Explore skills

/cs:vpe-review <plan> — Throughput-first VP of Engineering interrogation of any plan that touches delivery, eng hiring, team structure, or production discipline.

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,

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, segmentin

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 use

Board meeting preparation for the adversarial scenario, not the friendly one. Forces numbers-cold mastery, anticipates hard questions, builds a narrative that acknowledges weakness without losing the room. Use when preparing for a board meeting, an investor update, fundraising presentation, or any high-stakes adversarial review where every number must live in your head not just on a slide.

Pre-mortem plan analysis. Imagine the plan failed 12 months from now and work backwards to find the weaknesses. Surfaces assumptions, dependencies, and execution risks before committing resources. Use when before significant resource commitment, before presenting to a board or investors, when feedback has been one-sidedly positive, or when there is pressure to move fast and figure it out later.

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.

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

/em -stress-test — Business Assumption Stress Testing

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,

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.