Jeff Weinstein, a prominent product lead at Stripe, is recognized for his profound insights on product development, customer-centric strategies, and fostering a culture of excellence. Through various interviews and public discussions, he has shared a wealth of knowledge for product managers, entrepreneurs, and anyone passionate about building meaningful products.

On Product Philosophy and Strategy

  1. "Go, go, go ASAP + optimistic, long-term compounding." This is Weinstein's core philosophy, advocating for immediate, energetic action on opportunities while maintaining a strategic, long-term perspective for sustainable growth. [1][2]
  2. "Craft is kind of a dessert that you get after the meal of does your thing solve a real problem in the world." He emphasizes that while quality and craftsmanship are important, they are secondary to solving a genuine and pressing customer problem. [1]
  3. "The worst failure is to try to make something great that no one cares about." This highlights the critical importance of validating a problem's significance before investing heavily in building a polished solution. [2]
  4. "You want to pick something that's juicy enough to work on for a really long time." Weinstein advises choosing problems that are substantial and meaningful, providing long-term motivation and impact. [3]
  5. "When I look back on those errors, they weren't errors of execution. They were errors of strategy and picking the wrong problem." He reflects on past failures, attributing them to poor problem selection rather than a lack of effort or skill in execution. [3]
  6. "Product management is simple. It's not easy. But it's simple." This quote encapsulates the idea that the core principles of product management are straightforward, even if their application is challenging. [4]
  7. "If you want your project or company to last a while, it's going to have to be self-sustaining at some point." Weinstein underscores the importance of building a viable business model where customers are willing to pay for the value provided. [2]
  8. "You have to find stuff that people really want to the point where the likelihood of having to send out the 'hey, I'm sorry we build cool stuff, it's no longer running' is low." This is a stark reminder of the ultimate goal: creating products that are indispensable to their users. [2]
  9. "Some of the things we want to accomplish... can't be solved in the afternoon. They're going to require layers of infrastructure, and services and applications, and UI, and Partnerships." This speaks to the necessity of a long-term, layered approach for complex and ambitious projects. [1]
  10. "I'm now completely obsessed with finding a problem that... if you solve it, you will be happy you completely solved it." This reflects his passion for tackling significant challenges that lead to fulfilling outcomes. [3]

On Customer Obsession and Feedback

  1. "When customers take the time to complain or provide feedback, treat it as a gift." He views customer feedback, even negative, as an invaluable opportunity for improvement and connection. [2]
  2. "The fact that someone took their finite time to... communicate to the world or you about your product that's an unbelievable gift." This further emphasizes his deep appreciation for any form of user engagement. [1]
  3. "I will leave a meeting. I will change what I'm doing to just get one message back to them." This demonstrates his commitment to rapid response and showing customers they are heard. [4]
  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." This is a practical technique for identifying and measuring key pain points. [2]
  5. "You don't need 10,000 of those people to talk to. If you're text message friendly with five or 10 of those, you are going to have so much direct signal." He advocates for building deep relationships with a small group of highly relevant customers. [1]
  6. "Practice silence: Use silence effectively to encourage potential customers to share their true needs." This is a powerful communication tactic to allow customers the space to articulate their real problems. [2]
  7. "If you listen with enough silence, they might even say, 'I'll pay you money to solve blah.'" This highlights how patient listening can directly uncover willingness to pay. [1]
  8. "You only pay attention to feedback from people that are paying customers and ignore everything else." Weinstein advises prioritizing feedback from those who have a tangible stake in the product. [1]
  9. "My bar for how we will respond to those folks is not to just sort of solve the problem but is to turn them into a promoter." He sets a high standard for customer service, aiming to transform negative experiences into positive advocacy. [1]
  10. "The best piece of information you'll get from some conversation is the last thing they say." This is an observation on how crucial insights often emerge at the very end of a discussion. [2]
  11. "I'd rather just take it the complete opposite direction which is, 'Tell me what's going on. What's what where does it hurt? Show me your computer.'" His approach to customer conversations is to be open and exploratory rather than leading with a pitch. [2]
  12. "It's not the customer's job to interrupt you and say, 'Hey, could you stop your pitch? I want to tell you about my top problem.'" This is a reminder that the responsibility is on the product builder to listen, not on the customer to guide the conversation. [1]
  13. "One of [my] 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." This is a powerful anecdote illustrating a key signal of a lack of product-market fit. [2]
  14. "You can get a sense of when you're building something if you put it out, is it going to resonate with people... and often it's little things, how quickly they email you back." He points to small, qualitative signals as early indicators of resonance. [3]
  15. "If the meeting is scheduled for 30 minutes... and they want to go 60 minutes to keep going... then you can start [to think] 'oh my goodness.'" Extended engagement from customers is a strong positive signal. [3]

