💡

InsightHunt

Hunt the Insights

K

Kevin Yien

Episode #173

Head of Product, Merchant Experiences

Stripe

⚡Execution🎯Product Strategy👥Team & Culture🔍User Research

📝Full Transcript

17,130 words
Kevin Yien (00:00:00): The PM job can become a little too internal, influencing my stakeholders and getting alignment and all these things. But if you can't sell or support your own product, I don't trust you to build the product. Lenny Rachitsky (00:00:10): You think every PM should keep a decision log? Kevin Yien (00:00:13): We all talk about product sense. To me, it's just a fancy way of saying you can make good decisions with insufficient data. PMs need as many reps as possible in making decisions, documenting the rationale behind those decisions, and then crucially seeing the outcome of them. Lenny Rachitsky (00:00:28): We have a lot of interesting approaches to hiring, including this idea of a unsell email. Kevin Yien (00:00:31): When you get to offer stage, I send an email and I say all the terrible things that are probably going to reinforce their fears. If you can tell them that upfront and they can read that whole email and still be equally excited to join you, find yourself a A+ hire. Lenny Rachitsky (00:00:45): I'm curious if you found any interesting uses of AI in your work. Kevin Yien (00:00:49): We are not even beneath the dust on the surface when it comes to what's going to change. Lenny Rachitsky (00:01:00): Today, my guest is Kevin Yien. Kevin leads product for merchant experiences at Stripe. Before that, he built the restaurant business and the ecosystem teams at Square, and most recently was head of product and design at Mutiny. He also makes ice cream and, as you'll hear in there conversation, was a pretty competitive eater for some part of his life. (00:01:17): In our conversation, Kevin shares a ton of unique and insightful perspectives on how to be a successful product manager, including how to get into product management, how to improve your relationship with your engineers and designers, bunch of advice on hiring, why you should keep a decision log, how to automate your customer research, plus a ton of really powerful stories around...

💡 Key Takeaways

  • 1PMs should start as engineers, designers, or salespeople to understand the 'potential energy' of a team before managing it.
  • 2Writing is clarity at scale; if you can't sell or support your product through writing, you shouldn't build it.
  • 3Use 'Decision Logs' to build product sense by documenting rationale and reviewing outcomes later.
  • 4Send an 'Unsell Email' at the offer stage to be radically transparent about the job's downsides.
  • 5Automate user research by triggering workflows from sales call transcripts (Gong) to schedule interviews.
  • 6PMs define the constraints (perimeter), allowing engineers and designers to be creative within the box.

📚Methodologies (4)

⚡ Execution

The PM's role is to draw the perimeter of the problem space by applying strict constraints (target user, platforms, trade-offs). Once the box is defined, engineers and designers have full autonomy to fill that box creatively with the best solution.

Core Principles

  • 1.Define strict constraints (e.g., target user segment, availability, speed vs. consistency).
  • 2.Let the team 'fill the box' with creative solutions within those constraints.
  • 3.Obsess over the final deliverable quality, even down to interaction details.

"PMs should be doing everything in their power to draw the perimeter of the problem space. And it's within that, eng, design... can go as crazy as they want."

#perimeter#execution#process
View Deep Dive →
The Decision Log

by Kevin Yien

🎯 Product Strategy

Product sense is the ability to make good decisions with insufficient data. To improve this, PMs must log their decisions (or predictions of others' decisions), document the rationale, and review them after a set period to validate their intuition.

Core Principles

  • 1.Identify a decision point (internal or external market event).
  • 2.Write down the decision and the specific rationale (the 'why').
  • 3.Set a calendar reminder (e.g., 6 months) to review the outcome against the rationale.

"PMs need as many reps as possible in making decisions, documenting the rationale behind those decisions, and then crucially seeing the outcome of them."

#decision#strategy#product
View Deep Dive →
The Unsell Email

by Kevin Yien

👥 Team & Culture

At the offer stage, send a candid email listing the 'terrible' things about the role and company (e.g., poor work-life balance, chaos). If the candidate is still excited, they are a high-retention A+ hire.

Core Principles

  • 1.Wait until the offer stage (you need to know their specific fears first).
  • 2.List ~8 bullet points of genuine downsides or harsh realities.
  • 3.Be available to discuss these points immediately if the candidate hesitates.

"If you can tell them that upfront and they can read that whole email and still be equally excited to join you, find yourself a A+ hire."

#unsell#email#team
View Deep Dive →
🔍 User Research

Treat your sales and support teams as a research engine. Use automation tools to listen for triggers in customer conversations and automatically invite those customers to research sessions without manual intervention.

Core Principles

  • 1.Identify keywords relevant to your product (e.g., competitor names, feature issues).
  • 2.Set up alerts (e.g., Gong to Slack) when these keywords are mentioned in calls.
  • 3.Automate outreach (e.g., Zapier to Email) to send a Calendly link immediately.

"There is a world of difference between reading a report about a line cook and then standing with a line cook."

#automated#research#users
View Deep Dive →
← Browse All Episodes