David Yee - From Startup Founder to Large Media Company VP of Engineering
I met David Yee, VP of Engineering at the New York Times through the LeadDev community through the LeadDev community where he recently hosted LeadDev New York where I spoke. As we talked, I learned more about his journey from startup exec to leading at a large company and thought we’d all benefit from hearing what he’s learned.
Leading at a startup is very different from leading at a growth-stage company or a large enterprise. When taking a leadership role, considering the phase of business is really important. It was wonderful to hear about his engineering leadership experience. We talked about what the transition from startup founder to big enterprise leader was like, being an experienced leader in a new organization, and what it means to “do the right thing” as a leader.
For people who don't know you, can you introduce yourself?
I'm David Yee, my pronouns are he, him. I'm a VP of engineering at the New York Times-I’ve been here for five years.. I've been a manager for a good long while, but I've been in engineering really since the 20th century, which is a crazy thing to say, but there we are. So I've made the transition from an individual engineer, experimenting with the web, to a working engineer, to architecture, to management, and through different modes of management and different contexts over the years. Right now I'm responsible for an organization at the New York Times that's responsible for how subscribers engage with the news.
In short, in my world, you'll find a lot of the New York Times mobile app and ways in which the New York Times homepage works. It's very product engineering focused, which is a lot of my history.
How large is the area that you oversee?
It's about nine teams and between 50 and 60 engineers, nine managers.
You've spent a good deal of time in startups, and have even founded one. Can you share a bit more about those experiences?
It's been several startups. The first startup I worked in was at the very stretched-out point of the dot-com bubble. So I count that as my entry into the work. But my more recent history with startups started around 2007, getting in at the ground floor with a few other folks to start a company called 20x200, which is a limited edition art sales site. I was able to see what it was like to sort of build something meaningful from scratch and something that made artists money.
I didn’t know much about the domain but got passionate about the product we built, and the people we served, and it was the first time I was able to build a team. So that was a really interesting moment for me because I went from this person who was just hacking things together to somebody who had to think about how you could bring a team to a problem. So that was my first experience leading at a startup. After that, I started a company called Editorially with my co-founders Mandy Brown, Jason Santa Maria, and Ethan Marcotte. We built tools for writers and editors. We were used by a lot of magazine writers and people who were working at media startups. I built a team again, but it was different because I was on the founding staff as the CTO. I was thinking about how we brought technology to the problem. What I loved about that company in hindsight now is that we were thinking as much about the kind of company we wanted to run as much as we were about the kind of product we were trying to build. That was really rewarding. It was a pivotal moment.
We sold the company to Vox Media. We were able to go into Vox and play in both of those spaces. Vox is venture-backed and was quite large when we got there, but still thought of itself as a startup. So we were able to keep building tools while thinking about how we wanted to run teams and build a culture.
I love what you said about founding Editorially and how you thought about the product and the kind of company you wanted to create. It’s an important distinction. Did you go into it thinking about the kind of company you wanted to create?
Yeah, definitely. There were a number of things. This was in 2012, we wanted to run a fully remote company. We wanted to be able to hire the best folks for the job, working anywhere. We wanted to think about transparency and clarity and how we communicated. We wanted to be very inclusive, bring people into the conversation, and talk through the kinds of things that can be hard to talk about: How are the finances of the company? How are things growing? Where are we struggling? That was really important to us.
What was your leadership philosophy like when you were in the startup world? Did you have one? Was it fly by the seat of your pants?
Yes to both but it’s also evolved. If I think back to my first experiences managing at 20x200, I didn’t have a leadership philosophy. But I think back to my first boss, David Lerner, from when I worked at a computer repair shop in Manhattan called Tekserve. He used to say, “Just do the right thing.” That's the number one principle. If you lose us money and it's still the right thing to do, then just do it. So I just kind of carried that with me. I said, oh, we'll just do the right thing. It's easy to do this when you're fixing someone's computer.
