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Found 23 Skills
Use when making architecture decisions, evaluating build-vs-buy, planning tech stack, prioritizing tech debt, writing PRDs, or needing strategic technical leadership
Apply startup execution wisdom to product, strategy, and business decisions. Use for feature prioritization, build-vs-buy decisions, go-to-market planning, pricing, hiring, scope/timeline reality checks, or when evaluating whether an idea has product-market fit potential.
Create structured technology trade-off analysis documents with scored comparison matrices. Use this skill whenever the user wants to compare technologies, evaluate architectural options, analyze build-vs-buy decisions, assess migration strategies, or produce any decision document that compares multiple approaches across weighted dimensions. Triggers on: 'trade-off analysis', 'tradeoff', 'comparison matrix', 'evaluate options', 'which technology should we use', 'compare approaches', 'pros and cons of', 'build vs buy', 'migration analysis', 'consolidation analysis', 'technology selection'. Also use when the user has completed technical research and wants to structure findings into a decision document.
Comprehensive framework for evaluating AI vendors and solutions to avoid costly mistakes. Use this skill when assessing AI vendor proposals, conducting due diligence, evaluating contracts, comparing vendors, or making build-vs-buy decisions. Helps identify red flags, assess pricing models, evaluate technical capabilities, and conduct structured vendor comparisons.
/cs:cto-review <plan> — Architecture and scaling interrogation. Tech debt, scaling cliffs, team scaling, build-vs-buy.
Guides customer-facing and internal technical solution design—discovery and requirements, integration and reference architecture, security/compliance fit, sizing and cost framing, RFP/RFI responses, PoC scoping, build-vs-buy, and handoff to delivery. Use when scoping a customer or partner solution, designing integration architecture for a deal, drafting RFP/RFI technical responses, planning a proof-of-concept, framing security and compliance fit, or preparing solution decks for stakeholders—not for org-wide landing zones and Well-Architected programs (cloud-architect, enterprise-cloud-architect), internal product ADRs and C4 (senior-system-architecture), production Terraform/IaC (infrastructure-engineer), hands-on cloud resource config (cloud-engineer), live PoC execution and competitive demos (sales-engineer), business strategy without technical design (business-consultant), contract redlines (commercial-counsel), or deep FinOps/GL (finops-analyst, compute-accounting-manager).
Plan and scope a Minimum Viable Product for a solopreneur. Use when deciding what to build first, what to cut, how to prioritize features, how to define "done" for a first launch, and how to structure the MVP build process. Covers the MVP definition, feature ruthless-cutting framework, build-vs-buy decisions, launch criteria, and post-launch learning loops. Trigger on "plan my MVP", "minimum viable product", "what should I build first", "scope my product", "MVP roadmap", "what features to include", "first version", "launch something".
Guides senior system and solution architecture—cross-service boundaries, integration patterns, non-functional requirements (scale, reliability, security, cost), ADRs, C4-style modeling, architecture review, build-vs-buy, and phased migration (strangler, dual-write). Use when designing multi-service systems, evaluating platform or vendor choices, writing or reviewing architecture decision records, defining standards and principles, or assessing technical risk across domains—not for single-service RFCs and module design (senior-software-engineer), data platform or mesh decisions (data-architect), cloud landing zone, Well-Architected, and migration architecture (cloud-architect), cloud/IaC implementation (infrastructure-engineer, cloud-engineer), internal developer platform product (platform-engineer), or program tracking (technical-program-manager). For business strategy and cases, use business-consultant; for applied AI (RAG, agents, copilots), use applied-ai-architect-commercial-enterprise.
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.
Guides management consulting-style work—engagement framing, hypothesis-driven problem structuring, issue trees, business cases, operating model and capability design, strategic options analysis, workshop facilitation, and executive recommendations (not legal advice). Use when diagnosing a business problem, structuring a strategy or transformation initiative, building a business case for leadership, designing target operating models, preparing steerCo or board recommendations, or advising on build-vs-buy and portfolio priorities—not for detailed requirements/BRDs (business-analyst), multi-team delivery tracking (technical-program-manager), contract negotiation (commercial-counsel), revenue accounting (senior-revenue-accountant), applied AI architecture (applied-ai-architect-commercial-enterprise), or system ADRs (senior-system-architecture). Canvas/TAM: business-model-researcher. Comms: communication-lead. M&A closing: transaction-manager. M&A principal/IC: transaction-principal.
Guides Claude from idea to working prototype using frameworks from OpenAI, Figma, and Airbnb. Use when starting new product features, planning MVP scope, making build-vs-buy decisions, or guiding users from concept to shippable prototype. Applies AI-first thinking (Kevin Weil), simplicity forcing functions (Dylan Field), and complete experience design (Brian Chesky).
Business case analysis with ROI, NPV, IRR, payback period, and TCO calculations for investment decisions. Use when building financial justification, cost-benefit analysis, build-vs-buy comparisons, or sensitivity analysis.