Hiring a Fractional CTO
11 posts on this topic — practical guidance from Shawn Livermore on fractional CTO, AI, and technology leadership.
The New Reasons Companies Hire a Fractional CTO in the AI Era
The traditional fractional CTO hiring triggers — team scaling, pre-IPO audit, technical co-founder departure — are still valid. They are no longer the only ones.
Read post →Why Fractional CTO Engagements Fail in the First 30 Days
Most fractional CTO failures are not competence problems. They are alignment problems that could have been resolved before the engagement started. Here is what those failures look like and what prevents them.
Read post →The Fractional CTO Evaluation Gap: Why the Candidate Who Interviews Well Is Often the Wrong Fit
Most companies evaluate fractional CTO candidates with full-time hiring criteria. The competencies that predict fractional success are meaningfully different — and the gap between the two is where most searches go wrong.
Read post →The Questions That Surface Implementation Leadership in a Fractional CTO Candidate
Most fractional CTO hiring processes ask about credentials and past projects. The questions that reveal whether a candidate can actually lead implementation inside your company are different — and most hiring managers don't ask them.
Read post →What Founders Get Wrong About the Fractional CTO Decision
Most founders reach for a fractional CTO too early or too late — and usually with the wrong problem statement. The decision becomes clearer once you know which gap you're actually trying to close.
Read post →Hiring a Fractional CTO in 2026: What the Role Covers That It Didn't Before
The fractional CTO role has expanded as AI agents take over more of the implementation work. Here is what the role covers now, what has stayed the same, and what to ask when hiring.
Read post →Hiring a Fractional CTO When Your Team Is Building With Agents
When Andrej Karpathy shifted to 80% agent coding, most responses focused on individual productivity. The more important implication is organizational: what does technical leadership mean when the engineering workflow has structurally changed?
Read post →Hiring a Fractional CTO in 2026: What the Interview Should Actually Test
The criteria for a good fractional CTO have shifted. What worked as an evaluation framework before agentic AI entered enterprise development leaves out the qualities that matter most now.
Read post →What Companies Get Wrong in the First 30 Days of a Fractional CTO Engagement
Most fractional CTO engagements that underperform weren't set up to succeed. The conditions that determine whether a fractional CTO can do their job are established by the company before the real work begins — and most companies get three of them wrong.
Read post →How to Evaluate a Fractional CTO Candidate Without Getting Burned
The fractional CTO market grew 47% in 2026. More supply means more variation in quality. Here is how to evaluate the candidates who will actually move your technology forward.
Read post →What to Look for in a Fractional CTO in the Vibe Coding Era
Vibe coding has changed what software teams do. The fractional CTO qualifications that mattered in 2022 are incomplete in 2026. Here is what to evaluate now.
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