It's a little bit different in a giant product engineering organization when it's not really clear what the right thing is to do. What approach am I supposed to take to build this? Where is the web rendering stack going? What are the commerce implications? I don't know what this other engineer is doing. Is the founder gonna get mad? All of these things have implications and it's not always clear because the people don't have the context. I was sort of clumsy about it. I'd sweep it under the rug or I’d just sort of say I don't know, do whatever and we'll figure it out later. It was sort of haphazard because I wasn't thinking about management.
So that was my leadership philosophy when I started.
It started haphazardly but, spoiler, I did start thinking about it.
By the end of my time at 20x200, my role went outside the engineering organization. I’d been there from the beginning, so people looked to me for things. I realized I had to take it seriously. Then at Editorially, it was about how you run a supportive company. How do you guide somebody in their work? How do you talk to them about their work? How do you lead them in their work? Then you get into situations where two engineers aren’t getting along and trying to troubleshoot that. Giving people the agency and autonomy to solve interpersonal problems in a way that gives them agency, but also responsibility to come to the correct conclusion for the team.
By the time that we took that to Vox, it was pretty set and then we’re integrating with a company that didn’t do remote at all. So we had to introduce them to remote work without being in the driver’s seat, so it was more influencing from the side.
Then it was how are we going to adopt what we need to adopt from them and then also push them in different ways? That worked out over time as, in the end, Mandy and I both being in positions where we were driving different parts of the culture alongside people who had driven the culture there for years. It was a really enjoyable experience to figure out how to scale up what was a fairly small model of running a company to something more substantial.
What was the transition like as a leader when you moved to a larger company?
Scary. Awkward.
I was working at a company that had like four engineers. This company had 30 or 35. It was just like a very different model. I was like, “well, they clearly have this figured out.” People were writing about them in the media space. They were doing exciting stuff.
The day we started, Vox was holding its annual hackathon in Philly. We took the train to Philly, the three of us, and we show up and there are all these people sitting in a room and they're just like silently building stuff, they're listening to music and they're working on their computers and they're occasionally making inside jokes. We don't know anybody. I don’t know what to build. I don’t have any context, so I kept walking up to engineers saying, like, “Hey, I’m David.” It was like being the new kid in school except like you come in and you're like you're sort of like well, am I the new kid? Am I the new teacher? I don't know what I am.
Those first couple of days were disorienting, but Vox was a very welcoming organization. I can't think of an example of a startup acquisition that felt as smooth and as healthy as ours, but we did have to learn a lot. We interviewed like 90 people in 90 days and got to know the team. I built a very close relationship with a couple of engineers there who were embedded in our team. I did a lot of on-call work to understand their legacy system. I really tried to walk the walk. I think it helped me understand them and I think it helped them understand me. You know, we were very fortunate. It went, ultimately it went really well, but those first couple of days, it just felt disorienting. How could there be so many engineers?
I think we have this tendency to think leaders can lead anywhere but leadership during the startup or scaling phases is really different than the maturation phase. I love that you're speaking to these differences because leading in different sizes and complexity of cultures. They're quite different. It's a different job.
That's completely true. These were all fundamentally different skills that I was leaning into.
In this culture, we can’t really speak flippantly about moving fast and breaking things. There’s a greater impact of mistakes. So the decisions were different. The risk is different.
So you ended up going to the New York Times. How much did you consider the culture before you took the role?
In different ways, a lot. So the story of me going to the New York Times, I met Brian Hamman, who would hire me and be my manager for a long time, at a conference called SRCCON. Brian and I got to talking there. I liked him, the way he thought, I liked the way he communicated. I was like, well, I didn't know anybody else at the New York Times, but this guy seems nice. I wasn't thinking of a job at the New York Times at the time but through him and a couple of other folks, I understood what it was doing as a product and what it was doing as an organization.
I've worked in media in a few different contexts, and this was the place for journalists where it was the pinnacle of their careers. Some people work their entire careers to get to the New York Times. There is no greater organization than this. So I understood the significance of it. Then through the interview process, I inferred the edges of some things they cared about, like cross-functional work. I understood that they cared about my technical acumen, but that they ultimately cared about how I thought about decisions and how I arrived at decisions. So through the interview process, I was able to get a skeletal image of the culture by seeing how an organization presents itself to the outside world and the conversations you have with people inside.
I love that. When you got there what was the gap between that culture and the one you’d been in like? Were they quite different? Were there, you know, what was that Venn diagram, you know, of overlap there?
Vox Media was a newsroom built on top of a product engineering organization. The product engineering organization was the foundation and the newsrooms were built on top of that, which meant that everyone looked to the product engineering organization to say, well, this is possible, right? So you had a culture that emerged from an engineering mindset (for better or worse at times).
The New York Times is well over a century old, like 180 years old, depending on how you measure it. That newsroom has done so much and it's built up a culture of its own that is incredibly complex. Over the years, it’s developed a real sophistication of decision-making that is reflective of the way that the organization has had to adapt to the world to become what the Times is. So, in contrast with Vox, the New York Times is a newsroom with a product or engineering organization built on top. That means the product engineering organization has to look to the newsroom to say what's possible, but also what's not possible.
The guiding precepts of that culture are very different. A newsroom has to balance risk in a unique way. It's like, we as a newsroom have to be quick, but we can't make a mistake.
In this culture, we can’t really speak flippantly about moving fast and breaking things. There’s a greater impact of mistakes. So the decisions were different. The risk is different.
It's fascinating because even though both are in the media space and they’re bigger than the startup you were at before their approaches are opposite.
The New York Times also has a much larger engineering organization than Vox did. When I walked in the door, it was 10 times the size. It’s a total shift in the way belonging works and a dramatic shift in what it means to do the right thing. Like, in what context is the right thing the right thing? There are a lot of different contexts at the New York Times in which to do the right thing, many of which can be diametrically opposed. And that wasn't the case in a smaller organization or at least it wasn't as evident.
I remember talking to my coach soon after I joined. I was like, I don't know if I belong here. I don't know if I can operate inside this kind of company, and I'm trying to figure out how to change it. She asked, “In what ways do you want to change the Times? In what ways do you want the Times to change you? And what lies in between?” I've carried that over the last five years of my work.
There can also be tension between the kind of leaders you want to be versus the style of the company. How did you negotiate that difference?
I talked about the disorientation of joining Vox. That played a role at the Times too. At Vox I was a Director, managing managers. It can be lonely, and I just wanted to get back to principles and see what it's like to operate those principles on an engineering team and try and influence from the side and build a team from scratch-going back to what I did at Editorially. I got to go and hire what I needed. I got to work closely with a product manager building a parenting product for the Times-it was like building a startup. I was able to operate the way I wanted to operate, I thought. But it's not like that, right?
At work, I talk a lot about pirate ships. When you're a startup, you're a pirate ship. You can run raids on large tankers and you'll sink or swim under your own power, right? You have to get the treasure on your own. The reason you join a larger organization is that you have a lot more support. But with that support comes rigor in a lot of ways.
So here I am at the New York Times. I think I'm on a pirate ship building a startup product, as part of a team called New Products and Ventures. Nothing could sound more pirate-y than “ventures”. I'm doing it my own way. I'm going to the engineering management group meetings for the whole organization, which at the time was about 12 managers. I'm sitting in the back of the room, I'm leaning back in my chair, and I'm like, yeah, I know about career ladders. I know about remote work. I'm thinking they'll look up to me because I'm the new guy, right? I've come from this cutting-edge media startup and I know about all this stuff and I've spoken at conferences. And you know what? It just fell flat. No one cares. Maybe they cared in an abstract sense, but it's like, “well, okay, new person, what did you do there?” It was humbling.
