Fractional CTO · Founder-led companies, $5M – $50M
You shouldn’t be the most technical person in the room.
Most founder-led companies outgrow the systems that got them here, and the bill shows up as growth you can’t take on, risk nobody has priced, and margin leaking through the gaps between tools. I own that problem so it stops being yours: what the technology is costing you today, what it caps you at, and what it takes to move the number.
The same problem, twice
Typical, $12M revenue
Systems nobody ownsIn sequence, owned
22 years
in technology leadership
$5M – $50M
the companies this is built for
Navy
before any of it
8 industries
shipped in, not just advised on
01 — Where this usually starts
None of these sound like a technology problem.
They’re what it sounds like from the inside. If you recognise three or more of these, the cause is almost never the thing being blamed for it.
- 01You are the most technical person in the room, and you shouldn't be.
- 02A board member or investor asks a technology question and you answer from memory, not from a number.
- 03Two reports answer the same question two different ways, and nobody can tell you which one is right.
- 04Technology spend goes up every quarter and nobody can tell you what the last increase bought.
- 05You know roughly when the current setup stops holding. Nobody has put a revenue number on it.
- 06Every tool works. None of them talk to each other.
- 07One person knows how the critical system works, and they just took a week off.
- 08Onboarding a new hire means teaching them the workarounds first.
02 — What’s actually happening
It’s not that your technology is bad. It’s that nobody owns it.
At $5M nobody needs to own the whole picture. Someone picks a tool, it works, everyone moves on. Do that for four or five years and you have a stack that was never designed — just accumulated. Each piece made sense on the day it was bought. Together they cost you margin, speed and accuracy, and no single person is responsible for that total.
So the questions land on you. Which CRM. Whether to rebuild. Whether that developer is any good. Whether the number in the dashboard is real. Those are executive technology decisions, and you are making them between everything else you do, without the context to make them quickly.
And it compounds the way debt does. Every shortcut taken to ship something faster was borrowed against future productivity, and you are paying the interest now — in slower delivery, higher maintenance, and people spending their week on work the system should be doing. Nobody sends you a statement for it.
That gap — real technology decisions, no technology executive — is the entire job.
03 — How the work gets framed
Every roadmap item lands in one of three buckets.
Not a project list. Three words that say what each piece of work is buying you, in language that survives being repeated to your board without you in the room.
Derisk
The things that can stop the business.
Single points of failure. One payment processor. One server. One person who knows how the critical system works. These rarely reach anyone's roadmap because nothing looks broken until the day it is, and by then the cost is not a technology cost.
Looks like The spreadsheet two people understand
Unclog
The things capping how fast you can grow.
Bottlenecks, manual re-keying, systems that do not talk, a backlog nobody has pruned in two years. Wherever a spreadsheet is bridging two tools, there is a constraint with a number attached to it, and that number is usually in labour.
Looks like Forty hours a month rebuilding one report
Scale
The things you need before the growth arrives.
Capacity, team capability, the systems that have to exist at three times this size. The point is to build them ahead of the revenue rather than during the quarter it shows up, because the second one costs multiples of the first.
Looks like The stack that caps out at $20M
04 — Plainly
What a fractional CTO actually is
A senior technology executive who runs your technology part-time and is accountable for the outcomes. Not a consultant who leaves a deck. Not a developer. The person whose name is on whether it worked.
A full-time CTO at this stage runs north of $300,000 plus equity, takes months to hire, and is more capacity than you need. The fractional version gives you the same seat for the days a month you actually need it. You are not buying hours. You are buying somebody senior being responsible for the result.
Concretely, that means
- Owning the technology roadmap and defending it
- Deciding what to build, buy, fix or kill
- Evaluating, developing and hiring the technical team
- Managing vendors and contracts, and cutting what isn’t earning
- Making the data reliable enough to run the business on
- Reporting to you and your board in numbers, quarterly
05 — The method
The Order of Operations
Nothing gets built until we know what's actually broken and what it's costing you.
- 01
Inventory
Weeks 1 – 2
Every system, contract, integration and line of technology spend, mapped in one place, with a dollar figure against each one. Who owns what. What breaks, how often, and who is the only person who can fix it. Most founders have never seen this on a single page, and the number at the bottom is usually larger than the one in the budget.
You get One page, one number, and where it is going
- 02
Sequence
Weeks 3 – 4
Every item sorted into derisk, unclog or scale, then ordered by what it does to revenue and risk — not by who asked loudest or which vendor called last. You get options rather than one path: the fast version, the cheap version, and the one I would actually run, each with what it costs and what it returns. Including the cost of doing nothing, which is the number most roadmaps leave out.
You get Three costed options and a recommendation, not a plan to accept
- 03
Execute
Ongoing
I own delivery. That means the roadmap, the vendors, the hiring, the standards your team works to, and the quarterly report that tells you what moved in the business — not what shipped. When something slips you hear it from me first, early, with the situation stated plainly, the options, and my recommendation. Bad news does not get softened or held until there is better news to pair it with.
You get Quarterly numbers you can hand to a board, and one name on them
06 — Ways to work together
Three ways in. Start wherever fits.
Fixed scope, fixed price
Technology Operating Review
For founders who want a straight answer before committing to anything.
Two weeks of asynchronous digging followed by a half-day working session with you and whoever else needs to be in the room. You come out with the inventory, the sequence and the costs — the first two phases of The Order of Operations, delivered as a standalone piece of work.
Monthly retainer
Fractional CTO
For companies where technology is now on the critical path to the next revenue milestone.
The engaged role. I own the technology roadmap and the business outcomes attached to it, work with your team on a normal weekly cadence, hire and manage the people and vendors who execute it, and report to you and your board each quarter in numbers they already use.
Lightest touch
Technology Advisor
For companies with a team that is shipping, but nobody senior setting direction.
Every other week with you, your technical lead, or both. Enough to keep the roadmap honest, pressure-test the decisions that are expensive to reverse, and give the person running your team someone to think out loud with. You are paying for a strong opinion, so you get one.
08 — Where it’s been done
- Insurance & agency distribution
- Home services & specialty contractors
- Solar & energy services
- Sales organizations
- Real estate operations
- SaaS & vertical platforms
- PE-backed rollups
The industry changes. The pattern doesn’t: a company that grew past its systems, and no one senior whose job is the whole picture.
Get the technology expertise you need to grow.
Fifteen minutes, no pitch. Tell me what’s going on and I’ll tell you whether this is something I can help with, something you can fix internally, or something you can safely ignore for another year. You’ll leave with at least one useful answer either way.