C Level Advisor

Chief AI Officer advisory for startups: model build-vs-buy decisions (API vs fine-tune vs in-house), AI risk classification under EU AI Act + US state patchwork, AI cost economics (API-to-self-hosted breakeven), and AI team org evolution. Use when deciding whether to call an API or fine-tune, classifying AI use cases for regulatory risk, calculating when self-hosting pays off, sequencing AI hires, or when user mentions CAIO, AI strategy, model selection, foundation model, fine-tuning, EU AI Act, NIST AI RMF, AI governance, model risk, or AI economics. Strategic only — does not duplicate engineering AI/ML skills.

Chief Customer Officer advisory for startups: retention decomposition (gross retention vs NRR honesty, churn root-cause taxonomy), customer segmentation strategy (differential investment across tiers + ICP fit scoring), CS team coverage model (pooled vs named CSM thresholds + ratio math), and CS team org evolution (CS vs Support vs AM distinctions). Use when designing retention strategy, segmenting customers for differential investment, sizing CS team, or sequencing CS hires. Strategic only — does not duplicate engineering/business-growth tactical skills.

Chief Data Officer advisory for startups: AI training data rights and consent provenance, data product strategy (warehouse vs lakehouse vs mesh, build-vs-buy), B2B customer-data-as-asset valuation and M&A readiness, data team org evolution. Use when deciding whether to train models on customer data, choosing data architecture, valuing data for fundraising or M&A, sequencing data hires, or when user mentions CDO, chief data officer, data strategy, data mesh, lakehouse, training data, data product, data monetization, or customer data asset. NOT a tactical data engineering skill — strategic decisions only.

General Counsel advisory for startups: contract review (MSA, SaaS, NDA, DPA, employment), IP strategy, term sheet decoding, and regulatory landscape mapping. Use when reviewing any contract or term sheet, deciding when to engage outside counsel, defining IP strategy, evaluating regulatory exposure (HIPAA, GDPR, FDA, fintech), or when user mentions general counsel, GC, legal review, contract risk, term sheet, IP assignment, or regulatory exposure. NOT a substitute for licensed counsel — surfaces questions to bring to qualified attorneys.

Inter-agent communication protocol for C-suite agent teams. Defines invocation syntax, loop prevention, isolation rules, and response formats. Use when C-suite agents need to query each other, coordinate cross-functional analysis, or run board meetings with multiple agent roles.

Assembles comprehensive board and investor update decks by pulling perspectives from all C-suite roles. Use when preparing board meetings, investor updates, quarterly business reviews, or fundraising narratives. Covers structure, narrative framework, bad news delivery, and common mistakes.

Multi-agent board meeting protocol for strategic decisions. Runs a structured 6-phase deliberation: context loading, independent C-suite contributions (isolated, no cross-pollination), critic analysis, synthesis, founder review, and decision extraction. Use when the user invokes /cs:board, calls a board meeting, or wants structured multi-perspective executive deliberation on a strategic question.

10 C-level advisory agent skills and plugins for Claude Code, Codex, Gemini CLI, Cursor, OpenClaw. CEO, CTO, COO, CPO, CMO, CFO, CRO, CISO, CHRO, Executive Mentor. Multi-role board meetings, strategy routing, structured recommendations. For founders needing executive-level decision support.

Executive leadership guidance for strategic decision-making, organizational development, and stakeholder management. Use when planning strategy, preparing board presentations, managing investors, developing organizational culture, making executive decisions, fundraising, or when user mentions CEO, strategic planning, board meetings, investor updates, organizational leadership, or executive strategy.

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.

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, accountability chart, or quarterly planning.

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.

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 development, delegation, burnout, or imposter syndrome.

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.

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.

VP of Engineering advisory for startups: delivery throughput (DORA 4 metrics + bottleneck identification), engineering hiring funnel (sourcing → screen → onsite → offer conversion + time-to-fill + pipeline gap), engineering team structure (squad/tribe/chapter design + tech-lead manager-trigger thresholds), and production discipline (on-call, deployment cadence, postmortem culture). Use when sprint velocity is dropping, eng hiring is broken, team structure is unclear, or deciding when to add a tech-lead manager. NOT a CTO skill (which owns architecture) — VPE owns delivery operations and how the team ships.