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Lenny's Podcast: Product | Growth | Career
Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead)

Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead)


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Jeff Weinstein is a product lead at Stripe, where he helped grow their payment APIs to hundreds of billions in volume and transformed the way founders start companies into a few simple clicks with Atlas. Prior to Stripe, Jeff led several startups and sold companies to Groupon and Box. He’s known for his customer obsession, craft, quality, and building beloved products businesses rely on. In our conversation, we discuss:

  • The power of customer obsession and how to operationalize it in the product development process

  • How to pick the right metrics and use them to drive impact

  • Techniques for getting things done at big companies

  • A group practice Jeff started to uplevel product craft, called Study Group

  • The story behind Stripe Atlas and its mission to increase entrepreneurship globally

  • Lessons from working with the founders of Stripe

Listen now on Apple, Spotify, and YouTube.

Some takeaways:

  1. Before focusing on craft, experience, or quality, you need to ensure that you’re solving a burning problem for someone. One of Jeff’s first companies went offline for hours and not a single customer reached out—that’s when he knew they didn’t have product-market fit. If users aren’t clamoring for your product, you’re not solving a real need. Think about it this way: solving the core problem is the main course; perfecting craft, UX, and quality are the desserts.

  2. Jeff emphasizes the “go, go, go ASAP + optimistic, long-term compounding” approach: seize opportunities with enthusiasm while maintaining a strategic focus on long-term growth. Stripe’s evolution in global payment methods exemplifies how combining rapid execution with thoughtful, enduring strategies leads to significant, sustainable results.

  3. When customers take the time to complain or provide feedback, treat it as a gift. Respond promptly to complaints or feedback, even if it means interrupting other tasks, as it creates a direct signal between you and the customer. This responsive attitude can lead to a loyal customer base and product improvement.

  4. Ask customers to describe what a “bad day” looks like when using your product, and then find ways to track metrics around those frustrations. You don’t necessarily need to solve every issue right away, but having this problem library builds awareness to inform your roadmap.

  5. Customer obsession is critical for building great products. Jeff recommends several techniques for staying close to customers:

    1. Practice silence: Use silence effectively to encourage potential customers to share their true needs. Allow them the space to express themselves without rushing to fill the gaps in conversation.

    2. Communicate directly: Reach out directly via platforms like X or through personal contact methods like texting to gather feedback and resolve issues quickly.

    3. Respond quickly: Act swiftly when customers raise concerns or issues. Addressing problems promptly can prevent escalations and turn detractors into promoters.

    4. Humanize interactions: Treat each customer as an individual with unique needs and concerns, rather than just a number or statistic. Build genuine connections and partnerships.

6. Stripe uses “study groups” to get participants in the mindset of customers, thereby gaining fresh insights into product usability and customer experience. Anyone in the company can show up for study groups, and they are asked to completely detach from their roles at the company and immerse themselves in the persona of a customer of a fictional company (e.g. Dolphin Aquarium Industries). They adopt the goals and challenges of this fictional customer to simulate real-world scenarios. The primary goal of study groups is to build empathy and understanding, not to solve problems or critique the product.

Where to find Jeff Weinstein:

• X: https://x.com/jeff_weinstein

• LinkedIn: https://www.linkedin.com/in/jeffwweinstein/

• Email: jweinstein@gmail.com

In this episode, we cover:

(00:00) Jeff’s background 

(10:16)  The “go, go, go ASAP + optimistic, long-term compounding” approach

(15:38) The importance of craft and quality

(24:15) Effective customer communication strategies

(28:57) The importance of speed in customer interactions 

(33:19) Narrowing your focus

(36:53) Why you should pay attention only to paying-customer feedback

(40:24) Practicing silence when communicating 

(45:33) The role of metrics in product success

(54:08) Empowering teams with a single metric

(58:23) Picking the right metric for your audience

(01:05:10) The importance of metric hygiene

(01:11:33) How Stripe uses “study groups” for product improvement

(01:37:20) Stripe’s Atlas: simplifying company formation

(01:50:38) Automation and operational efficiency

(01:55:13) Diversity and team building

(02:03:09) Building new products within a large company

(02:21:10) Lightning round


• Atlas: https://stripe.com/atlas

• Stripe: https://stripe.com/

• SQL: https://en.wikipedia.org/wiki/SQL

• GitHub: https://github.com/

• Linear: https://linear.app/

• Figma: https://www.figma.com/

• Jeff’s tweet about Stripe’s bug-finder program: https://x.com/jeff_weinstein/status/1777487507934040300

• The “Collison installation”: https://news.ycombinator.com/item?id=18400504

• How we use friction logs to improve products at Stripe: https://dev.to/stripe/how-we-use-friction-logs-to-improve-products-at-stripe-i6p

• Fidelity: https://www.fidelity.com/

• 83(b) election: https://docs.stripe.com/atlas/83b-election

• Jeff’s tweet about Atlas’s NPS score: https://x.com/jeff_weinstein/status/1788644576330469638

• What is a Delaware corporation? Here’s what makes this state so attractive to businesses: https://stripe.com/resources/more/what-is-a-delaware-corporation

• Incorporating in Delaware explained: Why it’s such a popular option for businesses: https://stripe.com/resources/more/incorporating-in-delaware-explained

• 7 of Pixar’s Best Storyboard Examples and the Stories Behind Them: https://boords.com/blog/7-of-pixars-best-storyboard-examples-and-the-stories-behind-them

• Alex Kehayias on LinkedIn: https://www.linkedin.com/in/alexkehayias/

• Patrick McKenzie on LinkedIn: https://www.linkedin.com/in/patrickmckenzie/

• AngelList: https://www.angellist.com/

• Dan Hightower on LinkedIn: https://www.linkedin.com/in/danhighto/

• Stripe Atlas perks partners: https://support.stripe.com/questions/stripe-atlas-perks-partners

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884

Orbiting the Giant Hairball: A Corporate Fool’s Guide to Surviving with Grace: https://www.amazon.com/Orbiting-Giant-Hairball-Corporate-Surviving/dp/0670879835

7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

• Box: https://www.box.com/

• Patrick Collison on X: https://x.com/patrickc

How to with John Wilson on HBO: https://www.hbo.com/how-to-with-john-wilson

The Quiet Girl on Hulu: https://www.hulu.com/movie/the-quiet-girl-b50a4b8e-d3ff-4635-b806-5e7dbd292ca4

• Raycast: https://www.raycast.com/

• Quicksilver: https://qsapp.com/

• Alfred: https://www.alfredapp.com/help/workflows/automations/

• CleanShot: https://cleanshot.com/

• John Collison on X: https://x.com/collision

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

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Lenny's Newsletter
Lenny's Podcast: Product | Growth | Career
Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.