Building a culture of excellence | David Singleton (CTO of Stripe)

Stripe is a name synonymous with excellence in the tech world, not just for its powerful financial infrastructure but for the incredible talent it attracts and cultivates. How does a company build such a resilient and innovative culture? It’s a question that perplexes leaders everywhere. From holding off on hiring product managers for years to embedding its CTO directly into engineering teams, Stripe’s approach is unconventional yet profoundly effective. It's a system built on a deep, almost obsessive, focus on the user and an unwavering commitment to craftsmanship.

In a detailed conversation, Stripe's Chief Technology Officer, David Singleton, pulls back the curtain on the operating principles that guide one of the world's most valuable private companies. He reveals the tactical processes behind their values, from "friction logging" to "engineer-cations," and explains how these practices empower a massive engineering organization to move with both speed and precision. This is a look inside the engine room of a company that is not just building products, but defining a new standard for excellence.

Key Takeaways

• Mission-Driven Hiring: Stripe's success in attracting top-tier talent stems from its core mission—increasing the GDP of the internet. This clear, compelling purpose attracts product-minded builders who are patient, collaborative, and driven by long-term impact.
• Operationalizing Craftsmanship: The principle "be meticulous in your craft" is not just a slogan. It's brought to life through concrete practices like friction logging, where team members meticulously document user journeys to find and fix pain points, leading to significant product improvements.
• Co-Creating with Users: Stripe's product development is rooted in a deep partnership with a select group of early users. By building in tandem with companies like Figma and Slack for its Billing product, Stripe ensures its solutions are battle-tested and perfectly aligned with real-world needs before a wider launch.
• Balancing Speed and Reliability: Stripe achieves a rare feat: deploying code over 16 times a day while maintaining 99.999% uptime. This is made possible by a heavy investment in automated testing, gradual rollouts, and a culture that prioritizes learning from every incident.
• Leaders Stay in the Trenches: Through unique practices like "engineer-cations," senior leaders, including the CTO, regularly embed themselves within teams to write code. This provides invaluable, firsthand context on the developer experience and keeps leadership grounded in the realities of building the product.

The Stripe Flywheel: How Mission Drives Talent Acquisition

Many companies claim to have a "high bar" for hiring, but Stripe’s ability to attract and retain industry-defining talent goes much deeper. It starts with a thesis that resonates with a specific type of builder: the belief that the internet economy has immense, untapped potential. This mission—to increase the GDP of the internet—serves as a powerful filter, drawing in individuals who are motivated by building foundational infrastructure for other businesses to thrive.

Beyond the High Bar: A Mission That Matters

Stripe’s origin story is rooted in solving a difficult, unglamorous problem: making online payments simple for developers. This focus on building infrastructure that works quietly behind the scenes attracts long-term thinkers who find satisfaction in tackling complex challenges. It's a culture that values tenacity and collaboration over splashy launches. As David Singleton explains, this singularity of purpose is the foundation upon which the entire team is built. People join Stripe because they want to participate in a mission that matters, guiding their work through deep, personal relationships with the users they serve.

The Art of Patient and Personal Hiring

Unlike companies that treat recruiting as a high-volume machine, Stripe approaches it as a deeply personal and patient activity. Hiring managers are intimately involved, partnering closely with the recruiting team to identify needs and build genuine relationships with candidates. This often means waiting for the right person, even if they aren't immediately available. By investing time to understand a candidate's personal and professional aspirations, Stripe can frame the opportunity not just as a job, but as the most significant learning and growth experience they could undertake. This personal touch ensures that new hires are not just filling a role but are deeply aligned with the company's mission and culture from day one.

Building Products the Stripe Way: Co-Creation and Craftsmanship

Stripe famously operated for years, growing to around 200 employees, before hiring its first dedicated product manager. This was possible because the company cultivated an engineering team that was inherently product-minded. Every engineer was expected to understand user problems deeply, a trait that remains a cornerstone of Stripe’s product development philosophy today.

From Product-Minded Engineers to a PM-Led Powerhouse

The early Stripe team consisted of engineers who also acted as product managers. For a developer-focused API, this model was incredibly effective. The engineers building the product were its target users, allowing for an intuitive grasp of customer needs. Today, with a broader suite of products serving everyone from startups to Fortune 500 companies, dedicated product managers play a critical role. They act as the "locomotion" that brings together cross-functional teams—including engineering, design, financial partnerships, legal, and risk—to build cohesive products. PMs are responsible for synthesizing user feedback, defining product strategy, and ensuring all the moving parts align to serve a long-term vision.

The Co-Creation Playbook: Building with Your First Users

Stripe’s approach to product development revolves around identifying the right set of early users and co-creating a solution with them. This methodology ensures the product solves real, pressing problems before it's released to a broader audience.

We decided to co-create the product with them.

A prime example is Stripe Billing. The team identified existing users like Figma and Slack who were pushing the limits of Stripe's payments API for their subscription models. By establishing shared Slack channels and conducting regular product demos, the Stripe team created a tight feedback loop. Only when this initial alpha group was "super, super happy" did Stripe consider the product ready for a wider release. This process means every engineer exercises the attributes of a product manager, ensuring user needs are woven into the fabric of the product from the very beginning.

Operationalizing Excellence: "Be Meticulous in Your Craft"

"Be meticulous in your craft" is one of Stripe’s core operating principles. While many companies aspire to such a standard, Stripe has built systematic processes to make it a daily reality. This isn’t about achieving perfection at the expense of speed; it's about being intentional about where to apply an obsessive level of detail to create a superior user experience.

