Stripe has become a benchmark for product-driven growth, admired for its elegant solutions, customer obsession, and methodical approach to building software. Behind Stripe’s success are product management practices that are unconventional, yet remarkably effective.
These practices transcend traditional frameworks to establish a culture of creativity, precision, and unwavering focus on customer success.
In this blog, we’ll examine seven distinct practices employed by Stripe’s product managers. From leveraging pricing to generate candid feedback to tracking customer frustrations through inventive metrics, these approaches offer profound insights for product teams aiming to craft exceptional products.
Whether you’re seeking to improve decision-making, encourage innovation, or align your team on strategic goals, these practices are both practical and impactful.
7 Insightful Product Management Lessons from Stripe
1. Use Pricing to Drive Honest Feedback
The Practice:
During its beta phase, Stripe priced its product at the higher end of the market. This intentional choice attracted users genuinely invested in the product, rather than those seeking a bargain. By doing this, Stripe ensured they received feedback from customers who truly valued the product and considered it worth the premium price.
As the How They Grow blog explains:
“Feedback is essential at all stages of a company, but particularly when running an MVP around a complex problem. The right feedback can make your business, and the wrong feedback can derail you completely.”
Why It Works:
Pricing acts as a natural filter for feedback. Customers who pay more are likelier to offer sincere, thoughtful feedback because they have a vested interest in the product’s success. This approach also drives product teams to create features that justify the cost, discouraging shortcuts or subpar solutions.
Lesson for PMs:
If you want to validate your product’s value proposition, don’t hesitate to charge for it early on. As Stripe demonstrated, leveraging pricing as a feedback mechanism enables you to concentrate on solving meaningful customer challenges.
2. Simplify the User Experience, Even if It’s Complex Behind the Scenes
The Practice:
In Stripe’s early days, its founders manually processed transactions while presenting a seamless, automated experience to users. They acted as the proverbial Wizard of Oz — managing complexity manually to deliver a straightforward, frictionless experience upfront. This allowed Stripe to refine their product, gather essential feedback, and perfect the user experience before investing in full-scale automation.
This approach is aptly summarized in How They Grow:
“With a WoZ test, you do the work manually in the background while giving the impression of a fully-developed product in the foreground.”
Stripe co-founder Patrick Collison shared how they manually onboarded early customers at Y Combinator:
“When anyone agreed to try Stripe they'd say ‘Right then, give me your laptop’ and set them up on the spot.”
Why It Works:
Building an MVP doesn’t always require immediate automation. By keeping the user-facing experience simple while handling complexity manually, you can test assumptions, optimize workflows, and ensure the product addresses the right problems.
Lesson for PMs:
Don’t let the need for automation or scalability delay your launch. Managing intricate processes manually can be a valid — even strategic — choice during early phases. As How They Grow notes:
“Make something your customers need to do easy, and don’t be too concerned early on with building the whole thing — find the easiest and fastest way to test your idea and go from there.”
3. Conduct “Pre-Mortems” to Identify Risks Before They Become Issues
The Practice:
Stripe’s product managers regularly conduct pre-mortem meetings before major projects or launches. In a pre-mortem, the team imagines that the project has failed six months into the future. They then work backward to identify what might have gone wrong, surfacing potential threats and blind spots. Stripe uses a shared vocabulary during these sessions, categorizing risks as:
- Tigers – Major threats that could kill the project.
- Paper Tigers – Perceived threats that aren't as dangerous as they seem.
- Elephants – Unspoken issues or assumptions that the team might be ignoring.
Shreyas Doshi, a former Stripe PM, explained the power of this exercise:
“The magic of this type of approach... is that it just somehow enables greater psychological safety for team members to talk about things they’re concerned about.”
Why It Works:
Pre-mortems create psychological safety by giving team members permission to voice concerns without fear of being seen as negative. This process helps teams anticipate issues before they arise and take proactive measures to mitigate risks. It also fosters a culture of openness and vigilance that can prevent costly mistakes.
Doshi shared a compelling insight:
“What I noticed as I ran pre-mortems is that in future meetings... people started talking about, ‘Oh, I have this tiger, can I bring up this tiger?’”
This shared vocabulary allows teams to quickly surface concerns in a structured way.
Lesson for PMs:
Regularly hold pre-mortem meetings to uncover risks early. Create an environment where team members can freely express concerns and categorize potential threats using terms like “tigers,” “paper tigers,” and “elephants.” As Doshi summarized:
“A pre-mortem is one of those very low downside, but very high upside things that I’ve experienced.”
4. Use “Decision Logs” to Sharpen Product Sense
The Practice:
Stripe encourages product managers to maintain decision logs. These logs document every product decision made, the rationale behind it, and the expected outcome. This practice helps PMs improve their product sense and provides a historical record that can be referenced to evaluate decisions over time. It also promotes learning from successes and failures.
As Kevin Yien describes in his talk, Unorthodox PM Tips:
“PMs need as many reps as possible in making decisions, documenting the rationale behind those decisions, and then crucially seeing the outcome of them.”
He goes on to explain the benefit of this practice:
“Product sense… is just a fancy way of saying you can make good decisions with insufficient data, and the core of that is decisions.”
