How is this different from a fractional CTO?

A fractional CTO owns the company’s technical operations. The Strategy Advisor doesn’t — they sit at the strategy table and inform decisions, more like a board observer than an operational leader. Many companies have both: a fractional CTO handling 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 — the AI landscape doesn’t respect quarter boundaries, and something material happens roughly every 3-6 weeks at this pace. In the rare quarter where nothing major lands externally, the review turns inward: how is the company’s AI thesis holding up, what should next quarter focus on, what investments are paying off vs. underperforming.

Is there a minimum commitment?

One quarter (three months). The advisory works on accumulated context, and the first month is mostly ramp. After that, it continues quarter-to-quarter with 30-day notice to end.

Can I scope a single strategic review without the ongoing retainer?

Yes — a one-off engagement, typically $7,500-$15,000 for a 4-6 week strategic project ending in a deliverable. Sometimes it turns into the advisory retainer; sometimes it’s standalone. The Diagnostic Call scopes which shape fits.

Secondary · AI Strategy Advisory

Strategic-level AI advisory. Without the full install.

Price$2,500 – $5,000 / monthBook →

Duration

Quarterly minimum commitment. Continues quarter-to-quarter after.

Who it fits

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. For companies that want a senior advisor at the strategy level — without the full Company Install.

How it works

Diagnose. Build. Hand you the keys.

One method, three moves: we map your actual work, build your private brain from it, and hand you the keys — owned, portable, queryable from anywhere.

We map your actual work — the tools, the gaps, the shape your role needs.

We build your private brain from it — your corpus, indexed and queryable.

It's yours. Reach it from any LLM, at your own subdomain. You own it.

How the advisory works.

A senior advisor at the strategy table — on a cadence, on call, on your side.

A 90-minute briefing with the executive sponsor. What’s moving, what’s coming onto the agenda, what decisions need making in the next 30 to 60 days.
A vendor announcement, a competitor move, an internal decision needing AI input — a written read within a business day. Vendor and tooling reviews get the honest call.
A three-hour strategic review on where the landscape heads over 12 to 18 months — what compounds, what to avoid, and board prep when AI is on the agenda.

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 deciding on AI investments, vendor relationships, organizational structure, positioning — where getting it wrong is costly but operational deployment isn’t yet the move.

The AI Strategy Advisory is for that shape. A retainer at the leadership level — not operational support, not implementation, not “ask us technical questions.” A senior advisor on your side, with context on your company, on call when material strategic moves come up.

Pairs well with an internal AI lead doing the operational work. The internal person handles deployment, the advisor handles strategy. The advisor doesn’t need every operational detail; the internal lead doesn’t make every strategic call alone.

“The advisor's value is partly in making the executive sponsor look sharp when they're presenting to the board.”

What the retainer covers

Five touchpoints.

Monthly executive briefing
90 min with the executive sponsor (CEO, COO, Chief of Staff). What's happening, what's coming on the agenda, what decisions need making in the next 30–60 days.
Quarterly strategic review
3 hours with the broader exec group. Where the landscape heads over 12–18 months. What compounds. 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 — a written read within one business day.
Vendor / tooling reviews
When you're evaluating an AI vendor, we review the proposal and give the honest read — including calls vendors won't make themselves.
Board prep
When AI is on the board agenda, we work the materials together. Half the advisor's value is making the executive sponsor look sharp when they present.

Quarterly minimum, then quarter-to-quarter

Start with the Diagnostic Call.

The first quarter is the ramp. Past that, it continues quarter-to-quarter with 30-day notice to end. Most clients stay past year one because the macro trend keeps moving.

Book the Diagnostic Call→Or read Enterprise (advisory included)↗

Pricing — $2,500 vs $5,000.

$2,500/mo covers monthly briefing + quarterly review + on-call response. Right shape for 50–200 employees where the AI footprint is real but not yet institutionally complex.

$5,000/mo 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 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. We take no referral fees from AI vendors. The advisory works because we’re structurally on your side.

Common questions

Asked, answered.

How is this different from a fractional CTO?
A fractional CTO owns the company’s technical operations. The Strategy Advisor doesn’t — they sit at the strategy table and inform decisions, more like a board observer than an operational leader. Many companies have both: a fractional CTO handling 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 — the AI landscape doesn’t respect quarter boundaries, and something material happens roughly every 3-6 weeks at this pace. In the rare quarter where nothing major lands externally, the review turns inward: how is the company’s AI thesis holding up, what should next quarter focus on, what investments are paying off vs. underperforming.
Is there a minimum commitment?
One quarter (three months). The advisory works on accumulated context, and the first month is mostly ramp. After that, it continues quarter-to-quarter with 30-day notice to end.
Can I scope a single strategic review without the ongoing retainer?
Yes — a one-off engagement, typically $7,500-$15,000 for a 4-6 week strategic project ending in a deliverable. Sometimes it turns into the advisory retainer; sometimes it’s standalone. The Diagnostic Call scopes which shape fits.