Portfolio Turnaround CTO

A turnaround CTO for the companies you've bet on.

When a portfolio company is burning too much and shipping too little, the value-creation plan stalls and the hold clock keeps running. I step in as a turnaround CTO for PE and VC portfolio companies: full-time in the seat, aggressively taking cost out of the technology function while rebuilding it into a top-tier, AI-driven work environment. The company comes out leaner and faster, and then I hand off and go.

PE & VC portfoliosCosts down fastAI-driven by defaultOne operator, no bench
Oshri Cohen, turnaround CTO for portfolio companies
Oshri CohenFractional & Interim CTO
The short answer

What is a turnaround CTO for portfolio companies?

A turnaround CTO for portfolio companies is a senior technology executive who takes over a PE- or VC-backed company's technology function full-time with a blunt mandate: get the cost base down, get delivery up, and make both show in the numbers the fund reports on. The lever that makes both possible at once is AI. A top-tier AI-driven work environment, agents and copilots wired into how the team builds, tests, ships and supports, lets a leaner organization outship the bloated one it replaces.

This is not a caretaker interim role. Cost reduction here is aggressive and early: cloud spend, vendor sprawl, duplicated tooling, org shape. But cutting is only half the mandate. Every dollar removed is matched against a rebuild plan, so the board never has to choose between a cheaper function and a faster one. They get both, and they can watch it happen in the delivery metrics.

Most firms searching for this kind of operator are choosing between a consulting bench and a person. I'm the second kind. There's no firm behind me and no account manager between us. The operator you evaluate is the operator who shows up, and the same one who answers to your operating partner when something slips. The work is mostly remote, from Eastern Time, for US portfolio companies.

Also known as: portfolio company turnaround CTO, PE turnaround CTO, cost-reduction CTO, interim CTO for portfolio companies. See also the general turnaround CTO and temporary CTO pages.

When funds call me

Three moments this mandate exists for.

Different deals, same shape: the burn is eating the thesis and nobody senior owns fixing it.

The cost base ate the plan

Engineering spend grew faster than revenue: cloud bills nobody owns, vendors nobody remembers buying, headcount shaped for a roadmap that no longer exists. The model assumed margin that isn't there.

Slow and expensive at once

The worst combination. Releases take months, the burn is climbing anyway, and the board deck keeps getting vaguer. More money is clearly not the answer, and nobody inside can say what is.

The AI story is still a slide

The investment committee priced AI-driven efficiency into the deal. A year later it's a pilot and a paragraph. Someone has to actually build the AI-driven operating model the thesis assumed.

How I work

Find the money. Rebuild the machine. Hand off.

First

Find the money

  • Read the thesis, the model and the 100-day plan with the deal team
  • Audit the full cost base: cloud, vendors, tooling, org shape, contractors
  • Steady the team and keep shipping while I map what's actually there
Then

Cut and rebuild

  • Take cost out aggressively, sequenced so delivery never stalls
  • Stand up the AI-driven work environment: agents and copilots across the SDLC, support and internal ops
  • Report in fund language: run-rate saved, EBITDA impact, DORA trend
Finally

Hand off

  • Help define, evaluate and land the permanent CTO for the leaner org
  • Document the architecture, the cuts, the decisions and the plan
  • Stay reachable to the fund for the next company that needs this
Shapes of the work

Four ways funds use me.

Scoped to the deal in front of you, not to a retainer.

Cost

Cost-base reset

A bounded mandate to take the technology run-rate down hard: cloud, vendors, tooling, org shape. Every cut is matched with the automation or AI leverage that absorbs the work.

Rebuild

AI-driven work environment

I rebuild how the company builds: agents and copilots wired into engineering, support and internal ops, so a leaner team ships more than the bigger one did. Measured with DORA, visible to the board.

Exit

Pre-exit hardening

Twelve to eighteen months out, I get the cost story and the technology story ready for the buyer's diligence: clean run-rate, documented systems, metrics that survive scrutiny.

Portfolio

On call across the fund

Some firms keep me as their first call. Each engagement is one company at a time, but the playbook and the context carry over, and every run gets faster.

Measured in outcomes

A track record, not a pitch.

30+
Companies served as fractional & interim CTO since 2018
Low → Elite
DORA delivery performance, in 90 days
12
Engineering teams led across 7 countries
25yrs
In software; 20 in technology leadership

Cost-cutting that leaves a slower company isn't a turnaround, it's a write-down in installments. The point is a leaner function that ships more than it did before the cuts, because AI carries the load.

Oshri Cohen
Common questions

What operating partners ask.

What does a turnaround CTO for portfolio companies actually do?

Two things at once: aggressively reduce the technology cost base, and rebuild the function into an AI-driven work environment so output goes up while spend goes down. I run technology full-time while it happens: strategy, delivery, the team, vendors, board reporting. The engagement ends when the run-rate and the delivery metrics both hold without me.

Where does the cost reduction actually come from?

The usual suspects, found systematically: cloud spend nobody right-sized, overlapping vendors and tooling, contractors that outlived their project, and an org shaped for a roadmap that changed. The biggest lever is AI leverage, because when agents and copilots carry real work, the function needs fewer hands to ship more.

Will cutting costs slow the roadmap down?

Done naively, yes, and that's the classic failure. It's why the cuts and the AI-driven rebuild happen together: every dollar removed is matched against the automation that absorbs the work. Delivery is measured with DORA metrics from week one, so if the trend dips, the board sees it and so do I.

What does a top-tier AI-driven work environment mean concretely?

AI as the default in how work gets done, not a pilot on the side. Coding agents and copilots in the development loop, AI in testing, code review, support and internal operations, and an operating model rebuilt around them. The result is a leaner team with the throughput of a much larger one, and delivery metrics that prove it.

Do you work for the fund or for the company?

Both, and I keep one version of the truth. The company gets a full-time operator who leads the team through a hard chapter like a real executive. The fund gets honest reporting in deal language: run-rate saved, risk retired, dates held. Either side can be the paying client; the reporting is the same.

Are you a firm with a bench of CTOs?

No, and that's deliberate. The person you diligence is the person who shows up, and the accountability never diffuses into an account team. One operator, directly engaged, gone when the job is done.

How quickly can you start?

Fast. These situations are urgent by nature, a burn problem or a stalled plan, so I move in days, not months, and the role gets full-time attention from day one.

Burning too much,
shipping too little?

If a portfolio company's cost base is eating the thesis, the conversation costs you thirty minutes.