Why It Works:
Just as athletes or musicians hone their skills through consistent practice, product managers refine their decision-making abilities by reflecting on past choices. A decision log enables PMs to learn from their experiences and simulate decisions made by others, broadening their perspective over time.
Kevin Yien highlights the power of decision logs with a practical approach:
“You can start super easy by saying, ‘Every Sunday morning I’m going to scroll through Twitter or Hacker News, see something interesting, and make a bet.’ Write it down, set a reminder to check back in a few weeks or months to see what happened.”
Lesson for PMs:
Develop the habit of documenting decisions, even small ones. Reflect on your rationale and revisit decisions later to evaluate outcomes. This simple practice can significantly enhance your decision-making and intuition over time.
5. Encourage Creativity by Embracing Mistakes
The Practice:
Stripe fosters a culture of risk-taking and creativity by promoting the idea of “making some mistakes” during brainstorming sessions. This mindset creates a safe space for teams to propose bold ideas without fear of judgment.
Jeff Weinstein, a product lead at Stripe, shares this mantra:
“I say, ‘Let’s make some mistakes,’ when we’re brainstorming something… to showcase, ‘Let’s be creative. Do whatever you want. No pretense. I’m not evaluating anything.’”
He highlights how this approach eases pressure:
“At that point, everyone’s like, ‘What? Okay, fine. Sure. Cool.’”
Why It Works:
Innovation thrives when teams feel free to propose untested, unconventional ideas. By explicitly encouraging creativity and risk-taking, teams are more likely to explore unique solutions. This approach often uncovers ideas that would otherwise remain unexplored.
Weinstein humorously balances this philosophy with practicality:
“You have to use it in certain circumstances and not for the five nines of reliability on our API, but it does have its place.”
Lesson for PMs:
Create an environment where your team feels safe to brainstorm freely. Encourage them to suggest ideas without fear of failure. Often, the best innovations stem from ideas that initially seem risky or unconventional.
6. Track Metrics That Reflect Customer Pain Points
The Practice:
Stripe places significant emphasis on metrics but goes beyond traditional KPIs to focus on those that truly reflect customer satisfaction and pain points. One standout metric they track is “users having a bad day.” This involves logging events whenever a user encounters a problem, such as hitting a 404 error, experiencing payment delays, or having repeated transaction declines.
As Jeff Weinstein, a product lead at Stripe, explains:
“Users having a bad day... is where we emit a log line anytime we think that a user bumped into a problem. So maybe they hit a 404, or maybe their payout was one day after the ETA, or they had more than 10 payment declines.”
This metric reminds teams to prioritize solving real problems for customers rather than focusing solely on vanity metrics.
Why It Works:
Traditional metrics can sometimes obscure the true state of user experience, while a metric like “users having a bad day” ensures teams remain customer-obsessed. By identifying and addressing the pain points causing user frustration, Stripe stays focused on improving the experiences that matter most.
Lesson for PMs:
Define metrics that are tied to customer satisfaction and pain points. Consider tracking a version of “users having a bad day” within your product to ensure you’re solving meaningful problems. This approach ensures that product development is always aligned with customer success.
7. Visualize Solutions with Sharpie Sketches
The Practice:
When brainstorming solutions, Stripe advocates for starting with “Sharpie sketches” to visually outline the unconstrained perfect solution to a problem. This process prioritizes clarity and simplicity, avoiding the pitfalls of over-complicated digital tools in the initial ideation phase.
Jeff Weinstein describes this approach:
“Storyboarding some solution visually with a Sharpie — not a pencil, not Figma initially, not high or low fidelity.”
By focusing on quick, hand-drawn sketches, teams can visualize the ideal outcome, align on the vision, and then iteratively refine the solution.
Why It Works:
Starting with simple sketches promotes collaboration and creativity by focusing on the essence of the solution. This ensures teams align on the vision before diving into detailed design or implementation.
Lesson for PMs:
When solving complex problems, encourage your team to sketch their ideas with simple tools like a Sharpie. Focus on the “unconstrained perfect solution” and use this visual representation as a foundation for iteration. This can help align stakeholders and ensure everyone shares the same vision before diving into detailed design or implementation.
Wrapping Up
Stripe’s product management practices demonstrate how thoughtful approaches can lead to impactful results. From fostering creativity with “let’s make some mistakes”, brainstorming sessions to using Sharpie sketches to visualize solutions, Stripe exemplifies how combining innovative techniques with a deep focus on customer needs can drive success. Metrics like “users having a bad day” and habits like maintaining decision logs ensure that the team remains grounded in solving real problems while continuously improving their craft.
By adopting these seven practices, product managers and teams can enhance their decision-making, align on customer-first solutions, and foster a culture of innovation and collaboration. In doing so, they’ll be better equipped to build products that not only solve meaningful problems but also delight users in ways that set the standard for excellence.
References:
i. How They Grow - How Stripe Grows
ii. The Art of Product Management | Shreyas Doshi (Stripe, Twitter, Google, Yahoo)
iii. Unorthodox PM Tips: Automating User Insights, Unselling Candidates, Decision Logs, More | Kevin Yien
iv. Building Product at Stripe: Craft, Metrics, and Customer Obsession | Jeff Weinstein (Product Lead)
