Fractional CTO & VP Engineering Services

You have raised your round. The board wants a roadmap, your engineers want direction, and the architecture decisions you make in the next six months will either compound or haunt you. What you need is executive judgment — not necessarily forty hours a week of it.

That is the gap I fill.

How I engage

Fractional CTO

For companies with no technology executive, or a founding engineer who has outgrown the role.

I own the technical strategy end to end: the roadmap, the architecture, the build-versus-buy calls, the vendor relationships, and the story you tell investors about your technology. I sit in your leadership meetings and I am accountable for engineering outcomes, not just advice.

Typical shape: one to three days a week, three months minimum, reviewed quarterly.

Fractional VP Engineering

For companies where the technical vision is clear but delivery is not.

This is the execution seat: team structure, hiring plans, performance management, the SDLC, CI/CD, and the operating cadence that turns a roadmap into shipped software. I have taken a team from one release per quarter to multiple releases per week by rebuilding exactly these things.

Typical shape: two to three days a week, six months minimum.

Diligence & compliance readiness

For companies raising, selling, or entering a regulated market.

Architecture review, security and compliance posture, engineering team assessment, and the remediation plan to close the gaps — before someone else finds them. I have led SOC 2 Type II, PCI DSS, HIPAA, HITRUST, and GDPR programmes, and I have sat on both sides of an acquisition table.

Typical shape: a four-to-six week engagement, or ongoing advisory.

What the first 90 days look like

Every engagement starts the same way, because you cannot fix what you have not seen.

Days 1–14 — Listen and assess. I talk to every engineer, your product leadership, and your most frustrated customer-facing colleague. I read the code, the incidents, the backlog, and the last two quarters of delivery history. You get a written assessment: what is actually true, what is at risk, and what I would change first.

Days 15–45 — Stabilise. We fix the thing that is bleeding. Usually that is delivery cadence, an architecture decision that is blocking three other decisions, or a compliance gap with a deadline attached. This is where you should start feeling the difference.

Days 46–90 — Build the machine. Team structure, hiring plan, technical roadmap tied to your business milestones, and the operating rhythm that keeps it on track after I step back. The goal is that the improvement survives my departure.

By day 90 you should have a roadmap your board understands, an engineering team that knows what it is building, and a clear-eyed view of what you need from a permanent CTO — including whether you need one yet.

Who this works for

This is a good fit if you are a Series A or B company in Healthcare Tech or FinTech, somewhere between five and fifty engineers, and you have real revenue or real funding behind you.

It is a poor fit if you are pre-seed and need someone to write the first version of the product, or if you want a contractor to execute a plan that is already settled. I am most useful where the hard part is judgment, not hands.

Why me

I have been doing this for twenty-five years, and I have seen this movie before — in 1998, in 2008, and in 2018.

I built my first systems as the sole employee of an ISP that went from 100 to 3,000 customers in eighteen months. I spent thirteen years at Rackspace as it became a cloud company, running product for Cloud Identity and helping launch Barbican as an official OpenStack project. I led engineering at ClearDATA building HIPAA-compliant infrastructure, ran global DevOps and compliance at Chargify through its acquisition by Battery Ventures, unified four acquired brands into one product organisation at CyberFortress, and reported to the CEO at SWIVEL through a reorganisation and an acquisition.

That range matters because your problem is rarely purely technical. It is usually a technical problem wearing an organisational costume.

Frequently asked questions

What does a fractional CTO actually do? A fractional CTO provides executive-level technology leadership part-time: the technical strategy, architecture decisions, engineering org design, and hiring plan a full-time CTO would own — at the fraction of capacity your stage actually needs. For most Series A and B companies that is one to three days a week.

How does the cost compare to a full-time hire? A full-time CTO at Series A or B typically costs $250,000–$400,000 plus meaningful equity. A fractional engagement is a fraction of that, and carries no severance risk if your needs change.

When should I hire fractional instead of full-time? When you need executive judgment more than executive hours. If you need forty hours a week of hands-on architecture, hire full-time — and I will happily help you find and evaluate that person.

Do you work remotely? Yes. I am based in San Antonio, Texas and work with teams across the United States and Mexico, travelling on-site for planning sessions and key milestones.