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.