Interim & Fractional CTO
Your CTO just resigned. Don't post the job yet.
I’ve stepped in as interim CTO seven times, most often at companies owned by private equity, usually with a clock running. I steady the technology organization, hand over to the right permanent leader, and then I leave.
It usually starts with a phone call. A CEO, a little out of breath. The technology leader has just resigned, there's a board meeting coming, and somewhere in the first ten minutes I hear some version of this: I've never really understood how that part of my company works.
The job is to steady the technology organization, hand over to the right permanent leader, and leave. The CEO expects me to start with the technology. The first problems are almost always upstream of it: in the process, and then in the people.
When your technology leader leaves, the questions about the technology stay with you, and the interim leader you'd most like to keep is the one you have to let go.
Four questions for this week
Most CEOs can't answer these on the day their technology leader resigns. Start here.
What does your CTO do all day? A title won't tell you.
Who can release code without them? Find out who holds the keys.
Who would follow them out the door? Check before you guess.
If they left today, what stops? Ask them. Most have never been asked.
The first hundred days
One page, three columns. You see it before you hire me, and the word technology isn't at the top of any of them.
Days 1–30
Listen and map
I sit down with every person in engineering and product, one at a time, and get the whole team in one room for two days. A short weekly check-in starts. We map the systems: what you have, what's fragile, and who understands each piece.
You get: the real problem, in time to write the job description for it.
Days 31–60
Choose and start
We pick the handful of fixes that matter and protect the people doing them: focus blocks, fewer meetings. The team gets a week to build what they've been dying to build. Anything that needs money gets a short case with a date, a measure and a sponsor.
You get: fixes under way, each with a name on it.
Days 61–100
Deliver and hand over
The fixes keep moving. We design the permanent role, hire the permanent leader, and onboard them properly before I go.
You get: a permanent leader in the chair, set up to succeed.
I pitch every engagement as a hundred days. About half the time it has been extended for a second hundred, and it rarely runs to a third.
The technology comes third
Process comes first, because it's the one thing a team will tell a newcomer about right away. A team will defend a teammate who's falling behind, and it will defend its technology choices too. Nobody holds back on where the process breaks: the slow handoff, the meeting that decides nothing, the work that sits for a week waiting on somebody else.
Then people: who's in the wrong seat, and which roles are missing. Then the technology, and by then most of the technology decisions follow from the first two.
Third still means this quarter. Monitoring, a tested backup and security don't wait for the next leader to start.
Why I tell you when I'm leaving
Everybody in the building knows I'm leaving, so they tell me things. I don't decide anybody's raise, their bonus, or whether they have a future there, so telling me the truth costs them less than telling you. Everything they tell me goes into the handover, and the permanent leader lands on solid ground.
I have one loyalty, and it's to the work. That's why I can tell your board something you don't want them to hear, and why it helps you.
About six weeks in, things will be calmer, the team will be talking to you again, and you'll want me to stay. You'll offer me the job. I'll say no, and you'll be angry for about a week. Don't hire anyone that week.
What you and your board see every Friday
The update. A few pages to you and your operating partner every week, whether or not anyone asks. Every number in it is a link to the system it came from.
The same measures. Better, faster and cheaper, with revenue on the bottom: keep the customers you have, win the ones you don't. No measure comes off the page because it looks bad.
The check-in. A short weekly form, anonymous unless you choose to sign it: how is your team, how are you, and where did your week go. One bar for every Friday, the trailing thirteen weeks, never rolled up.
The contract page. Every commitment I made, graded by me, in front of your board. Gray means built. Green means verified working. Shipped isn't the same as working.
The handoff is the whole job
Give me thirty to forty-five days before you open the search. If you post the job Monday, you'll write the job description for the problem you think you have. Give me a month, and you'll write it for the one you've got.
Then we design the role, and every finalist is scored on one sheet with two totals: the overall score, and the score without the personal questions. The first number tells you who you liked. The second tells you who can do the job. Hire the person who wins on both.
A new permanent CTO usually burns their first 60–90 days just finding the landmines: the personnel situations, the political dynamics, the people who'll resist whoever comes next. I find them during the engagement and either defuse them or hand over a map. I write the successor's onboarding plan, a full quarter of it, and stay available to them for sixty days after I go.
You'll know it worked when you stop needing me. Usually about a week before you notice.
Seven times interim CTO. Every engagement ended with a permanent leader in place.
The exit clause
Most interim contracts I've seen spell out what the interim leader will do and say nothing about how they leave. These four lines do. Every line binds the interim CTO. Read from the CEO's chair, every line also guards you against something you'll want to do.
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The engagement runs one hundred days. It can be extended once, for up to another hundred, if a permanent leader has not yet been hired and onboarded. It ends when that leader is in place, and no later than day 200.
Guards against keeping the rescuer forever
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The interim CTO will end the engagement early, on two weeks' notice, if he is asked to keep material information from the board.
Guards against hiding the bad news
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The interim CTO will not accept a permanent role with the Company. If he is asked to stay after he has declined once, he may end the engagement early on the same notice.
Guards against converting the rescuer
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Before he leaves, the interim CTO writes the successor's onboarding plan, and stays available to the successor for sixty days after.
Guards against rushing the successor
Coming December 2026
The Exit Clause
A Leadership Fable About What to Do When Your CTO Leaves
Neil Hartman runs a $40 million software company owned by private equity, with a sale on the horizon. On a frozen Friday afternoon, his CTO of eleven years closes the office door and says he's leaving. Then comes Cole Bennett, an interim CTO who puts technology third on his own plan, grades himself in front of the board every week, and writes his own exit clause before he starts.
It's told from the CEO's chair, for CEOs, operating partners and deal teams, and the working documents are in the back: the exit clause, the hundred-day plan, the board pages, the hiring rubric and the onboarding plans.
I also speak on this: When the CTO Leaves.
Common questions
Interim, fractional, or permanent: what are you?
Interim, full-time or part-time. Interim is the job: a fixed term through a leadership gap that ends with a permanent leader in place. Fractional only says how many days a week. I'm not the permanent answer; I find that person and set them up to succeed.
How long does an engagement run?
I pitch a hundred days. About half the time it has been extended for a second hundred, and it rarely runs to a third.
What would make you walk away?
Two things. If you hide something from your board, I'm out: I report to you, and I don't lie to the people who own the company. And if you ask me to stay past the handover. I'll say no the first time, and if you keep asking, I'll leave early. It's the only way I know to make the handover work.
What happens to the leader who's leaving?
I want them to leave well. My job is to make sure nobody has to call them at midnight after they've gone, so I take things off their plate until they have nothing left to do. Where it fits, I'll ask you to keep them on a short retainer. Making them an ally costs far less than the alternative.
Do you write code, or just advise?
Both. I make the calls (who builds what, what stops), and I'm in the codebase alongside the team. AI changed what one experienced leader can do hands-on, and I got back to building about eighteen months ago.
Where does AI fit?
Agents read your history, sort your tickets and draft tests, and a person checks what they find. No agent touches production, and everything an agent writes, a person reads. If AI use goes up and rework goes up with it, slow down.
I'm an operating partner. What should I ask in the first week?
Ask when the search opens, and if the answer is Monday, ask what problem the job description will describe. Ask how the interim CTO's contract says they leave. Ask who will answer the board's technology questions until the new leader can, and who decides what gets built.
What does "done" look like?
The situation is stable, the team has momentum, and your successor has context, relationships, and a defused set of landmines. Then I leave.