The 90-Day Fractional CTO Checklist

Day 1 Is Already Late

By the time a company hires a fractional CTO, something is already on fire. The first 90 days aren't about "getting up to speed" — they're about delivering tangible results while building the foundation for everything that follows.

Week 1–2: The Audit

What You're Looking For

Before you can fix anything, you need to understand the current state:

• Architecture review — draw the system as it actually is, not as the docs say
• Deployment pipeline — how does code get to production? How long does it take?
• Incident history — what's broken in the last 90 days? What's the MTTR?
• Team structure — who owns what? Where are the bottlenecks?
• Technical debt inventory — what's slowing the team down daily?

The Output

A single document: "State of Engineering" that covers:

1. What's working well (yes, start here)
2. The top 3 risks to the business
3. Quick wins that can be shipped this month
4. A 90-day roadmap with clear milestones

The goal isn't to be comprehensive. It's to be actionable.

Week 3–4: Quick Wins

Ship something visible in the first month. This builds trust and momentum:

• Fix the flaky CI pipeline that wastes 2 hours/day
• Set up proper staging environments
• Implement basic monitoring and alerting
• Clear the security vulnerability backlog
• Document the deployment process

# Example: Basic health check + uptime monitoring
curl -s https://api.yourapp.com/health | jq .
 
# Set up a simple alert
if [ $(curl -s -o /dev/null -w "%{http_code}" https://api.yourapp.com/health) != "200" ]; then
  notify-team "API health check failed"
fi

Month 2: Foundation

Process Without Bureaucracy

• Sprint cadence — 2-week sprints, async standups, one planning session
• PR reviews — every PR reviewed within 4 hours, max 400 lines
• On-call rotation — shared responsibility, documented runbooks
• Architecture Decision Records — lightweight docs for big decisions

Technical Foundation

• Establish coding standards (automate with linters, not meetings)
• Set up error tracking (Sentry, not "check the logs")
• Implement feature flags for safe deployments
• Create a proper local development environment

Month 3: Velocity

By month 3, the team should be noticeably faster:

What "Done" Looks Like

At the end of 90 days, the company should have:

1. A clear technical roadmap aligned with business goals
2. A team that ships with confidence
3. Monitoring that catches problems before customers do
4. A hiring plan (if needed) with clear role definitions
5. Documentation that lets the next person succeed

The Anti-Patterns

Things a fractional CTO should never do in the first 90 days:

• Rewrite the entire system
• Introduce a new programming language
• Hire 5 engineers before understanding the work
• Build internal tools before shipping customer features
• Optimize for scale you don't have

The Real Deliverable

The best fractional CTOs make themselves unnecessary. The 90-day goal isn't to become indispensable — it's to build systems and processes that work without you.

That's the job.