executive-mentor

General Counsel advisory for startups: contract risk scanner (12 founder-killer patterns: auto-renew traps, uncapped indemnity, vague IP, MFN pricing, missing DPA, one-sided venue, broad non-solicit, perpetual license-back, etc.) and term sheet analyzer (0-100 founder-friendliness score across 12 dimensions: liquidation preference, anti-dilution, option pool, board, vesting, drag-along, protective provisions, info rights, dividends, valuation). 3 in-depth references: contracts playbook (7 startup contract types), IP + regulatory landscape (HIPAA, GDPR, FDA, fintech, EU AI Act + SOC 2 to ISO sequencing), term sheet decoder. Stdlib-only. Standalone-installable; also bundled in c-level-skills. NOT a substitute for licensed counsel.

Chief Data Officer advisory: AI training data audit (origin x class x use-case matrix with GDPR Art. 6 + EU AI Act citations -> GO/MITIGATE/NO-GO per source), data product strategy picker (warehouse vs lakehouse vs mesh + 6-layer build-vs-buy + 12-month sequencing), data asset valuator (strategic value 0-10 + M&A multiplier with carve-out penalties + 3 ranked productization paths). 4 references answering one decision each: training rights, data product strategy, customer-data-as-asset, data team org evolution. Stdlib-only. Standalone-installable; also bundled in c-level-skills. Strategic only - does not duplicate engineering data skills.

Company Architect: builds a business from scratch as an OKF (Open Knowledge Format) bundle — a tree of version-controllable .md files with frontmatter type, links forming a graph, and reserved index.md/log.md, readable by humans and agents. Guides the founder through a 12-phase interview (foundation, strategy, market, financial, sales, marketing, product, operations, tech, people, legal, governance), one phase at a time, and generates conformant markdown concepts. 3 stdlib tools: scaffold_bundle (bundle scaffolding), okf_linter (validates type/reserved files/links), index_generator (regenerates the index.md files). Standalone-installable; also bundled in c-level-skills.

VP of Engineering advisory: delivery throughput analyzer (DORA 4 metrics + cycle-time bottleneck identification), eng hiring funnel calculator (7-stage conversion + pipeline gap + weakest-stage fixes), eng team structure designer (squad/tribe model + manager-trigger + director-trigger + span-of-control). 4 in-depth references: DORA framework, eng hiring funnel, eng team structure (Conway's Law), production discipline (on-call, incidents, deployment, SLOs). Stdlib-only. Standalone-installable; also bundled in c-level-skills. NOT a CTO skill — VPE owns how the team ships, CTO owns what to build.

Chief AI Officer advisory: model build-vs-buy calculator (API vs fine-tune vs build with 3-year TCO across 6 paths + breakeven balancing economics with practical feasibility), AI risk classifier (EU AI Act tier with 7 Article citations + US state patchwork: NYC LL 144, CO AI Act, IL HB 53, CA SB 1001, IL BIPA + industry overlays for FDA AI/ML, CFPB Circular 2023-03, NYDFS Reg 23, NAIC, ECOA, Fed SR 11-7), AI cost economics (API vs self-hosted breakeven with 2026 pricing across A100/H100, utilization reality, hidden costs). 4 in-depth references each citing 5+ authoritative sources. Stdlib-only. Standalone-installable; also bundled in c-level-skills. Strategic only - does not duplicate engineering AI/ML skills.