Today’s episode

There are hundreds of guides on writing PRDs with Claude. Dozens on running user interviews. Almost nothing on how a VP of product actually uses it.

Matt Wensing is VP of Product and Design at Customer.io. They crossed $100M ARR, just shipped an AI agent, and are one of the fastest growing companies in B2B SaaS right now. I asked him to show me his actual documents, his actual Slack threads, and the exact sessions where Claude helped him produce leadership grade output.

What he showed me changed how I think about AI for leaders. Claude has the instincts of a brilliant new hire, it wants to deliver before it fully understands what you need, and at the VP level that gap shows up fast. Matt has spent months figuring out how to manage it, and in this episode he shows you everything.

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Key Takeaways:

1. Take inventory before you open Claude - Before building anything, list every piece of raw material you already have. Zoom recordings, strategy docs, past presentations. The quality of what you feed Claude determines the quality of what comes out.2. Pivot content, do not write from scratch - Claude's best use case is transformation, not creation. Give it two inputs and ask it to reorganize one into the shape of the other. Matt calls this matrix multiplication.3. Build slides first - Build the visual story first. Screenshot the finished slides and feed them back into the same Claude session. Ask it to write a talk track that adds depth using all the context it already has, not one that just repeats the slide.4. Kill eager suggestions immediately - The moment Claude asks if you want it to generate the next thing, say stop. You control the pace. A 200-iteration session with a great deliverable beats saying yes to the first draft every time.5. Start sessions in the abstract - If you reveal the domain too early, Claude pattern matches to the nearest template. Keep it abstract. Build a clean mental model first. Reveal the domain only when the framework holds up on its own.6. Layer complexity in slowly - Start with the simplest version of the framework. Let Claude stabilize on the basics before you add exceptions. Dumping everything in at once produces a lost in the woods experience for both of you.7. AI alignment decks always backfire - When you one-shot an alignment deck, you flatten the problem. Senior executives have spent months living with the real complexity. They feel the thinness immediately, even when they cannot say why.8. Decompose the problem before building anything - Challenge yourself to explode a nasty problem into all its pieces before you touch Claude. Put those observations into the context window first. Then assemble the solution.9. The Slack scanner keeps leaders close to the ground - Customer.io built an AI scanner that monitors dozens of Slack channels and surfaces threads where a product person should be involved. It runs continuously without overwhelming. 10. Chiefys audits your strategy docs automatically - Chiefys is a Slack bot that holds Customer.io's ratified company documents and checks new work against all of them. It flags contradictions and stale documents so nothing goes invisible after you ship something new.

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Related content

Podcasts

PM’s Guide to Claude - YouTube | Spotify | Apple

How to Become a Builder PM - YouTube | Spotify | Apple

We Built an AI Product Manager in 58 mins - YouTube | Spotify | Apple

Newsletters

How to Use Claude for Work

How to Build Product Strategy with Claude Code

The PM OS

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Where to find Matthew Wensing: