Lessons from Michelle Zatlyn, President and COO of Cloudflare

On Entrepreneurship and Getting Started

On the spark of entrepreneurship: "I remember it was Wednesday afternoon i walked out of the three pitches. and I walked into the hallway. and And I said to someone else on the on the on the trip. I said 'Oh my god if that guy can start a company. so could I.' And I meant it...it just kind of demystified. it i was like 'This. person is not special this person has a point of view and cares about something. and they're smart.' Well I'm kind of those things too." [1]
On finding a meaningful problem: "I knew early on before I started to do Cloudflare, that what I really wanted to do is I wanted to work on something I was proud of, that I thought was meaningful." [2]
On the mission: "I love our mission to help build a better internet. Because the internet's becoming more important for every single business. The fact that we're there every step of the way, helping them be a strategic partner? I'm so proud of that." [3]
On starting in a downturn: "If you're one of those entrepreneurs. who are working on your ideas. and thinking man is now the time to start it's definitely possible...it's almost easier to walk away from it because it's like there aren't that many other good things going on so let me go create this thing that I just can't stop thinking about." [4]
On the difficulty of early days: "It is so hard to convince somebody to come work for you when you're just a few people. It's actually easier when you're starting out. I think you're less than 10 people, it's easier to recruit. 10 to 50, someone has to be a little crazy to come work with you." [5]
On the initial vision: When she and her co-founders launched Cloudflare in 2009, they wanted it to become huge. As they put it at the time, it either becomes a monster or it dies. [6]
On early customer acquisition: "First we had this idea and you have to decide, is there actually a company around with this idea? Are you solving a meaningful problem that people care about? I remember early on, it was so hard to get our first 10 customers and even harder to get at our first hundred customers." [7]
On the power of "Just ship it": Weeks before launching at a TechCrunch event, with internal debate about readiness, Zatlyn pushed the team with, "Just ship it." [3]
On finding product-market fit: "That gave me a lot of validation that I had made the right choice, that we were working on the right things. And then over time, I was like, 'OK, we're solving a real, meaningful problem.'" [3]
On the importance of grit over expertise in the early days: In the beginning, determination and resilience were more critical than having all the answers. [8]

On Leadership and Scaling

On evolving as a leader: "Leadership is both an art and a science. As Cloudflare has grown, some parts of Michelle's leadership style has changed while some has stayed the same. She still maintains the detailed understanding of the parts of the business she covers but she executes at a higher level." [9]
On the founder's role in a growing company: "As a founder, you're showing up every single day trying to gain ground against your idea. And it's just so important over the course of the history of the journey of your company to keep showing up for work, to keep staying in the game, staying on the field." [6][10]
On hiring people better than you: "You need to hire a leadership team that's better at you than everything you do...that's how you build an amazing. business right as a team together." [4]
On the transition to manager: "Not only are you a founder, but you're also a manager. And you have to make decisions, and sometimes you're going to make unpopular decisions...you have to see yourself as a manager and a leader, and that was, I think, a hard transition for me early on. But once I got it, I got it." [2]
On handling hiring mistakes: "What I've learned is, don't throw rocks. Do not throw your founders or leaders under the bus. We're in this together. Let's fix it together." [2]
On ruthless prioritization: "Our approach has always, that you have to ruthlessly prioritize. So, the list of things you need to do is always longer than the resources you have available to do them." [11]
On the importance of momentum: "Momentum is your best friend as an early-stage company...The average product development cycle time at a big company is about 16 months. You have to build your product in less time than that." [6]
On scaling intentionally: "It means doing the right things at the right time...when you're scaling it means there's way more to do than time and people to do it. and that is the crux of the issue." [12]
On the power of being founder-led: "I think that a company being founder-led is a superpower...when you're a founder and you own it. it's just different than when you...are a professional operator you just you you obsess over this thing you've created." [12]
On the reality of team turnover: "One of the hardest lessons I've learned as a founder is it's a journey and not everyone is starting and ending the journey at the same time...The faster you realize that...is OK." [6][10]
On the art and science of leadership: Zatlyn emphasizes that leadership is a combination of intuition and learned skills, and founders must embrace being in charge to make effective decisions. [13]
On the difference between hard and impossible: "There's just a huge difference between hard and impossible...humans can do hard things the right group of people can do hard things. but if something's impossible because of physics or technically or there's some reason why it's impossible well that's a different thing let's not spend time on something that's impossible." [14]
On communication as a key skill: "The communication matters so much in your career especially the more senior you get and it is not all equal." [14]
On making decisions with incomplete information: "You're going to find yourself in a situation where you are not anywhere near credible to make a decision, but you have to make a decision...this rate at which you're learning matters a ton." [2]
On being patiently impatient: In the early days, everyone is focused on speed. As the company grows, processes are introduced which may slow things down, but ultimately improve the quality of the output. [9]

