Picture it: It's January 2012 — Pinterest's desktop product is growing rapidly, but the site crashes every four hours. “People were on call all night,” says Naveen Gavini, reflecting on the company’s early days. “We couldn't even have lunch in Palo Alto without the site going down and one of us sprinting back to the office to debug it.”

That’s how Naveen — who recently wrapped his role as Pinterest’s SVP of Products — reflects on his early days at one of the Internet's most storied brands. At the time, Naveen was 24 and self-described as “the kid who was obsessed with making a mobile app.” Now, in hindsight, he says the mobile transition seemed obvious, but in the moment it wasn't. If one thing was for sure, it was Naveen's attraction to Pinterest. From the moment he met Co-founder Evan Sharp, creator of the iconic dynamic Pinterest grid, he knew had to be on the team. “It doesn't matter what they pay me, it doesn't matter what I do. I’m going to learn so much from working here," Naveen says. 

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Pinterest was among pioneers designing a delightful mobile experience, which we now take for granted. Back then, it was a risky bet to shift from being just a website. “There were a lot of questions internally about whether we were making the right bet to ask our small team of 10 to 15 people to focus on mobile,” Naveen says. But that mobile bet is exactly what drove the future of Pinterest, now a leading image-sharing platform that hosts 463 million monthly active users (as of April 2023), placing it 14th in the world’s most active social media platforms.

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As one of Pinterest's first 10 employees, Naveen joined the team as a technical lead, fresh from his former role as a mobile software engineer at Yahoo. He'd already entertained the idea of starting his own company but knew he'd benefit from all the learnings tied to joining an early-stage team. So he took the leap. Naveen cared about one main thing: crafting the most beautiful, elegant mobile app. “I was obsessed with that problem,” he says. “Today, AI is the hottest topic, but 2011 was the start of the mobile ecosystem era. There were all sorts of startups trying to conquer it.” 

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As with many new ideas, adoption doesn’t always happen overnight. Such was the case for the Pinterest team’s usage of the mobile app. “Selfishly for me, I believed in it because I just wanted to work on building a mobile app, but it was a lot of hard work to prove even internally that those apps are going to be worth it,” Naveen recalls. Some of his most frustrating moments during this period when people within the company wouldn't the mobile product. But it all paid off in the summer of 2012 when 80% of Pinterest’s traffic had shifted from web to mobile. 

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A couple of years in, Naveen’s role expanded to building a team of people who would obsess over new “problems” in growing the best mobile experience. “How do you build a culture, within a very small mobile team, and the best mobile team in the Valley? That was my focus,” he says. From there, Naveen and his team developed obsessions in the form of features that pinners would love. 

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Teams that knit together, innovate together

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Naveen moved up the ranks — to Engineering Manager, Head of Product Engineering, then in 2019, to Head of Design & User Experience, a title he’d never anticipated but one that he embraced with humility. “As an engineer, I wasn’t going to out-design any designers,” he says. His lack of design experience is precisely what fueled his ambitions to build an immense collaboration — what Pinterest calls “knitting” — between design, engineering, and product. “My focus was never to lead the design team. I wanted to empower designers to redesign the platform or the service across all our platforms. And through the work, we built a lot of respect and trust.”

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In this first edition of Unusual's Bright And Early series, Naveen tells the story about the mobile shift, building the collaborative culture that leads to big breakthroughs, and the bumps in between.

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Chris Marty: How did you first get connected to the team at Pinterest? 

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Naveen Gavini: My strategy was to ask lots of friends and family about the products they loved. When I asked around about Pinterest, there was a type of cult following.

I tried every channel I had to meet with Ben Silbermann, the co-founder. I responded to head hunters and my friend who was investing: “Get me in the door.” I wanted to meet with Ben because there was something special about what they were building.

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Rachel Star: How did you think about weighing your decision and what were the key drivers that allowed you to get confidence in joining Pinterest?

