Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny)
August 18, 2024
AI Summary
5 min readKevin Yien, who leads product for merchant experiences at Stripe, shares unorthodox tactics for product management drawn from his time at Square and Mutiny. He frames PM work as converting a team's potential energy—engineers, designers—into realized customer value with minimal loss, emphasizing direct customer exposure, clear constraints, and deliberate reps for better decisions.
Building foundations for PM success
Yien advises against jumping straight into product management; instead, start in roles like engineering, design, or sales to gain frontline exposure to building and customer problems. These build a unique perspective that PMs leverage to coordinate teams effectively, avoiding the trap of being "okay at everything but world-class at nothing." Great PMs must also write compellingly—not just crisp PRDs, but messaging that sells the product in the customer's voice—because writing creates clarity at scale and forces thought crystallization, as Joan Didion noted. Improve by consuming compelling writing (Paul Graham essays, not just PM docs) that pushes action, varying sentence cadence to hold attention.
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What you'll learn
- 1 *(00:03:29) **Entering Product Management: Start in Foundational Roles**
- 2 *(00:12:47) **PMs Must Be Great Writers for Clarity and Sales**
- 3 *(00:19:10) **PM-Eng-Design Dynamics: Draw Perimeter, Obsess on Details**
- 4 *(00:35:13) **Decision Log: Build Product Sense Through Reps**
- 5 *(00:46:50) **Hiring Tactics: Unsell Email for A+ Fits**
- 6 *(00:54:01) **Automate User Research for Direct Customer Exposure**
- 7 *(01:02:26) **AI Insights and Failure Lessons**
+ Full timestamped outline available in the app
Show Notes
Kevin Yien leads product for merchant experiences at Stripe. Before that, he meandered his way from being a technical designer to a product manager, built the restaurants business and ecosystem team at Square, and most recently was head of product and design at Mutiny. He also makes ice cream and teaches for fun. In our conversation, we discuss:
• Why aspiring PMs should start in engineering, design, or sales
• The importance of writing skills, and how to become a better writer
• How to automate user research
• Kevin’s “unsell email” technique for hiring
• The value of keeping a decision log
• Insights on AI and its impact on future generations
• Lessons from failure
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Find the transcript and show notes at: https://www.lennysnewsletter.com/p/unorthodox-pm-wisdom-kevin-yien
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Where to find Kevin Yien:
• LinkedIn: https://www.linkedin.com/in/kevinyien/
• Website: https://kevinyien.com/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Kevin’s background
(02:00) The story behind Kevin’s profile picture
(08:41) The role of a product manager
(10:48) Getting started in product management
(12:47) The importance of writing skills
(15:06) Becoming a better writer
(19:10) The PM’s role with engineering and design
(28:41) Drawing the perimeter for your team
(31:37) Feedback tips
(35:13) Decision logs and product sense
(45:36) Unorthodox hiring strategies
(47:01) The unsell email strategy
(54:01) Automating user research
(01:02:27) AI in everyday life
(01:06:05) Lessons from failure
(01:14:34) Lightning round
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