What is Friction Logging?

One of the key tools for achieving this is friction logging. This practice requires a team member—often a PM or engineering manager—to put themselves in a specific user’s shoes and walk through an entire product flow from start to finish. They take meticulous, stream-of-consciousness notes, highlighting every point of confusion, delay, or frustration. For years, David Singleton has personally onboarded as a new Stripe user every month, writing a friction log and sharing it with the relevant teams. This systematic process of stepping back and viewing the product holistically helps maintain a cohesive experience, even as thousands of engineers work in parallel.

From Small Details to a 10.5% Revenue Uplift

The impact of this meticulousness is tangible. By sweating the details in its hosted checkout flows—removing a click here, reducing latency there—Stripe has been able to deliver significant value. A recent analysis found that users who migrated from a basic integration to Stripe's optimized checkout surfaces saw an average revenue increase of 10.5%. In an industry where improvements are often measured in hundredths of a percentage point, this compounding effect of small, deliberate changes demonstrates the immense business value of true craftsmanship.

Walk the Store: Aligning the Company on User Experience

To scale this mindset across the entire organization, Stripe occasionally conducts a practice called "walk the store" during its all-hands meetings. The company collectively walks through a critical product flow, discussing how it reflects company priorities and the user experience. This shared ritual creates a common language for discussing product quality and reinforces the importance of user-centricity for every employee, regardless of their role. It’s a powerful way to ensure that the bar for craft is understood and upheld by everyone.

Engineering at Scale: Speed, Reliability, and Staying Connected

Stripe operates in a high-stakes environment. As the financial backbone for millions of businesses, its systems must be incredibly reliable. At the same time, the company needs to innovate rapidly to meet evolving user needs. Holding these two seemingly contradictory goals—stability and velocity—in tension requires a sophisticated engineering culture and a powerful set of internal tools.

The Paradox: Deploying 16 Times a Day with 99.999% Uptime

Stripe’s core API sees an average of 16.4 deployments per day. This rapid cadence is enabled by a robust, automated system. Every code change is run through a massive battery of automated tests before it can even be considered for production. Once merged, changes are automatically deployed to a small percentage of traffic and gradually ramped up, allowing for early detection of any issues. Critically, Stripe fosters a learning organization where every incident is meticulously reviewed. The goal isn't just to fix the immediate problem but to prevent an entire class of similar issues from happening in the future. These remediations are prioritized above new feature work, reinforcing the non-negotiable importance of reliability.

What is an "Engineer-cation"?

To ensure leaders don't become disconnected from the day-to-day realities of their teams, Stripe encourages a practice called an "engineer-cation." For three or four days, a manager or executive clears their schedule, joins a team, and picks up a small coding task. The goal is to experience the entire development process firsthand—from the tools and build infrastructure to the code review process and documentation. This immersive experience provides invaluable context that informs better decision-making and helps leaders empathize with the challenges their teams face.

The Crying Octopus: A Simple Tool for Big Productivity Gains

One of the simplest yet most effective tools for improving developer productivity at Stripe is a small button embedded in every internal tool: an emoji of a crying octopus. When an engineer encounters friction—a slow process, a confusing error, a piece of broken documentation—they can click the octopus and type a brief description of the problem. This "paper cut" feedback is collected and reviewed by the developer productivity team, providing a frictionless channel for identifying and prioritizing small improvements that have a compounding impact on the entire engineering organization.

The Future is Now: How AI is Reshaping Stripe

While the recent buzz around AI is new, Stripe has been using machine learning at the core of its products for years, particularly for fraud detection with its Radar product. Now, the company is actively integrating large language models (LLMs) to enhance both its external products and internal operations, seeing a massive opportunity to better serve its users.

Empowering Users with AI: From Docs to SQL Queries

Stripe is leveraging AI to make its powerful tools more accessible. One of the first applications was an AI-powered assistant for its extensive documentation. By training GPT-4 on its docs, Stripe allows developers to ask natural language questions and get immediate, synthesized answers. Another powerful application is within Sigma, its custom analytics product. Users can now describe the business question they have in plain English—like "which country has the fastest growing sales?"—and the system will automatically generate the corresponding SQL query. This unlocks deep business insights for non-technical users and demonstrates AI's potential to democratize access to complex data.

Fostering Internal AI Adoption

Internally, Stripe has embraced tools like GitHub Copilot to accelerate development, finding that it helps engineers focus on high-level architectural problems rather than boilerplate code. To make LLMs safely accessible for internal use cases, Stripe built its own UI on top of models like GPT-4. A key innovation was creating a library of shareable prompts, or "presets." This allows a team member in marketing to perfect a prompt for generating blog posts in Stripe's tone, which can then be used by anyone in the company. This collaborative approach is accelerating the adoption of AI and unlocking new efficiencies across all functions.

Conclusion

Stripe's success is not accidental; it is the result of a deeply intentional culture built on a few core pillars. It begins with a powerful mission that acts as a magnet for the right kind of talent. It is sustained by operationalizing abstract values like "craftsmanship" into concrete, daily practices that everyone can follow. And it scales through a relentless focus on creating tight feedback loops—with users, with internal tools, and between leaders and their teams. By combining a long-term vision with a meticulous, user-first approach to execution, Stripe has created a durable model for building a culture of excellence that any organization can learn from.