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Naveen Gavini: There were three factors for me. The first was the team and the people. I knew that whatever I'm going to be doing, I was going to spend a lot of time with these people, so I need to really respect them and want to spend time with them. When the company's so small, I think friendship goes a long way because ultimately what you're building may not be successful, but at least you made some good friends along the way. 

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The second was that I could learn from these people as we build. My motivation was ultimately to start my own company. I viewed joining a company as diving into a deep learning hole. Where am I going to learn the most?

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I remember geeking out with Evan, who was a designer by background. We were just talking about really well-designed products and how they should make you feel when you use them. I just knew I had to work with this guy. 

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Number three was the idea itself. I wanted to be really passionate about spending my time on a day-to-day basis working on the product. When I thought more deeply about Pinterest and the idea of collecting and following your interests, hobbies, and passions, I thought there was an endless amount of ideas that could spin off of that idea — whether it was shopping, visual discovery, or search.

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I remember having those conversations with Ben really early on and saying, “This thing could take many, many shapes and forms.” 

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Chris Marty: You joined Pinterest as an iOS engineer before mobile became viewed as a massive platform for growth. It's fascinating that you went on to lead design orgs and product orgs, but in the very early days, we all hear that startups are chaotic and there's not a lot of structure or focus. What was life like for you in that first year as an engineer and how did you assign some focus to your day-to-day?

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Naveen Gavini: I think I have a very lucky story in a lot of ways and a story that a lot of people look at and go, that's amazing. When we made the bet to focus on mobile, we wondered, “Is this actually going to pay off or are we wasting our time? Should we focus on being a website?” 

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It was a lot of hard work to prove even internally that those apps are going to be worth it. Some of the most frustrating points of the day-to-day was that I would be working on stuff and even people within the company wouldn't use what I was building. I thought at the time, “I’m wasting my time because everyone uses the website; who's going to go use this mobile app?”

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That was really hard. Over time you have to believe that it's going to work and pivot along the way. The early days are so fun to reflect on, but in the moment they were so stressful. When you look back on it, you look back on it fondly. 

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Chris Marty: I think you're speaking of this mobile foray a little humbly. I'd love to hear more about that moment. In the months after that, that cemented this as a focus and then peripherally, how did you find that internal commitment and buy-in to actually working on this app? How'd you get others on board?

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Naveen Gavini: In spring 2012, we all sat down in Palo Alto and basically said, “We’ve either got to bet on this thing or we don't. … We dubbed it the “summer of apps” — everyone at the company was committed. It didn't matter what your job was, you got to support making these apps and get them over the line. That's what the final push was for us — it helped us catalyze and get those things out.

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I think it was a really well-timed decision that worked out because we launched those apps in the summer and within a couple weeks we saw more of our traffic go to mobile than web. Within two to three weeks we started to see 80% of our traffic come in over mobile and the remaining 20% over web.

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Instantaneously there was this amazing platform shift; it was just so well-timed with our growth curve that so much of our future growth was coming in mobile first. I think today we have the same sort of usage breakdown across platforms, but I think just the right time, right place, and a really well-timed decision.

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Rachel Star: You held a number of roles at Pinterest, leading the charge on mobile being the first of many. How did you think about managing your career and your path within the company? 

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Naveen Gavini: From the outside, the journey often looks like an awesome straight line, but there's always highs and lows. There's many times where I've considered doing something different, but what I've optimized for is just getting excited about the next problem.  In any high-growth company, what's really exciting is that there's no shortage of problems. 

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I can trace all the way back 11 years and think, What was I excited about? In year one, it was crafting the most beautiful, elegant mobile app. Fast-forward a couple years, and I started building a team of people who were obsessed with that same problem. That became my new focus. 

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Over time, I thought more broadly – not just a mobile app, but new features and functionality that pinners would love. I got obsessed with that for a couple years and led a lot of our consumer engineering efforts.

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After that I had the privilege of leading the design team. There was a new challenge at our doorstep: the design of our application across our different platforms was just getting so unwieldy that we needed to redesign our whole service. I knew that would be a really fun problem to work on.

