About
Technology decisions shouldn’t be the hardest part of running your company.
For most founder-led businesses between $5M and $50M, they are. Not because the technology is exotic, but because there’s nobody in the building whose job is the whole picture. That’s the job I take.
Anthony Ricciardo — Fractional CTOLinkedIn ↗
The short version
My background is unusual for this work. I spent years in the Navy before I built technology companies, and that order matters. The Navy teaches you to think about systems the way an operator does: what breaks under pressure, what actually scales, and what is an expensive distraction dressed up as progress. I have never stopped evaluating technology that way.
Twenty-two years in, most of my work sits in two places. Insurance and agency distribution, where I’m licensed in fifteen states, have run the sales floor myself, and built the AI dialer that fed it — so when I talk about lead-to-close economics it isn’t theory. And home services and specialty contractors — pool, landscape, solar, roofing — where the systems mess is usually costing more than anyone has stopped to measure.
Around that: AI-powered sales platforms, consumer marketplaces with native mobile apps, and the data infrastructure companies in real estate, solar and SaaS run on. The through line is sales organizations, where the gap between what the CRM says and what is actually true is usually the most expensive thing in the business.
The common thread is not an industry. It’s a moment: a business growing faster than its technology can support, and the work of getting those two back in sync before the gap starts costing customers.
What I am not is a vendor. A vendor is hired to deliver a scope and is finished when the scope is met, which is why a vendor will never tell you the scope was wrong. I’d rather be the person in the room who asks why before how, brings you options instead of one path, and is measured on whether the business moved — not on whether the thing shipped.
The work is closer to installing sprinklers than to firefighting. Anyone can put out the fire in front of you this week; the job is building systems that stop starting them, so that in a year the technology is running quietly and you are spending your week on the business instead. If you’re spending too much of yours on technology decisions and not enough on growth, that’s the conversation I like having.
What it’s like to work together
Five things you can hold me to.
One person is accountable
Not a pod, not a partner who sold it and an associate who runs it. If the roadmap slips you hear it from me, before you hear it from a dashboard, with what it costs and what I recommend doing about it.
Your team gets better, not replaced
Most technical teams at this stage are not underperforming — they are unmanaged and pointed at the wrong things. I would rather develop the people you have than run a hiring cycle you didn't need. When a hire is genuinely required, I make the case with numbers.
Every recommendation carries a cost and a consequence
Including the option of doing nothing. You get options with the trade-offs shown — the fast one, the cheap one, and the one I would actually run — and then a recommendation. You should never be asked to approve something you can't explain to a partner or a board afterwards.
You will get pushed back on
When you tell me to build something, my first question is why, and I ask it because I want the outcome you're after rather than the thing you asked for. Sometimes the answer is that you were right. Sometimes it's that the thing isn't worth building. You are not paying me to agree with you — the opinion is the product, and a fractional CTO who never says no is an expensive pair of hands.
You can end it
No annual lock-in on the retainer. If the work isn't earning its keep you should be able to stop it in thirty days, and the roadmap and documentation are yours to keep either way.
Industries shipped in
- Insurance & agency distribution
- Home services & specialty contractors
- Solar & energy services
- Sales organizations
- Real estate operations
- SaaS & vertical platforms
- PE-backed rollups
Worth a conversation?
Fifteen minutes. Tell me what’s going on with your technology and I’ll give you a straight read on it — including if the answer is that you don’t need someone like me yet.