Fractional CTO · $5M – $50M

Go back to running the company.

Nothing gets built until we know what's actually broken and what it's costing you. You get the inventory, the costed options, and one name accountable for the number at the bottom — reported in revenue, cost and risk, not in what shipped.

Anthony Ricciardo, Fractional CTO
  • 22 yearsin technology leadership
  • $5M – $50Mthe companies this is built for
  • Navybefore any of it
  • 8 industriesshipped in, not just advised on

The symptoms

If two of these are true, the setup has already been outgrown.

Not a diagnostic. These are the sentences founders say on a call before they know what to call the problem.

  • You are the most technical person in the room, and you shouldn't be.
  • A board member or investor asks a technology question and you answer from memory, not from a number.
  • Two reports answer the same question two different ways, and nobody can tell you which one is right.
  • Technology spend goes up every quarter and nobody can tell you what the last increase bought.
  • You know roughly when the current setup stops holding. Nobody has put a revenue number on it.
  • Every tool works. None of them talk to each other.
  • One person knows how the critical system works, and they just took a week off.
  • Onboarding a new hire means teaching them the workarounds first.

What changes

Predictable beats cheap.

Technology spend that moves unpredictably is not a budgeting problem, it is a visibility problem. The line does not need to go down so much as it needs to stop surprising you.

Technology spend · before and after

UnmanagedAfter the review

Illustrative, not a client result. Real figures go here when there are real figures.

The Order of Operations

  • 01 Inventory
  • 02 Sequence
  • 03 Execute

01 · Weeks 1 – 2

Inventory

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.

One page, one number, and where it is going

02 · Weeks 3 – 4

Sequence

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.

Three costed options and a recommendation, not a plan to accept

03 · Ongoing

Execute

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.

Quarterly numbers you can hand to a board, and one name on them

The output vocabulary

Every item lands in one of three buckets.

Three words a founder can repeat to a board member who was not on the call. That is the actual test.

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.

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.

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.

The stack that caps out at $20M

Engagements

Three ways in, defined by who they are for.

Not by feature list. You should be able to tell which one is yours at a glance.

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.

  • Full map of systems, spend and ownership, with a dollar figure on each
  • Everything sorted into derisk, unclog and scale
  • Three costed ways to sequence it, and the one I would run
  • What it costs you to do nothing for four more quarters
  • Yours to keep and execute with or without me

Fixed scope, fixed price

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.

  • Accountable for business outcomes, not for delivering a scope
  • Roadmap owned, maintained and defended in front of whoever disagrees
  • Your team evaluated, developed and, where needed, hired
  • Quarterly reporting in revenue, cost and risk — not features shipped
  • Sprinklers, not firefighters: the goal is systems that stop needing me

Monthly retainer

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.

  • Biweekly working sessions
  • Expensive-to-reverse decisions reviewed before they're made, with options
  • A second opinion on hires before you make them
  • Somebody who will tell you the plan is wrong while it is still cheap

Lightest touch

Built for

Insurance & agency distributionHome services & specialty contractorsSolar & energy servicesSales organizationsReal estate operationsSaaS & vertical platformsPE-backed rollups

Next step

One call. A straight answer about what is actually broken.

No pitch deck. If the honest answer is that you do not need this yet, that is the answer you get.