c-level-advisor

Financial leadership for startups and scaling companies. Financial modeling, unit economics, fundraising strategy, cash management, and board financial packages. Use when building financial models, analyzing unit economics, planning fundraising, managing cash runway, preparing board materials, or when user mentions CFO, burn rate, runway, fundraising, unit economics, LTV, CAC, term sheets, or financial strategy.

/em -challenge — Pre-Mortem Plan Analysis

Framework for rolling out organizational changes without chaos. Covers the ADKAR model adapted for startups, communication templates, resistance patterns, and change fatigue management. Handles process changes, org restructures, strategy pivots, and culture changes. Use when announcing a reorg, switching tools, pivoting strategy, killing a product, changing leadership, or when user mentions change management, change rollout, managing resistance, org change, reorg, or pivot communication.

C-suite orchestration layer. Routes founder questions to the right advisor role(s), triggers multi-role board meetings for complex decisions, synthesizes outputs, and tracks decisions. Every C-suite interaction starts here. Loads company context automatically.

People leadership for scaling companies. Hiring strategy, compensation design, org structure, culture, and retention. Use when building hiring plans, designing comp frameworks, restructuring teams, managing performance, building culture, or when user mentions CHRO, HR, people strategy, talent, headcount, compensation, org design, retention, or performance management.

Security leadership for growth-stage companies. Risk quantification in dollars, compliance roadmap (SOC 2/ISO 27001/HIPAA/GDPR), security architecture strategy, incident response leadership, and board-level security reporting. Use when building security programs, justifying security budget, selecting compliance frameworks, managing incidents, assessing vendor risk, or when user mentions CISO, security strategy, compliance roadmap, zero trust, or board security reporting.

Marketing leadership for scaling companies. Brand positioning, growth model design, marketing budget allocation, and marketing org design. Use when designing brand strategy, selecting growth models (PLG vs sales-led vs community-led), allocating marketing budgets, building marketing teams, or when user mentions CMO, brand strategy, growth model, CAC, LTV, channel mix, or marketing ROI.

The meta-framework for how a company runs — the connective tissue between all C-suite roles. Covers operating system selection (EOS, Scaling Up, OKR-native, hybrid), accountability charts, scorecards, meeting pulse, issue resolution, and 90-day rocks. Use when setting up company operations, selecting a management framework, designing meeting rhythms, building accountability systems, implementing OKRs, or when user mentions EOS, Scaling Up, operating system, L10 meetings, rocks, scorecard, accoun

Systematic competitor tracking that feeds CMO positioning, CRO battlecards, and CPO roadmap decisions. Use when analyzing competitors, building sales battlecards, tracking market moves, positioning against alternatives, or when user mentions competitive intelligence, competitive analysis, competitor research, battlecards, win/loss, or market positioning.

Loads and manages company context for all C-suite advisor skills. Reads ~/.claude/company-context.md, detects stale context (>90 days), enriches context during conversations, and enforces privacy/anonymization rules before external API calls.

Operations leadership for scaling companies. Process design, OKR execution, operational cadence, and scaling playbooks. Use when designing operations, setting up OKRs, building processes, scaling teams, analyzing bottlenecks, planning operational cadence, or when user mentions COO, operations, process improvement, OKRs, scaling, operational efficiency, or execution.

Product leadership for scaling companies. Product vision, portfolio strategy, product-market fit, and product org design. Use when setting product vision, managing a product portfolio, measuring PMF, designing product teams, prioritizing at the portfolio level, reporting to the board on product, or when user mentions CPO, product strategy, product-market fit, product organization, portfolio prioritization, or roadmap strategy.

Revenue leadership for B2B SaaS companies. Revenue forecasting, sales model design, pricing strategy, net revenue retention, and sales team scaling. Use when designing the revenue engine, setting quotas, modeling NRR, evaluating pricing, building board forecasts, or when user mentions CRO, chief revenue officer, revenue strategy, sales model, ARR growth, NRR, expansion revenue, churn, pricing strategy, or sales capacity.

Founder onboarding interview that captures company context across 7 dimensions. Invoke with /cs:setup for initial interview or /cs:update for quarterly refresh. Generates ~/.claude/company-context.md used by all C-suite advisor skills.

Technical leadership guidance for engineering teams, architecture decisions, and technology strategy. Use when assessing technical debt, scaling engineering teams, evaluating technologies, making architecture decisions, establishing engineering metrics, or when user mentions CTO, tech debt, technical debt, team scaling, architecture decisions, technology evaluation, engineering metrics, DORA metrics, or technology strategy.

Build, measure, and evolve company culture as operational behavior — not wall posters. Covers mission/vision/values workshops, values-to-behaviors translation, culture code creation, culture health assessment, and cultural rituals by stage. Use when building company values, assessing culture health, designing cultural rituals, creating culture codes, handling culture clashes, or when user mentions culture, values, culture debt, founder culture, or culture code.

Two-layer memory architecture for board meeting decisions. Manages raw transcripts (Layer 1) and approved decisions (Layer 2). Use when logging decisions after a board meeting, reviewing past decisions with /cs:decisions, or checking overdue action items with /cs:review. Invoked automatically by the board-meeting skill after Phase 5 founder approval.

Adversarial thinking partner for founders and executives. Stress-tests plans, prepares for brutal board meetings, dissects decisions with no good options, and forces honest post-mortems. Use when you need someone to find the holes before the board does, make a decision you've been avoiding, or understand what actually went wrong.

Personal leadership development for founders and first-time CEOs. Covers founder archetype identification, delegation frameworks, energy management, CEO calendar audits, leadership style evolution, blind spot identification, imposter syndrome, founder mental health, and succession planning. Use when a founder feels like the bottleneck, struggles to delegate, is burning out, transitioning from IC to executive, managing a board, or when user mentions founder mode, CEO growth, leadership developmen

/em -hard-call — Framework for Decisions With No Good Options

Build and maintain one coherent company story across all audiences — employees, investors, customers, candidates, and partners. Detects narrative contradictions and ensures the same truth is framed for each audience's needs. Use when preparing investor updates, all-hands presentations, board communications, recruiting narratives, crisis communications, or when user mentions company narrative, messaging consistency, storytelling, all-hands, investor update, or crisis communication.

International market expansion strategy. Market selection, entry modes, localization, regulatory compliance, and go-to-market by region. Use when expanding to new countries, evaluating international markets, planning localization, or building regional teams.

M&A strategy for acquiring companies or being acquired. Due diligence, valuation, integration, and deal structure. Use when evaluating acquisitions, preparing for acquisition, M&A due diligence, integration planning, or deal negotiation.

Cross-functional organizational health check combining signals from all C-suite roles. Scores 8 dimensions on a traffic-light scale with drill-down recommendations. Use when assessing overall company health, preparing for board reviews, identifying at-risk functions, or when user mentions org health, health check, or health dashboard.

/em -postmortem — Honest Analysis of What Went Wrong

Cross-functional what-if modeling for cascading multi-variable scenarios. Unlike single-assumption stress testing, this models compound adversity across all business functions simultaneously. Use when facing complex risk scenarios, strategic decisions with major downside, or when the user asks 'what if X AND Y both happen?

Cascades strategy from boardroom to individual contributor. Detects and fixes misalignment between company goals and team execution. Covers strategy articulation, cascade mapping, orphan goal detection, silo identification, communication gap analysis, and realignment protocols. Use when teams are pulling in different directions, OKRs don't connect, departments optimize locally at company expense, or when user mentions alignment, strategy cascade, silo, conflicting OKRs, or strategy communication

/em -stress-test — Business Assumption Stress Testing