AI Product Diagnostic — AI Shepard
4-week diagnostic · Fixed fee

Before you build more AI,
find out what's actually going wrong.

The AI Product Diagnostic is a focused, four-week engagement that diagnoses what's going sideways — in the product and in how the team is building it — and ends with a specific, opinionated plan for what to fix first.

Book a free intro call
Who it's for

Built for B2B product teams mid-build — when something is already going sideways.

If your team has shipped AI features that aren't landing, has AI on the roadmap without a clear strategy, or is using AI tools without changing how decisions get made — this diagnostic was designed for you.

B2B SaaS & Tech Professional Services Platforms 20–100 employees AI features in market or on roadmap No dedicated AI product strategist

AI shipped but adoption is low — the team knows something is off but can't diagnose whether it's a product problem, a positioning problem, or both

AI is on the roadmap but nobody owns the strategy — tools are being chosen before the customer problem has been defined

The team uses AI tools but decisions haven't changed — roadmaps still run on gut feel, discovery still takes the same amount of time

Build vs. buy vs. partner is unresolved — evaluating vendors without a clear view of what problem you're solving or what good looks like

Sales is hiding the AI features in demos — reps can't articulate the value prop and prospects aren't converting because of it

What you receive

Every deliverable is immediately usable — not filed away after the readout.

The diagnostic ends with a complete package your product, sales, and CS teams can act on the same week.

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Executive Summary

Two-page summary of diagnostic findings and strategic rationale — built for board and investor communication.

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Customer Pain-to-AI Opportunity Map

Real customer friction points mapped to realistic AI interventions, evaluated for business impact and technical feasibility.

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AI Feature Audit with Gap Analysis

What's been built, what's working, what isn't, and where the gap between product intent and customer reality lives.

⚖️

Build vs. Buy vs. Partner Evaluation

For each prioritized opportunity — the right approach, relevant vendors or APIs, and the tradeoffs the team needs to own before committing.

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GTM-Ready AI Narrative

How to talk about your AI to customers, prospects, and the market — grounded in the problems it actually solves, not the features it contains.

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Retainer Proposal

A specific engagement structure built around the decisions that surfaced in the diagnostic — not a generic advisory menu.

What comes next

The diagnostic is the entry point. The retainer is where the work continues.

Most AI product initiatives stall not because the strategy was wrong, but because no one with the right experience stays in the room through the hard parts — the vendor decisions, the spec tradeoffs, the launch stumbles. The diagnostic ends with a specific proposal for staying on as your ongoing AI Product Partner.

Three tiers, scoped to how deep the work goes: Advisory, Embedded, and Operational.

See the AI Product Partner retainer →

Diagnostic clients receive preferred scheduling and onboarding within one week of diagnostic completion.

If this sounds familiar, that's worth a conversation.

A free 20-minute intro call. No pitch, no pressure — just a direct conversation about what's going sideways and whether there's a fit.

Book a free intro call