Secondary · AI Strategy Advisory
Strategic-level AI advisory. Without the full install.
Quarterly minimum commitment. Continues quarter-to-quarter after.
CEOs, COOs, Chiefs of Staff, board-level operators who want an AI advisor at the strategy layer. Most useful for companies 50-500 employees.
Monthly executive briefings. Quarterly strategic reviews. On-call response when something material happens in the AI landscape. For companies that want a senior advisor at the strategy level — without committing to a full Company Install.
When advisory is the right shape.
Some companies aren’t ready for a full Company Installbut need senior AI thinking at the strategy table. They’re making decisions about AI investments, vendor relationships, organizational structure, and strategic positioning where the cost of getting it wrong is high but operational deployment isn’t yet the right move.
The AI Strategy Advisory exists for that shape. A retainer at the leadership level — not operational support, not implementation, not “ask me technical questions.” A senior advisor who’s on your side, has context on your company, and is on call when material strategic moves come up.
Pairs well with companies that have an internal AI lead doing the operational work. The internal person handles deployment, the advisor handles strategy. The advisor doesn’t need to know every operational detail; the internal lead doesn’t need to make every strategic call alone.
What the retainer covers
Five touchpoints.
Monthly executive briefing
90 min with the executive sponsor (CEO, COO, Chief of Staff). What's happening in the AI landscape, what's coming on the strategic agenda, what decisions need to get made in the next 30–60 days.
Quarterly strategic review
3 hours with the broader exec group. Where the AI landscape is heading over 12–18 months. What investments compound. What to avoid. Most clients say this alone is worth the retainer.
On-call response
When something material happens (vendor announcement, competitor move, internal decision needing AI input), I respond within one business day with a written read.
Vendor / tooling reviews
When you're evaluating an AI vendor relationship, I review the proposal and give you the honest read — including calls vendors won't make themselves.
Board prep
When AI is on the board agenda, we work together on the materials. Half the advisor's value is making the executive sponsor look sharp when they're presenting.
“The advisor's value is partly in making the executive sponsor look sharp when they're presenting to the board.”
Quarterly minimum, then quarter-to-quarter
Start with the Diagnostic Call.
The first quarter is the ramp. Past that, the retainer continues quarter-to-quarter with 30-day notice to end. Most clients stay past year one because the macro trend keeps moving.
Pricing — $2,500 vs $5,000.
The $2,500/mo tier covers monthly briefing + quarterly review + on-call response. Right shape for companies 50–200 employees where the AI footprint is real but not yet institutionally complex.
The $5,000/mo tier adds depth: a second monthly briefing (different exec, typically head of operations or CIO), sub-day on-call response, and quarterly board prep. Right shape for 200–500 employees or for companies in active strategic motion (M&A, restructuring, new market entry).
Above 500 employees or for highly strategic engagements, the right shape is usually the Enterprise tier of the Company Install, which includes the strategic advisory layer alongside operational deployment.
What this isn’t: operational support (that’s the Company Install or Workflow Sprint), technical advisory (that’s the Brain Lifeline), or vendor-affiliated. I don’t take referral fees from AI vendors. The advisory works because I’m structurally on your side.
Common questions
Asked, answered.
How is this different from a fractional CTO?
A fractional CTO typically owns the technical operations of the company. The Strategy Advisor doesn’t — they sit at the strategy table and inform decisions. The advisor is more like a board observer or strategic advisor than an operational leader. Many companies have both: a fractional CTO handling the technical operations and a Strategy Advisor handling the AI-strategy question specifically.
Can multiple executives use the retainer?
At $2,500 the retainer is anchored to one executive sponsor — typically the CEO or COO. At $5,000, two executives can be primary points of contact. Beyond that, the right structure is an Enterprise Install with the strategic advisory layer built in.
What happens during a quarter where nothing material happens in the AI landscape?
The monthly briefings still produce value because the AI landscape doesn’t respect quarter boundaries — something material happens roughly every 3-6 weeks at this pace. In the rare full quarter where nothing major lands externally, the quarterly review focuses on internal strategic positioning: how is the company’s AI thesis holding up, what should the next quarter focus on, what investments are paying off vs. underperforming.
Is there a minimum commitment?
One quarter (three months). The advisory works because of accumulated context — the first month is mostly ramp. After the first quarter, the retainer continues quarter-to-quarter with 30-day notice to end.
Can I scope a single strategic review without the ongoing retainer?
Yes — that’s a one-off engagement, typically $7,500-$15,000 for a 4-6 week strategic project ending in a deliverable. Sometimes the strategic review turns into the advisory retainer; sometimes it’s a standalone. The Diagnostic Call is where we scope which shape fits.
Adjacent paths
Where this connects.
Start with the Diagnostic Call.
The Diagnostic Call commits to nothing. If this install isn’t the right shape for your work, I’ll tell you what is.
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