On Company Culture and Team Building

On the democratic nature of culture: "The only truly thing that's democratic in a company is is the culture. because that's truly what the majority. decides." [4]
On the importance of in-person connection for hiring: In the early days, Zatlyn and her co-founder made a point to meet candidates in person, which they believe contributed to low attrition. [2]
On the hiring manager's role: "Our managers spend 20 to 25% of their time recruiting, which is two hours every day or one day a week. It's a lot." [2]
On the value of a great team: "No matter how amazing you are as a founder, you need a team. You need a great team. A lot of smart people want to join a company making an impact."
On building a long-term business: "We've always thought about building a very long-term. business we want to build a big long-term. business so we were really thoughtful about this." [4]
On the importance of sharing the 'why': "Leaders should continuously clarify and remind teams of the 'so what' behind the 'what' they are executing on." [9]
On the power of a shared purpose: Zatlyn highlights the importance of small, dedicated teams united by a common goal. [15]
On not outsourcing hiring: "I just don't believe you can outsource it good people. we think there's a big difference between a great hire and a good hire. and great people want to work for great people." [4]
On the challenges of scaling culture: Zatlyn acknowledges the difficulty of maintaining company culture while experiencing rapid team growth. [4]
On the importance of diversity of thought: In a podcast, Zatlyn discussed the value of having co-founders with different perspectives and skills. [16]

On Personal Growth and Mindset

On dealing with doubters: "You don't need to win them over. Everyone comes around at some point, and your job is to keep winning on the field, gaining progress, gaining ground …, finding the people who do want to believe and be championed." [3]
On not taking rejection personally: "Just because other people don't see what you see, that's okay. Don't take it personally and I think that was really hard for me to learn." [17]
On self-belief: "One of the things that I've said to myself a lot along the way, especially on the dark days, is you've got to keep yourself on the field. You've got to keep yourself in the game." [3]
On work-life integration: Rather than striving for a perfect balance, Zatlyn advocates for making strategic choices and setting priorities to manage work and personal life effectively. [2]
On the power of trying: "If there's something you see you like, try it. And if there's something you see, you don't like, maybe, you know, just say, 'Hey, that's not for me. And I'm going to try it a different way.'" [17]
On the need for new leadership archetypes: "The world needs a new definition of leaders or what they think of leaders. So I feel like for all the women on the call, the time is now, people are looking for other types of leadership." [17]
On learning from mentors you don't know: "I'm a big Twitter fan...people also share their thoughts online and these people almost become your mentors. You don't even need to know them." [7]
On processing feedback: Zatlyn has learned to be selective about which feedback to internalize and which to disregard, a crucial skill for any leader. [14]
On the value of revenue: "We were really about the tech and all about the engineers and the cool tech we are building...But you know what's even cooler is revenue. Like, revenue is really cool." [17]

On Cloudflare's Journey and Strategy

On being global from day one: "For us, we were very global from day one...if you have internet property, we make sure it's fast and safe around the world. And that's a universal problem around the world." [11]
On the freemium model: "It's really good if you [can] figure out other business reasons why you need that free service that help make your business model better." [3]
On simplifying for success: In the early days, Cloudflare only sold in US dollars to avoid over-complicating their operations, a testament to their focus on prioritization. [11]
On avoiding the innovator's dilemma: Zatlyn has spoken about how Cloudflare continues to reinvent itself, even as a public company, to stay ahead of the curve. [8]
On the future of the internet and AI: She believes a new business model is needed to properly incentivize content creators in the age of large-scale AI crawlers. [8]

Learn more:

Lessons from Michelle Zatlyn, President and COO of Cloudflare

On Entrepreneurship and Getting Started

On Leadership and Scaling

On Company Culture and Team Building

On Personal Growth and Mindset

On Cloudflare's Journey and Strategy

Written by Antoine Buteau

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