Lessons from David Singleton

David Singleton is the former CTO of Stripe and a previous VP of Engineering at Google.

On Hiring and Team Building

Hiring is the most important thing you do. Your early team will define the company's trajectory more than any other single decision. [1]
Look for force multipliers, not just high-performers. "You want to find people who raise the bar, not just meet it. Hiring people who can teach you something every day — that's the goal." [1]
Hire for intellectual honesty and fast learning. At Stripe, the focus was on hiring people who were intellectually honest, quick to learn, and willing to take ownership of problems. [1]
Avoid over-titling in the early days. In a startup's early stages, you need builders, not just managers. A senior title doesn't guarantee the right fit for a small, hands-on team. [1]
Look for versatile builders. Early on, prioritize hiring people who can adapt and grow with the company, rather than those who are used to a more structured, large-company environment. [1]
Hire product-minded engineers. Stripe famously waited a long time before hiring its first product managers, which fostered a culture of product-minded engineers who were deeply connected to user problems. [2]
Hiring at scale without Leetcode. Stripe moved away from traditional whiteboard interviews because they aren't a great simulation of an engineer's actual work. They focused on more practical, real-world problem-solving in their hiring process. [3]
Talent is available in unexpected places. The pandemic showed that some of the most talented people can become available for hire. Singleton encourages looking to industries like hospitality for well-trained leaders and employees. [4]
Your team should be guided by the user. Attract talent by having a clear mission that matters. People are motivated by the idea of helping users at scale and want to be guided by the problems those users face. [2]
Surround yourself with people who will do your work. As a leader, your goal is to build incredible teams with people you are developing for the future, who can eventually take on the work you are doing. [5]

On Leadership and Management

Happy teams aren't always the highest performing. "Teams that are perfectly happy are rarely performing at their very best potential." [3]
Making a team happy is not the same as getting the best impact. As an early manager, Singleton learned that just focusing on team happiness doesn't always lead to the best outcomes or the most memorable career moments for the team members. [3]
The transition to managing managers is a big gap. The skills required to manage a single team are very different from those needed to manage other managers. It requires a shift in perspective from direct intervention to coaching and guiding. [3]
The difference between a VP and a Senior EM is about ambiguity. A VP at a company like Google deals with a much higher level of ambiguity and is responsible for setting the direction for a larger part of the organization. [3]
All engineering leaders should write code. Singleton believes that leaders who code stay connected to the realities of their team's work and the challenges they face. [3]
Clarity is a superpower. The best founders and leaders can crisply and compellingly articulate what their company does and why it needs to exist now. [1]
Scale yourself through effective communication. As a manager, you need to find ways to communicate well to scale your impact across the organization. [3]
A leader's job is to build great brands and incredible teams. Singleton sees his role as inspiring and leading people, not just managing tasks. [5]
Be a coach leader. Singleton was advised to become a coach because he had been a "coach leader" his whole life, combining his skills and international knowledge to work with people. [5]
Recognize and lean into periods of crisis. Periods of emotional movement, psychological change, and challenges to mental health are opportunities to discover a lot about yourself and your work if you dig into the "why." [5]

On Product Development and Strategy

Iterate fast and get feedback from the right users. Stripe's "Extreme Product Design" involves creating a minimum viable product, getting it in front of users, and documenting their feedback before continuing to build. [6]
Start small, stay flexible, and adapt fast. This is the secret to building products that users will love. Even the best technology can fail if you don't listen to your users. [6]
Users have more needs than we can ever think of. "Users have more needs than we could ever think of, so we have to find ways to understand them and get their feedback." [6]
Be meticulous in your craft. One of Stripe's core principles is to be meticulous in the details of what you are building. [6]
The process is a loop: ideate → build → ship → feedback. Adding the feedback layer and treating the process as a continuous loop is what leads to products that consistently meet user expectations. [6]
Relentless passion to solve user problems delivers great results. A great example is how a Stripe team worked with the IRS to drastically speed up the process for businesses to get an Employer Identification Number, simply by repeatedly asking, "Does it have to be this way?". [2]
Friction logging improves products. Stripe uses a process called "friction logging," where employees document any difficulties they encounter while using their own products, which helps to identify and fix issues. [2][7]
Build economic infrastructure for the internet. This is how Stripe views its mission—not just as a payments company, but as a builder of fundamental infrastructure for online businesses. [2][8]
Find the confluence of user need and adjacency. Stripe decides what to build next by looking for problems that are adjacent to what they already solve and where there is a strong user need for a solution. [2]
Execution over time is what matters. "It's all about execution over time. With the right focus, we can build things that touch millions of people's lives and help make them successful." [6]

On Career Growth and Personal Development

Find fulfillment by figuring out what you want from your work. Instead of just chasing the next level or promotion, understand what truly gives you energy, whether it's the flow state of coding, having a big impact, or working with a great team. [3]
Great founders are learning machines. The founders who are most admired are not the ones with all the answers, but the ones who learn the fastest. [1]
The world doesn't owe creative people a living. This is a hard truth, but understanding it is key to navigating the complex intersection of art and commerce. [9]
There are more ways out there now than ever before. For creative people and entrepreneurs, the playing field is more level than it has ever been, even if it's just as tough to succeed. [9]
Don't be afraid to change your path. After building the DGM record label to a certain size, Singleton realized he was no longer doing what he set out to do and made the decision to scale it back to what was important to him. [9]
Be what you want to be, not what others expect. Singleton's decision to become a "transformational growth coach" came from a desire to define his own path rather than fitting into a pre-defined box. [5]
Be "conventionally unconventional." This means finding ways to do things differently and break the rules within a larger structure to achieve your goals. [5]
Your international experience broadens your perspective. Working with different cultures and nationalities teaches you valuable lessons, such as how to be a better listener. [5]
Don't wait for others to reach out. If you want to connect with someone, take the initiative. As Singleton reflected on a past work relationship, "we've got my number... why should it be me" who always has to initiate? [5]
Pick up your startup dreams. After a successful corporate career, Singleton decided to leave Stripe to start his own company, returning to a dream he had before joining the company. [10]

On Company Culture

Set the culture from the early days. The foundation you set with your first few hires and decisions will have a lasting impact on the company's culture. [1]
A strong mission attracts the right people. People join Stripe because they believe in the mission of helping businesses at scale. This shared motivation is a cornerstone of the culture. [2]
A culture of curiosity is core to success. At Stripe, the culture of curiosity and continuous improvement was a key factor in their success. [1]
Become a learning community. As a company scales, it's crucial to be deliberate about maintaining a user-first approach and transforming the organization into a learning community. [6]
The power of collaboration is essential. Especially in challenging times, brilliant brands, people, and minds are ready to work together. Collaboration can lead to a stronger emergence from difficult periods. [4]
Users first. This is a core operating principle at Stripe, guiding decisions and priorities across the company. [6]
Move with urgency and focus. Another of Stripe's operating principles that drives the pace and direction of their work. [6]
Seek feedback. A cultural norm of actively seeking feedback is essential for continuous improvement. [6]
Deliver outstanding results. This principle sets a high bar for the quality and impact of the work done at the company. [6]
An ethical business model is possible. Discipline Global Mobile (DGM), the record label Singleton co-founded with Robert Fripp, was explicitly set up as "a model of ethical business in an industry founded on exploitation." [11]

Learn more:

Lessons from David Singleton

On Hiring and Team Building

On Leadership and Management

On Product Development and Strategy

On Career Growth and Personal Development

On Company Culture

Written by Antoine Buteau

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