Executive AI Cohort
This does the opposite of a chat-window course. It puts working tooling in the executive’s own hands, in their environment, on their systems, against their data, and then trains the judgment to run it.
- Format
- Cohort of six to eight, drawn from different companies
- Sessions
- Eight group sessions across six months
- Cadence
- Every two weeks for months one and two, then monthly
- Between sessions
- Scheduled one-on-ones, then open office hours
- Who it is for
- CEOs and C-suite of lower-middle-market companies
The same program also runs in-house: delivered inside one company, for that company alone, with a group of champions drawn from its own staff. If you are moving a team rather than one or two executives, that is the version you want. In-Company Acceleration.
What success looks like
Six months in, a participant knows what the technology can do, what their own systems will permit, where their organization’s constraints sit, and where the edge of their personal capacity is. They can name what they need help with, scope it, and judge whether it was done well.
Independence from all outside help was never the goal. No CEO builds their own ERP integration, and none should. The goal is that they stop guessing. Most executives buying AI work today cannot tell a good proposal from a bad one, which is why so much of that spend is wasted. This produces the rarest thing in the market: a buyer who knows what they are buying.
Why the room is mixed
Every cohort draws from multiple companies, and that decision drives most of what follows. The highest-value thing in the room is cross-company: a distributor’s inventory problem hands the services firm an idea it would never have generated internally. That only happens across company lines.
Candor is also higher, not lower. Executives are more honest with peers who do not sit in their org chart and do not compete with them. A single-company room has politics in it; a mixed one does not.
We screen for direct competitors and keep them out of the same cohort, and each session works one participant’s real problem live, in front of the group, with their consent.
Why this audience specifically
At this scale the person in the room can grant the access. No committee, no three approvals, no six-week wait for a system connection. That one fact changes what is possible in a six-month program.
They also have nobody to delegate this to. There is no head of AI, no innovation team, no analytics group. If the CEO does not build the capability, nobody does, which makes personal capability the only viable path.
The shape of the program
- 01
Discovery and access
Months 1–2 · every two weeks- Environment and workflow: everyone leaves session one with tools running and one real task from their own job done live
- The resource inventory: what you can reach, who holds the credentials, and what is simply unreachable
- Getting connected: real permissions, real company data, and honest workarounds for what will not connect
- Judgment, guardrails, and data posture: where these tools fail, what to verify, and what leaves your walls
- 02
From operator to program leader
Months 3–6 · monthly- From tasks to systems: work that runs on a schedule without you
- Building for the team: handing a workflow to two other people, and where adoption stalls
- Leading the program: finding real use cases, disqualifying bad ones, and measuring it in terms a board or sponsor will accept
- Capstone: what each participant built, what it produces, what it cost, and what they still need help with
- A working environment they own and can rebuild
- A documented inventory of what their company’s data landscape permits
- At least one workflow running on its own and producing real output
- Verification habits and a clear-eyed view of the failure modes
- A 90-day organizational plan, pressure-tested by peers
- A specific list of what they need outside help with, and the vocabulary to specify and evaluate it
- A small peer network of CEOs at the same altitude with the same problem
- A paid AI seat with desktop app access
- Authority over their own systems, or a direct line to whoever holds it
- Real work to bring. An executive with no current operational problem gets nothing from this
- Roughly two hours a week between sessions, which is the most underestimated item on this list
An executive who can identify, scope, and lead AI work inside their own organization without us in the room.
Where this sits
- Three months
In-Company Acceleration
Your champions, your systems, your work. One company moving fast.
- Project-scoped
Do-It-With-You Consulting
We help you get a project done, building alongside your people instead of in place of them.
Not sure which one you need? The assessment scopes it, and names who from your company should go into it.
Want to talk through this one?
A conversation about where you are, what you are trying to change, and whether this is the right place to start.