Retainer
Ongoing AI strategy and product leadership — without the $400K+ full-time hire.
Senior leadership, built into your operating rhythm.
Your company needs a strategic counterweight. Someone who's been in the room before — across industries and decades — who can push back on bad ideas, sharpen good ones, and help the team make better decisions every month as AI reshapes your competitive landscape.
A Retainer is fractional Chief AI and Product Officer-level thinking on a regular cadence. AI strategy, product direction, vendor evaluation, competitive positioning, and team development — from someone who doesn't just advise on these things but has actually done them. For travel and hospitality companies specifically, you get an advisor who has owned and built businesses in the industry, not just consulted for it.
You need CPO-level thinking but can't justify a $300K+ hire
Your company isn't big enough — or early enough — for a full-time Chief Product Officer or Chief AI Officer. But the strategic decisions being made right now will shape the next three years. A Retainer fills that gap at a fraction of the cost, without the recruiting timeline or equity dilution.
Strategic decisions keep getting made by committee
No product voice in the room means decisions default to the loudest opinion, the most recent board suggestion, or whatever the last vendor pitched. A Retainer provides the experienced counterweight that keeps the team focused on what actually matters.
AI is reshaping your category and nobody on your team is tracking it
AI-native competitors are entering your market. Vendors are pitching solutions every week. Your board is asking questions the team can't answer with confidence. A Retainer means someone is always evaluating the landscape and advising on what to act on — and what to ignore.
You've done a project or assessment and want to keep the momentum
Many Retainer relationships start after a Project or Assessment. The diagnostic is done, the strategy is set — now you need someone embedded in the operating rhythm to make sure it actually gets executed and adapted as conditions change.
Strategy sessions
Two 60–90 minute sessions per month. Structured, focused conversations about AI opportunities, product direction, competitive moves, and strategic decisions. Not status updates — working sessions that move things forward.
Async access
Reach out via Slack or email between sessions. 24-hour response on business days. When something can't wait for the next scheduled session — a vendor eval, a board question, a competitive move — you're covered.
Quarterly review
Every 90 days: step back and assess what worked, what shifted, and how AI is changing the landscape around you. Delivered as a written summary with recalibrated priorities for the next quarter. Not just a call — a document you can share with the board.
Ongoing advisory scope
AI strategy and roadmap, product direction and prioritization, vendor evaluation and build/buy/partner decisions, competitive positioning, UX and experience design input, team development and organizational design.
Month 1 — Immersion
Deep dive into your product, technology stack, competitive landscape, team structure, and AI readiness. This includes reviewing existing documentation, a stakeholder listening tour, and establishing the session rhythm. The goal: build enough context to start adding value immediately.
Month 2 — Traction
Strategy sessions shift from diagnostic to directive. Specific recommendations on product direction, AI priorities, and competitive positioning. By now the context is deep enough for the advice to be sharp — not generic.
Month 3 — First quarterly review
Formal assessment of what's working, what's changed, and what the next quarter should focus on. Written summary delivered. This is also the natural decision point: most clients see enough value by month three to continue. If it's not working, that conversation happens honestly.
What this is
Strategic guidance across AI strategy, product direction, UX architecture, competitive positioning, vendor evaluation, and team development. The kind of thinking that shapes the decisions that matter most.
What this isn't
Writing PRDs, managing sprints, or attending daily standups. A Retainer is designed for leaders who want a trusted strategic partner, not another resource to manage. If hands-on execution is needed, that's scoped as a separate Project. And I'm not on-call for emergencies — the cadence is structured and predictable, which is how the thinking stays sharp.
Compounding value
The longer the relationship, the deeper the context and the sharper the advice. Month one is good. Month six is significantly better. Cross-pollination from working across multiple companies and industries simultaneously means the pattern recognition is something even a great full-time hire can't match.
What you get each quarter
Session notes and action items from each call. A written quarterly review with strategic assessment and recalibrated priorities. Async guidance and input between sessions. And an advisor who's tracking AI developments as they relate to your specific business — not as general news.
Your time commitment
Two 60–90 minute sessions per month, plus occasional async exchanges. Plan for roughly 3–4 hours per month of direct engagement. The quarterly review adds about 2 hours once every 90 days.
Who should participate
The CEO, CPO, or senior leader who owns the product and AI decisions. Sessions work best with 1–2 consistent participants. Other team members can join specific sessions as topics warrant.
Timeline
Minimum 3-month commitment. Most clients continue for 6–18 months as strategic needs evolve. The relationship is most valuable when it's embedded in the operating rhythm — not treated as a periodic check-in.
Investment
Starting at $8,000/month based on company size and complexity. A full-time Chief AI or CPO costs $250K–$400K+ fully loaded. A Retainer delivers the same caliber of strategic input at a fraction of the cost — without the recruiting timeline, equity dilution, or long-term commitment of a senior hire.
"J's guidance is perfect for anyone who has to create and deliver a competitive, distinct experience. The playbook for a toolset tried and trusted by today's wildly successful brands."
"Few have logged as many hours as J, thinking deeply about product design and the methodologies that lead to success. This book captures years of wisdom."
"J clears up so much about the process of building products and makes it easy for designers, developers, and business people to understand and apply."