Hiring a fractional CTO in Austin: what to look for

I am based in Austin and I work as a fractional CTO for companies here and across the US. Founders in town ask me how to hire one, sometimes because they are considering me and sometimes because they are not and want a second opinion. This is the checklist I give them. It applies anywhere, with a few points that are specific to being in Austin.

Decide what you are hiring for first

Before you talk to anyone, write one paragraph about why. Not "we need a CTO" but the actual problem. The founder is making technical decisions they are not confident in. The team of eight has no technical executive and hiring has stalled. A raise is coming and diligence will look at the codebase. Production is unstable and nobody owns it. AI is everywhere in the team's work and nobody owns that either.

The paragraph determines what kind of person you need. Diligence and architecture problems need someone who has been through diligence and designed systems at scale. Org and delivery problems need someone who has actually run a team, not advised one. A founder who needs a peer needs someone who will disagree with them. If you cannot write the paragraph, start with a few advisory hours rather than an engagement, and let the paragraph emerge. I wrote about the different shapes in what a fractional CTO actually does.

Look for an operator, not a commentator

The fractional CTO market has a lot of people who have advised, spoken, and written about engineering leadership and comparatively few who have carried the pager. The difference shows up in the first month, when a real decision has to be made with incomplete information and someone has to own the outcome.

Ask what they have run. How many engineers, in what structure, for how long, with what results, and what went wrong. Someone who has led a 100-person org will have specific stories about the things that broke. Someone who has not will talk in frameworks. Both can be useful. Only one should be making your technical decisions.

Then ask what they have shipped recently with their own hands. A fractional CTO who cannot read your codebase is guessing about it. I build and run my own product with an agent stack and publish the telemetry on my now page, partly because I want to be able to answer this question with evidence rather than a claim.

The questions that separate candidates

A few questions I would ask any fractional CTO candidate, including me.

Walk me through your first three weeks here. The answer should be concrete: discovery of the architecture, team, delivery process and spend, a written 90-day plan with owners, then an operating cadence. If the answer is "it depends" with nothing after it, keep looking.

What would make you tell me I do not need you? A good fractional CTO will describe the situations where the right answer is a full-time hire, a VP of Engineering, or an agency. If they cannot imagine one, they are selling hours.

How do you work with a team on the days you are not here? You want to hear about written plans, visible metrics, a lead who runs the day to day, and clear rules for what waits and what does not. Mechanisms, not availability promises.

Tell me about a decision you got wrong at scale. Everyone who has operated has one. The useful part is what they changed afterward.

How do you handle AI in the engineering process? In 2026 this is not optional. You want someone who has installed review gates, testing rules, guardrails and spend controls for coding agents in a real team, and who can describe the failure modes, not just the upside. My approach is on the AI engineering leadership page.

Check references the right way

Ask for three references and make one of them an engineer who reported to the candidate, not just a founder or CEO they worked for. Founders will tell you whether the person was easy to work with and delivered. Engineers will tell you whether the person made the team better or just made the meetings longer.

Questions for the engineer reference: did the team ship more after this person arrived, did they understand the code, did they protect the team from thrash, and would you work for them again. Questions for the founder reference: did they tell you things you did not want to hear, did the plan they wrote in week two survive contact with reality, and how did the engagement end.

That last one matters. A clean handoff to a full-time leader is the best possible ending for a fractional engagement, and a candidate whose engagements only ever end badly is telling you something.

Red flags

A few things that should slow you down.

• No written proposal, or a proposal that is a number and a paragraph. Scope, cadence, decision rights, metrics and exit should all be in writing before work starts. More on that in how fractional CTO engagements are structured and priced.
• A long list of simultaneous clients. A fractional CTO can serve a few companies well. Past that, you are buying a slice of someone's attention that is already spoken for.
• Vagueness about hands-on work. If you want someone who reviews code and can ship, ask directly, and expect a direct answer.
• Pressure to take their preferred stack or their preferred vendors without a reason tied to your situation.
• Reluctance to be measured. The engagement should have numbers both sides look at when deciding to renew.

When local matters, and when it does not

Austin has a lot of companies that need this kind of help and a smaller number of people who have done the job at scale, so founders here often end up choosing between a local candidate and a remote one. Here is how I would think about it.

Local matters for the first few weeks, for planning sessions, and for the moments when the team needs to see the person in the room. Kickoff in person is better. Quarterly planning in person is better. A hard conversation with a lead is better over coffee than over video. If a remote candidate will not travel for those, that is a mark against.

Local does not matter for the weekly operating rhythm, code review, architecture decisions, or hiring loops. All of that works over video with a team that already works that way, and most Austin engineering teams do.

Time zone matters more than geography. A fractional CTO on Central Time overlaps with the whole US working day, and that is more useful than a shared zip code. I work remotely with teams across the country from Austin, and I come on site for kickoffs and planning when it helps.

The other local advantage is the network. Someone embedded in the Austin community can introduce you to engineers, other founders, and service providers who have been vetted by experience rather than by a search. That is a real benefit, and it is also the easiest one to overvalue. A great operator who is remote beats a well-connected local who has never run a team.

Structure the engagement so it can succeed

Once you have chosen, set it up properly. One to three days a week on a fixed schedule. A written 90-day plan by the end of week two. A weekly meeting with you, a weekly meeting with the team, and a dashboard you both look at. Clear decision rights: which calls the fractional CTO makes, which they recommend, which stay with you. A quarterly check on whether the shape still fits, including whether it is time to hire full time.

And give them the authority to change things. The most common reason a fractional engagement fails is a founder who wanted the title in the room but did not want anything to be different afterward.

If you want to talk to me

I keep a small number of engagements running at a time so each one gets real attention. The fractional CTO page describes how I work, my resume covers the background, from IBM through VP of Software Engineering at Talent Systems to the fractional work I do now, and the contact page is the fastest way to start. If after a conversation I think you need something other than a fractional CTO, I will say so.

Frequently asked questions

Does a fractional CTO need to be based in Austin to work with an Austin startup?

No. Weekly leadership, code review, architecture decisions and hiring all work remotely. In-person time helps for kickoff, quarterly planning and hard conversations, so look for someone who is local or will travel for those. Time zone overlap matters more than address.

What should I ask a fractional CTO candidate?

What they have run and what went wrong, what they have shipped recently with their own hands, what their first three weeks would look like, how the team operates on the days they are not there, how they handle AI coding agents in a real team, and what would make them tell you that you do not need them.

How many clients should a fractional CTO have at once?

A few. Enough that they bring pattern recognition across companies, few enough that each one gets real attention and a fixed schedule. Ask directly how many engagements they are running and how many days a week each one takes.

How do I know if a fractional CTO engagement is working?

By the end of 90 days you should have a written plan with owners, a weekly operating rhythm, visible metrics, releases on a schedule, a defined hiring plan, and the biggest technical risk being actively reduced. If you cannot point to those, ask why.