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In my current roles, it's really been more about building a product culture and a company that people love to work at and can hire great talent and a brand that people really love and respect. In the early days it was caring about the pixels and now it's really caring about what the brand means to the world.

Rachel Star: What was it like to start your career in engineering and, later, lead design at Pinterest?

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Naveen Gavini: It was probably one of the hardest moments for me at Pinterest. Until that point, I worked very closely with our designers and there was a lot of love and respect and I learned so much from them. But I will tell you, it's another thing when you're announced at the company as the head of design and every designer is like, “I now report to an engineer, what the hell is going on?” 

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I also had to overcome that hurdle on a personal level because there was a lot of imposter syndrome. I knew I wasn’t going to fool anyone or out-design the team. What I realized over time was to focus on the things that I could offer. 

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My focus was never to lead the design team — instead, I focused on enabling and empowering the design team to be able to redesign the platform or redesign the service across all our platforms. And through the work, there was a lot of respect and trust that was built. I was never telling people how to design, but I was helping bridge that relationship with engineering and then get us over the hump on getting a project out that was very, very ambitious.

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Chris Marty: Pinterest is one of the first companies I think of as establishing a really core dynamic where eng, product, and design are seen as equals. Everybody has a seat at the table. There are many orgs that do well that can't establish that, and it's challenging. Are there any examples you can share about what tactical systems or processes led to achieving that equal footing?

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Naveen Gavini: Huge credit to the early team — Ben and Evan specifically. We had our original company values and we called it this value called knitting. Knitting is the idea that when you “knit” together different disciplines and truly understand their backgrounds and what they bring to the  table, your solutions are going to be far better because of it. When I think about the best teams I've ever worked on, people don't look at each other as, “you're the designer, I'm the engineer, you're the product manager.” All the disciplinary lines go away to focus on bringing the best solutions to the table. 

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What we did early on was really try to create teams in which we blurred those disciplinary lines. When I was working with designers, I would invite them to engineering reviews and have them critique the prototypes and push on them. And similarly, the engineers would be really involved in the design process. So the designer would basically design right next to the engineer and prototype together. It was this beautiful harmony. 

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This is what led to some of our biggest breakthroughs in design and user experience — the recognition that we can push each other to do things. Modeling that culture, it just progressed. A lot of our teams even today embody that interdisciplinary culture of knitting.

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Chris Marty: One more question that relates to your clear success in navigating hypergrowth as an early employee. For those who are thinking about doing the same within an environment where you have to find your next step and reach for it, what's your advice? How would you coach those to navigate the early days of a startup if their goal is not to leave in two years, but to make the best career for themselves at one place over time?

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Naveen Gavini: The journey that I went on at Pinterest was getting excited about a new problem every so often every couple years and really sinking into that problem and trying to learn and become the best at solving that problem. That same thing applies to anyone who's joining a company at any stage. But especially at a startup, there are so many problems. 

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If you were to tell me when I started that the 24-year-old me who was obsessed with making a mobile app would one day care about people problems, HR systems, and the brand of the Pinterest, I would've told you that you don't know what you're talking about. But I think if you have an open mind and are open to being presented problems, challenges, and can get excited about them, that's really what startups and a dynamic environment were all about. 

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This is the first edition of Bright And Early, a series of conversations with the earliest operators from the world’s most iconic tech companies. We often hear founders discuss how crucial their first hires are. These early hires help define the company's culture. They need to be doers and leaders who can prioritize ruthlessly. They often have an outsized impact on the company, and end up wearing multiple hats as the company grows. 

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• Listen to the Unusual Field Guide podcast version of this story: Naveen Gavini on growing from first mobile engineer to SVP Products at Pinterest

• Want to find out about the next edition of Bright And Early? Sign up for the Unusual Ventures newsletter for monthly tips, access to events, and more.

• Read Holistic Hiring for Hyper-Growth in Startups