00About
Senior advisor. AI builder. SME C-suite altitude. One person, end to end.
The role most $5M–$50M companies need right now is structurally unfilled. Big firms won’t come down. AI explainers don’t ship. Builders work at hyperscale, not at your altitude. I work the intersection.
- Subject
- Stuart Leo
- Role
- Operator
- Based
- Australia
Twenty years working with SME leaders. The pattern is the same.
The business is ten or twenty years old. The founder built it and it works. The technology stack aged. The operating model aged. The leadership team didn’t scale. And every conversation now has the same line item: AI.
The reset isn’t one project. It’s four threads at once: strategy, leadership, operations, and the software the operating model now needs. Big firms won’t come below fifty million. Boutiques specialise too narrowly. Independents are usually one-trick.
I wrote the framework. Built the platform that operationalises it. For the exclusive few — I run the engagements myself, hands on the keyboard alongside the leadership team.
Three things in one operator.
Most operators are good at one of the three. The rarer ones at two. All three in one operator is the work I run — and the moat underneath it.
- 01
Senior advisory altitude
Two decades across executive seats, advisory work, and founder seats. Comfortable in the room with the CEO, the board, and the operating team — and not interchangeable with someone three rungs down.
- 02
Hands on the keyboard
The AI doesn't get outsourced to a delivery team. I write the strategy, build the tooling, and ship the agents that run inside the operating model. The thinking and the doing happen in the same head.
- 03
SME C-suite engagement zone
$5M to $50M revenue, 10–20 years old, founder- or family-owned. The altitude where the full reset matters and where one operator can hold all four threads at once. Not hyperscale. Not a startup. Where the work actually lives.
One is common. Two is rare. All three in one operator is the moat. Senior advisory altitude. Hands on the keyboard. SME C-suite engagement zone. That is the seat the engagements run from.
Most of the work doesn’t live on the public web.
The biggest impact happens inside companies. Internal tools. Agents. Automations. Transformation programs that aren’t mine to publicise. The brands come out in conversation.
The /work page is the sanitised version — what the work looks like with the names removed. The frameworks are in the books. Live thinking is in the briefings. Everything else is the engagement.
Where the proof lives.
- R.01See the work
The work
Sanitised case studies across strategy, leadership, ops, and software.
- R.02Read the book
The book
Resolute. In print since December 2024. The frameworks the website uses and Waymaker operationalises — in one place.
- R.03Listen to the briefings
The podcast
Commander in Brief. Weekly fifteen-minute briefing — a real leadership decision in the news, connected to the framework.
- R.04Visit Waymaker
Waymaker
The platform that operationalises the framework. Founded and built by the same operator who runs the engagements.
How the engagement actually runs.
A multi-year, fixed-rate engagement with one operator sounds like a heavy commitment. It isn’t, and the structure is why. Hiring me is materially lower-friction than hiring an exec, retaining a firm, or bringing in a coach.
Diagnostic
4–8 weeks · paid · time-boxed
Joint scope of the four threads. Written recommendation at the end. Either side can walk after this — the off-ramp is structural, not awkward.
Embedded
12–36 months · fixed rate · 30-day notice both ways
Sitting with the leadership team, hands on the keyboard. Continuous delivery, not project milestones. No SOWs, no change orders, no junior team.
Handover
Engagement ends because the org doesn’t need it anymore
The systems, the leadership team, and the operating model stay. The engagement ends because the work is done — not because the calendar said so.
Why this is structurally lower-risk than the alternatives.
vs. an executive hire
30-day notice both ways. No severance choreography. No HR cycle. No PIP. Easier to release than the average employee.
vs. a consulting firm
No SOWs. No change orders. No junior delivery team doing the actual work. One operator. One number. One throat to choke.
vs. a coach or fractional
Hands on the keyboard, not just on the whiteboard. No title, no ego — tell me the problem, I'll work out how to fix it.
The reset window is real work. Twelve to thirty-six months of it. The window is open now. Three years from now, the businesses that didn’t start are the ones being acquired by the ones that did. There is no 90-day version of this.