Troy A. Smith, Fractional CTO Blog

The First 90 Days: What to Expect When You Hire a Fractional CTO

Hiring a Fractional CTO is a smart, flexible way for startups and SMBs to gain executive-level tech leadership without committing to a full-time salary. But what actually happens once they join? The first 90 days are critical to setting the tone, identifying priorities, and charting a scalable path forward. This post breaks down what you can expect when you bring a Fractional CTO onboard—and how to make the most of their early engagement.

Phase 1: Discovery & Audit
(Weeks 1–3)

Objective: Understand your business, people, and technology.

In the first few weeks, your Fractional CTO will hit the ground listening. Their goal is to gather context fast and identify both immediate risks and long-term opportunities. Expect them to:

• Review existing systems, tools, codebases, and documentation
• Interview stakeholders (founders, product leads, developers, etc.)
• Evaluate current product roadmap and technical debt
• Assess team structure and skill gaps
• Understand business objectives, customer needs, and constraints

Outcome:
A clear understanding of where things stand and a prioritized list of risks and opportunities.

Phase 2: Strategy & Roadmap
(Weeks 4–6)

Objective: Align technology direction with business goals.

With the audit complete, the CTO moves into planning mode. During this phase, they’ll define a strategy that connects your tech stack to your business growth goals. Expect deliverables like:

• A high-level technology roadmap for the next 6–12 months
• Recommendations for architecture, security, DevOps, or automation improvements
• A hiring or team optimization plan (if needed)
• A shortlist of urgent fixes or high-ROI opportunities

Outcome:
A focused plan of action with buy-in from stakeholders and clarity on who’s doing what.

Phase 3: Execution & Leadership
(Weeks 7–12)

Objective: Deliver wins and build momentum.

Now it’s time to get things done. Your Fractional CTO will often act as both strategist and operator, working hands-on with your dev team or external vendors. Expect them to:

• Lead or oversee implementation of the roadmap
• Drive agile practices or team rituals (standups, sprints, etc.)
• Set up KPIs or metrics for tracking performance
• Provide coaching, recruiting help, or process refinement
• Communicate progress clearly with leadership

Outcome:
Measurable progress, stronger team alignment, and increased confidence in your tech direction.

What Founders Can Do to Maximize Value

To get the most out of the first 90 days, here’s how you can set your Fractional CTO up for success:

✅ Be transparent — Share the good, the bad, and the ugly.
✅ Clarify business goals — Revenue, product-market fit, customer feedback—whatever matters most.
✅ Create access — Give them time with your key people and systems.
✅ Support change — Let them lead through influence, even if it means shifting gears.

Conclusion

The first 90 days with a Fractional CTO can unlock tremendous value—fast. From uncovering hidden risks to creating scalable roadmaps and inspiring your team, they serve as the catalyst your business needs to move forward with confidence.

Whether you’re prepping for a product launch, scaling your team, or cleaning up years of technical debt, a seasoned Fractional CTO can help you get there—without the overhead of a full-time hire.