I'm an executive CIO. I embed with leadership teams, design and build the systems that let a company scale, and apply agentic AI where it moves a real number. I operate inside the business — in the meetings, the decisions, and the work that actually ships.
Not a consultant. Not a vendor. I join leadership teams — usually fractional or interim, occasionally full-time for a window — and own the decisions that get made. The people are always more important than the systems, so I'm in the meetings, the standups, and the hard conversations.
I've been the CEO. I've been the COO. I've led the people, given the advice, and made the call when someone had to. What the work looks like depends on the business: unblocking what's slowing it down, turning data into signals the team can act on, cutting the software stack down to what actually earns its keep, and giving the CEO a straight read on the operation.
Most companies don't need bespoke tools for everything — but when there's a workflow, a data problem, or a decision loop that off-the-shelf can't handle, that's where I step in. Agentic workflows, document pipelines, reporting copilots, and back-office automation — each pointed at a real business outcome.
In a role like this the people matter more than the systems.I'm in the meetings, the standups, the hard conversations — operating inside the business, not writing decks about it from the outside.
Serving clients across the United States.
LLMs are plumbing now. The edge is in the workflow design — where a human hands off, what the agent is allowed to decide, and how the output gets evaluated. That's the work.
Every piece of software now claims to have AI. Every vendor has a copilot. Most companies end up with five disconnected pilots, someone using ChatGPT, someone else using Claude, no policy, no integration, and no measurable outcome. The technology isn't the hard part anymore — knowing why you're deploying it, and what you're choosing not to build, is.
When AI shows up inside a company without a strategy, it shows up as shadow IT. Employees paste customer data into free tools. An automation gets built against a production database with no permission scoping. A chatbot leaks an internal doc. The risk isn't hypothetical — it's already happening in most orgs. Integrating AI properly means the same discipline you'd apply to any critical system: scoped access, audit trails, defined data boundaries, reviewed outputs.
Everyone wants a chatbot. Most companies don't need one. Some need a back-office agent workflow. Some need a reporting copilot. Some need document extraction, or exception flagging, or nothing at all yet — they need data hygiene first. The work is figuring out what's actually going to move the business, then picking the smallest thing that does it. Not buying capability and hoping it finds a use case.
Webb Group specializes in helping businesses scale through strategic acquisition, and in shepherding founder-led companies to a well-run exit. I sit on that team and advise across every phase of the deal.
The team is exceptional — a rare mix of deal experience, operating instinct, and creativity. Being part of it is a privilege, and it's what makes my other work land harder: when a client is ready to scale by acquisition or step off at the right moment, we have a real bench behind it.
webbgroup.co ↗When a client has a strong platform and wants to scale faster than organic allows — we build the thesis, run the search, and execute the deals.
For owner-operators ready to convert years of work into a real outcome. Strategic or PE — positioning, process, and protection of the founder's upside.
Fifteen years running and growing my own companies, plus an MBA and years of interim executive management. I bring the operating instinct, the financial read, and the negotiations necessary to every transaction the team touches.
Twenty years of operating is what lets me sit across from a founder or a buyer and actually understand the stakes. That's what I try to bring to every deal the team touches.
I live outside Franklin, TN with my family. On weekends I'm usually on a trail somewhere in a Land Cruiser that's been built for abuse — heavily modified, heavily customized, and proud of every scar.
Off-camber lines, stuck recoveries, broken parts, and a merry band of idiots who think a broken axle is a story, not a problem. Best reset I've got.