On Execution, Craft, and Quality

  1. "Speed is an important one, which is just reducing the time between the moment the customer felt compelled enough to go out of their way to talk about some problem." He stresses the importance of a rapid feedback loop. [1]
  2. "We will do the work the night before it's due, so let's just make it due tomorrow." This is his "go, go, go" mentality in practice, creating urgency to accelerate progress. [1]
  3. "If you pick some problem that's worth solving and you narrow into the core problem of it, it actually makes it easier to make it high quality." Focusing on the essential problem simplifies the path to a high-quality solution. [3]
  4. "You're no longer having to polish all the corners of all possible things." A narrow focus prevents wasted effort on non-essential features. [3]
  5. "Great people want to work with great people." He believes that talent density is a magnet for more talent, creating a virtuous cycle. [2]
  6. "I try not to use words like 'quality' actually because it feels exclusionary." He prefers to focus on the functional and emotional aspects of a product rather than abstract labels. [2]
  7. "Does it feel like an auteur built it for you?" This is his person-centric definition of a high-quality product experience. [3]
  8. "We need to make things that are deeply functional to the audience and completely solves their problem. And then we want to make things that feel great to use." He outlines a clear hierarchy of needs for product development: function first, then user experience. [3]
  9. "A lot of times people [say] 'I can't believe how quickly Stripe is shipping.' [I feel] like 'Wow, it feels like we're shipping so slowly.'" This illustrates the internal drive for continuous improvement and the feeling of always being behind when you're close to customer needs. [3]
  10. "It's because we're trying to do as much of that work up front so that when stuff goes out to the full internet, it feels like hand-in-glove." He explains that the perception of speed is often the result of meticulous preparation. [3]

On Metrics and Measurement

  1. "To determine the right metrics, I focus on the value we aim to deliver to customers and how we can measure that from their perspective." His approach to metrics is customer-centric, measuring their success, not just internal outputs.
  2. "We focus on a single overarching metric to guide our product development, which helps us prioritize our efforts and make informed decisions." He advocates for the power of a single, unifying metric to align a team.
  3. "How do you know you have product-market fit? Charts that showcase things are going up and to the right on one hand, and tweets on the other." He combines quantitative data with qualitative user feedback to assess product-market fit. [1]
  4. "You should take your app down for a day... you should turn your thing off and see, does the world turn with pitchforks at you? And if it does not... you probably don't have a real thing." This is a drastic but illustrative test for product indispensability. [5]
  5. "Charge them lots and lots and lots of money as another way of sort of making them feel more impassioned for the state of your piece." He suggests that a high price can be a forcing function to reveal a product's true value. [5]

On Career and Personal Growth

  1. "When there's a fork in the road between things you are passionate about and things you are good at, which should you pick?" This is a central question he explores, often leaning towards solving real problems over pure passion projects. [6]
  2. "I didn't realize at the time like that was the signal that I did not... we did not have product-market fit. And I ended up wasting many more years on that project." He shares a personal story of misinterpreting signals and the cost of not pivoting sooner. [1]
  3. "I'm really trying to avoid that situation again." This shows his commitment to learning from past mistakes. [1]
  4. "I had to learn over time to [balance] my instinct of like, let's get it done today... with this longer-term compounding, more strategic mindset." He speaks about his personal development in balancing short-term execution with long-term vision. [1]
  5. "Once you get the feeling of building something and getting it out to another human and seeing them use it, it's so fun, it's so contagious." He describes the intrinsic motivation that comes from creating things for others. [2]
  6. "You just have to remind yourself, 'Oh goodness, like we're supposed to keep working this hard.' It doesn't always get easier the more you do it." A candid reflection on the persistent difficulty of building great things. [2]
  7. "I was building startup stuff at exactly the same moment that the founders of Stripe started Stripe... and that somewhat inspires and haunts me." This is a humbling admission about how timing and problem selection can lead to vastly different outcomes. [2]
  8. "Take an improv class." He recommends improv as a way to get better at active listening and being present in conversations. [1]
  9. "Write down exactly the default dead case of why this thing should not exist." A pre-mortem technique to critically evaluate an idea from a pessimistic perspective. [5]
  10. "Be your own worst enemy." He advises entrepreneurs to rigorously challenge their own assumptions to build more resilient ventures. [5]

Learn more:

  1. Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead) - YouTube
  2. Jeff Weinstein (Stripe) – Conversations on Quality (Episode 03) - YouTube
  3. Jeff Weinstein | Out There - ArtsJournal
  4. Building at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product Lead at Stripe) - Lenny's Newsletter
  5. Product management is simple: Insights from Stripe's Jeff Weinstein - Alex's Newsletter
  6. Jeff Weinstein - The Baffler