The Claude Workflow Nobody at the VP Level Is Showing You

Matt Wensing is VP of Product and Design at Customer.io, a company that crossed $100M ARR. In this episode, he pulls back the curtain completely. Real documents, Slack threads and Claude sessions. He built a full company all hands presentation in one morning, runs metrics retrospectives with his peer C-suite using Claude as a thinking partner, and has built an always on AI layer inside Slack that keeps him close to the ground while he is deep in 200-iteration sessions. Full Writeup: https://www.news.aakashg.com/p/how-to-use-claude-vp-guide Transcript: https://www.aakashg.com/how-a-vp-of-product-uses-claude-without-producing-slop/ Customer.io: http://customer.io/productgrowth -- Timestamps: 00:00 - Intro 01:57 - Why most AI content misses the leadership tier 03:15 - Matt introduces what viewers will learn today 04:06 - The all-hands presentation story begins 06:19 - Take inventory before you open Claude 07:27 - How to use Zoom transcripts as raw material 9:44 - Ads 12:14 - Matrix multiplication, pivoting content into strategic shape 13:50 - Build slides first, then talk track 15:08 - The eager junior problem and how Claude races ahead 19:02 - The biology metaphor session begins 23:21 - The game night rule for layering complexity 26:08 - Revealing the domain only when the model is clean 36:26 - How to decompose problems before building anything 38:17 - Why AI alignment decks backfire on executives 40:56 - Matt's full weekly AI stack 45:06 - Chiefys and how Customer.io audits strategy docs -- Thanks to our sponsors: LogRocket - Find the bugs killing your conversion before your users do - https://logrocket.com/ I ran a head-to-head eval to see if that's true, verify here - https://www.news.aakashg.com/p/logrocket-review 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. -- Where to find Matt Wensing: LinkedIn: https://www.linkedin.com/in/wensing/ X: https://x.com/mattwensing 1:1 Video Consultation: https://intro.co/MattWensing Where to find Aakash: X/Twitter: https://x.com/aakashgupta LinkedIn: https://www.linkedin.com/in/aagupta/ Newsletter: https://www.news.aakashg.com #productmanagement #claude #aitools -- About Product Growth: The world's largest podcast focused solely on product + growth, with over 200K+ listeners. Subscribe and turn on notifications.

Matt WensingguestAakash Guptahost

Jun 5, 202650mWatch on YouTube ↗

EPISODE INFO

Released: June 5, 2026
Duration: 50m
Channel: Aakash Gupta
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

Matt Wensing is VP of Product and Design at Customer.io, a company that crossed $100M ARR. In this episode, he pulls back the curtain completely. Real documents, Slack threads and Claude sessions. He built a full company all hands presentation in one morning, runs metrics retrospectives with his peer C-suite using Claude as a thinking partner, and has built an always on AI layer inside Slack that keeps him close to the ground while he is deep in 200-iteration sessions. Full Writeup: https://www.news.aakashg.com/p/how-to-use-claude-vp-guide Transcript: https://www.aakashg.com/how-a-vp-of-product-uses-claude-without-producing-slop/ Customer.io: http://customer.io/productgrowth -- Timestamps: 00:00 - Intro 01:57 - Why most AI content misses the leadership tier 03:15 - Matt introduces what viewers will learn today 04:06 - The all-hands presentation story begins 06:19 - Take inventory before you open Claude 07:27 - How to use Zoom transcripts as raw material 9:44 - Ads 12:14 - Matrix multiplication, pivoting content into strategic shape 13:50 - Build slides first, then talk track 15:08 - The eager junior problem and how Claude races ahead 19:02 - The biology metaphor session begins 23:21 - The game night rule for layering complexity 26:08 - Revealing the domain only when the model is clean 36:26 - How to decompose problems before building anything 38:17 - Why AI alignment decks backfire on executives 40:56 - Matt's full weekly AI stack 45:06 - Chiefys and how Customer.io audits strategy docs -- Thanks to our sponsors: LogRocket - Find the bugs killing your conversion before your users do - https://logrocket.com/ I ran a head-to-head eval to see if that's true, verify here - https://www.news.aakashg.com/p/logrocket-review 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.
1. 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.
1. 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.
1. 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.
1. 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.
1. 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.
1. 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.
1. 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.
1. 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.
1. 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. -- Where to find Matt Wensing: LinkedIn: https://www.linkedin.com/in/wensing/ X: https://x.com/mattwensing 1:1 Video Consultation: https://intro.co/MattWensing Where to find Aakash: X/Twitter: https://x.com/aakashgupta LinkedIn: https://www.linkedin.com/in/aagupta/ Newsletter: https://www.news.aakashg.com #productmanagement #claude #aitools -- About Product Growth: The world's largest podcast focused solely on product + growth, with over 200K+ listeners. Subscribe and turn on notifications.

SPEAKERS

Matt Wensing
guest
VP of Product and Design at Customer.io, sharing executive-level Claude/LLM workflows and internal AI enablement practices.
Aakash Gupta
host
Host and creator focused on AI workflows for product leaders, interviewing guests and sharing tools and resources via aakashg.com.

EPISODE SUMMARY

In this episode of Aakash Gupta, featuring Matt Wensing and Aakash Gupta, The Claude Workflow Nobody at the VP Level Is Showing You explores a VP-level Claude workflow for strategic decks, not PRDs The core leadership skill for effective AI use is rigorous problem decomposition, because LLMs will flatten complexity and generate “slop” if the problem isn’t broken into crisp parts.

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