What I felt keenly at the time was: “Why are decisions so hard?” Even something as simple as Slack, I was like, “Where are people talking to each other?” It turns out that the organization that I joined was much more complex. It was full of private slacks. I had never been in a place that was full of private slacks-I was used to everything just being out in the open, all in one central channel. It's easy to do when your whole organization is like a hundred people, right? But this was different. I remember thinking, “I don't feel connected to the organization.”
Then, thinking about how words are used: We were building something as part of NYT Parenting and trying to name it. We said, “Let’s call it a guide”. A designer who’d been there for many years said, “You can’t call it a guide.” There was some other product that was called a guide. So words were loaded because someplace in the organization there had been a product that used that word differently, something very specific to a very specific moment, so you can't reuse that word.
I remember talking to my coach soon after I joined. I was like, I don't know if I belong here. I don't know if I can operate inside this kind of company, and I'm trying to figure out how to change it. She asked, “In what ways do you want to change the Times? In what ways do you want the Times to change you? And what lies in between?” I've carried that over the last five years of my work.
As my career unfolds I think very carefully about when I’m right for the job. When am I right for the job? What do I need to learn? And how can an organization benefit from hiring me?
I love that you talked about organizational history and how as a leader you have to figure it out. It’s so true. Have you redefined what it means to be a leader?
I have not changed the leader that I am. That's what's shocking to me.
The way that I'm redefining leadership is being who I am, here at this place. I have an obligation to the business and I have an obligation to my people and I'm doing it in a specific way. Not everybody works the way I work and not everybody understands the way I work. but I still fundamentally lead my way. I try to lead with an emphasis on autonomy and a focus on bringing the right skills for the problem that you're solving. Curiosity and inquiry are really important to me. I'm changing by example. But you know what? At the same time, some of the colleagues I value and have valued most at the New York Times are people who work in a profoundly different way from me. I can't work your way, but I'm very glad you can.
It brings me back to that question of how I wanted to change the Times and how I wanted it to change me. If I only want to change my new context or I want my context to just change me. Neither of those things is going to work in isolation. I'm not going to really change and there's no way I'm going to change a culture that's over a century old. That's not going to work. I've found that tension in the middle and I've found that middle ground.
In the past, I used to characterize myself as an “inveterate agent of change”, somebody who's just going to like turn all the dials to 11. I'm going to shove the thing off a cliff and I'm going to build a new one. You're not thinking about the context, the people, or the problem.
As my career unfolds I think very carefully about when I’m right for the job. When am I right for the job? What do I need to learn? And how can an organization benefit from hiring me?
What advice might you give someone who's making the shift, some of these shifts from sort of startup to enterprise, or an experienced leader coming into a different culture?
Just ask “Why?” If you walk into a place and you say, “this place is bonkers,” and stipulate that it has to change, ask why it is this way. Why do people make decisions this way? Why can I not do this? Why does the newsroom think this way? What is the relationship that this executive has with this executive? Find the hidden threads.
This writer named Priya Parker wrote a book called The Art of Gathering. One of the things she talks about is the notion of “etiquette”-not in the sense of which spoon to use, but the unwritten rules that, once understood, give you access to power. I couldn’t care less about power, but almost every organization has etiquette. Understand the etiquette of the organization.
One last thing. I had a lot of control early in my career at my first startup. I had a lot of control over the code as an engineer. I didn’t realize it but when I look back I see I had a lot of control. I had a lot of authority over my work. I'm a VP of engineering now. I don't think I would be the only VPE to tell you that I have shockingly little control over the work.
I love that distinction because I think as we go up in our careers, we think we'll have more control. Given the complexity of organizations, in many ways, we have less control. I think it's a surprise to a lot of us when we get into senior leadership.
Yeah, you're collaborating across boundaries that are fraught, and you're managing through directors and managers who have their own values and their own need to be able to understand something about their domain. That's something I wish I understood earlier in my career.