cto-advisor

Provide CTO-level strategic guidance for engineering leadership and organizational decisions.

8|1|Updated Feb 27, 2026
One-click install
npx skills add https://github.com/thesaifalitai/claude-setup --skill cto-advisor-thesaifalitai
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: cto-advisor
Source: https://github.com/thesaifalitai/claude-setup/tree/main/skills/cto-advisor
Command: npx skills add https://github.com/thesaifalitai/claude-setup --skill cto-advisor-thesaifalitai

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

Provides experienced CTO and VP-level guidance to help engineering leaders make strategic, organizational, and product-technology decisions without getting lost in implementation details.

Core Features & Use Cases

  • Technology strategy & tech radar: Recommend adopt/trial/assess/hold guidance for stack choices and platform direction.
  • Roadmap planning & OKRs: Create engineering roadmaps, objective key results, and horizon-based planning for short and long term.
  • Build vs Buy & vendor evaluation: Structured templates to evaluate vendors, cost tradeoffs, and lock-in risk.
  • Technical debt triage & DORA metrics: Classify debt, define servicing rules, and benchmark deployment frequency, MTTR, and change failure rates.
  • Team structure & hiring: Hiring scorecards, team topologies, first 90 days playbook for new CTOs or tech leads, and blameless postmortem culture guidance.
  • Use Case: Rapidly onboard a new CTO to assess current engineering health, prioritize top technical bets, and deliver a 90-day execution plan.

Quick Start

Advise on a 90-day engineering roadmap and hiring plan for a Series A startup scaling from 10 to 50 engineers.

Frequently Asked Questions about cto-advisor

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I create a first 90 days plan for a new CTO at a startup?▼

To create a first 90 days plan for a new CTO, assess current engineering health, prioritize top technical bets, and use a structured playbook to deliver execution plans for team structure, hiring, and roadmap planning.

What is the best way to triage technical debt using DORA metrics?▼

Triage technical debt by classifying it into categories, defining clear servicing rules, and benchmarking DORA metrics like deployment frequency, MTTR, and change failure rates to prioritize remediation efforts.

How do I evaluate build vs buy decisions for engineering platform vendors?▼

Evaluate build vs buy decisions using structured templates to assess vendor cost tradeoffs, platform lock-in risks, and technology strategy alignment to ensure evidence-based vendor selection.

Can I generate engineering OKRs and roadmap planning frameworks for scaling teams?▼

Yes, you can generate engineering OKRs and roadmap planning frameworks by applying horizon-based planning techniques to define objective key results for both short and long-term team scaling goals.

How do you structure team topologies and hiring scorecards for a Series A startup?▼

Structure team topologies and hiring scorecards for a Series A startup by defining team boundaries, establishing blameless postmortem culture, and creating standardized scorecards to scale engineering teams effectively.

When do I need a tech radar for stack choices and platform direction?▼

You need a tech radar for stack choices when defining platform direction, allowing you to systematically categorize technologies into adopt, trial, assess, or hold statuses to guide engineering strategy.