AI Roadmap Engagement

Three differences. First, depth — the Strategy Session is a single 90-minute call producing an 8–12 page roadmap; the Engagement is 4–6 weeks of work producing a 30–50 page roadmap. Second, stakeholder scope — the Session is for solo founders making solo decisions; the Engagement interviews 3–6 stakeholders and builds team alignment. Third, output rigor — the Session is fast strategic input; the Engagement includes technical audits, vendor selection frameworks, and 12-month execution plans designed for teams to execute against. The Strategy Session fee can credit toward the Engagement.

The Engagement is a finite project (4–6 weeks) producing a finite deliverable (the roadmap). The Retainer is ongoing (monthly) with weekly working sessions and execution oversight. Many clients run the Engagement first to produce the roadmap, then transition to the Retainer to execute against it. The Engagement fee can credit 50% toward the first month of a subsequent Retainer if that path makes sense.

At minimum: the founder/CEO making the AI investment decisions. Ideal: 3–6 stakeholders covering revenue (CMO, head of growth), technical (CTO, lead engineer), and operations (COO, ops lead). Each stakeholder is interviewed for ~45 minutes once during weeks 2–3. The leadership team attends 2 group sessions: mid-engagement review (week 3) and final delivery (weeks 5–6).

Starting from $2,500 for smaller teams (2–3 stakeholders, single-channel ecommerce). Typical engagements run $3,500–$4,500 for mid-size brands (3–5 stakeholders, multi-channel or multi-brand). Complex engagements run $5,000 for $20M+ businesses, large stakeholder groups, or multi-region/multi-brand portfolios. Quoted as fixed price after the discovery call.

Executive summary, current state assessment (with specific waste identified), business model to AI opportunity mapping, prioritized opportunity matrix (6–12 opportunities with ROI estimates and execution risk), vendor selection framework, 12-month execution plan with quarterly milestones, change management plan addressing team capability gaps, and appendices with detailed analysis from stakeholder interviews and the technical audit.

Three common paths. Path 1 (most common): the leadership team executes the roadmap internally with 60 days of email Q&A access for clarifying questions. Path 2: the engagement transitions to a Fractional AI Lead Retainer for ongoing execution oversight (50% of engagement fee credits toward first retainer month). Path 3: I am retained for specific high-leverage implementations identified in the roadmap (Pinterest engine, AI schema, SaaS replacement, etc.). All three paths are valid depending on team capacity.

The Engagement is right for businesses making meaningful AI investments — typically $100K+ in annual AI/SaaS spend, or considering committing $100K+ to AI in the next 12 months. Below that scale, the simpler Strategy Session ($500) typically delivers better ROI because there are fewer stakeholders, less existing waste to identify, and less complexity to map. I will tell you honestly during the discovery call which engagement type fits your stage.

Book a free 30-minute scoping call through the contact page. Come with: your annual revenue, your annual AI/SaaS spend, the number of stakeholders who would need to participate, and the most urgent AI decision currently on your plate. I will scope the right engagement size and confirm fit honestly. Most engagements start within 14 days of the scoping call.