture to CTO work.
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