Dickerson oversees the roughly 600 employees—based in Brooklyn, N.Y., though there are now offices around the globe—who keep the site running and growing. And unlike many tech-related companies, Etsy has an even split of men and women on staff.
In this interview with Dickerson for our On Leadership series, he talks about his path to being CEO, the challenges he wrestles with and why being an English major proved so useful in business. The conversation has been edited for length and clarity.
Q. What larger insights into people's relationship to work and creativity have you gleaned from running Etsy?
A. You hear the phrase “work-life balance” a lot. What we’ve learned from Etsy sellers, and what I’ve learned as a leader, is what people really want is work-life integration. It’s not really a 50-50 thing. It’s about being able to integrate those two sides of your life into a coherent whole.
We have many mothers and fathers, taking care of kids at home, who are making things and selling them on Etsy. One of the things we hear is that the flexibility to spend time with your family while doing something you love is really important.
Q. A big part of Etsy’s model is that people create goods that are unique. Across the retail landscape, have you seen a rise in consumers’ desire for uniqueness?
A. I think there’s a real fatigue with the sameness of mass-market retail. There was a time when everyone wanted to wear the same shoes, the same shirt, the same jewelry. We’ve entered a time where that fatigue means consumers want things that are different from what everyone else has. There’s also this renaissance in building and making really interesting, unique things. It’s an entirely different retail environment.
Q. Do you think that desire is new, or it just wasn’t satisfied before?
A. I think it’s a little bit of both, actually. The Internet was really a catalyst. As soon as people realized they can get things that are beautiful and customized and personal, it fed a desire for more of those things.
Q. How many sellers on Etsy do that as their primary job?
A. Eighteen percent of our sellers do it full time. But 74 percent consider it a business, even if they do it part time, so we don’t really equate full time with the level of seriousness.
Q. What do the best sellers on Etsy have in common?
A. The best sellers on Etsy have really great photography. They also tell stories about themselves, how they’re inspired, how they make the things they sell. Those are the keys to being successful on Etsy.
Q. What’s your biggest management challenge as CEO?
A. The biggest management challenge is always talent management, both bringing in new talent and developing the talent we have. New York is just as competitive a market as Silicon Valley, so I spend a lot of time personally recruiting and developing our existing employees. I really believe that if we have the right talent in place, we can solve any challenge that we come up against. The right talent is always, always going to give you a huge advantage.
Q. What do you see as your main goal, the one thing you ultimately want to leave to the company?
A. Etsy has been around for 10 years, which by Internet standards is pretty significant time, but we really want to build a company that’s around for generations. The long-term goal is to build an economy that really values people, values makers, values personal connections and things like authorship and provenance over just price and convenience. I see the opportunity for Etsy to create a new model for how commerce is done in the world.
We’re in an age where people have a hunger for belonging and meaning and connection, so I think our view of commerce can really play a role in that. We can use commerce to bring communities together, use the Internet to connect people instead of isolate people.
Q. What are your latest thoughts about the possibility of taking Etsy public?
A. I think about keeping Etsy as an independent company more than a public company. We serve a really great community and a lot of people depend on us to make a living, to deliver supplemental income. I mean, I’ve said in the past that being a public company could be an outcome for Etsy, but for me it’s more about the company always maintaining its independence and its point of view. Of course the company could take different forms in its lifetime to achieve that, but I think it’s really about independence and self-determination.
Q. What is the workplace culture at Etsy?
A. Etsy is very much a values-based culture. Employees really care about how we run the business and that we’re delivering social good. It’s also a really fun place. We have an annual talent show where you see everything from comedy troupes to bands to dancers. There’s this creative heart that Etsy has. You see it in the marketplace, but it very much exists inside the company as well.
Q. You took extended paternity leave while CEO. Did you see that partly as an opportunity to establish the culture of the workplace that you run?
A. Two years ago, my wife and I were going through an adoption process. And at the height of the holiday shopping season for Etsy, we got a call that said, “You have to be in Seoul, South Korea, on December 10.”
I had to make a choice about how to deal with building my family while also being CEO of a company that was growing really quickly. I really saw that as a moment to set the tone for the culture of the company, and also to set the tone for how I can be both a CEO and a father. It didn’t take me very long to decide what to do. I went to the board and explained that this was a really important event in my life and that I wanted to take the full paternity leave. I gave them a plan, and the board was completely supportive.
I’ve heard since then that it meant a lot to people inside the company. They actually saw me have a real choice to make and demonstrate what my values were—and what the company’s values were—through actions and not just words. That was a really, really important moment for the company, but also for me and my family. It was the best possible way that I could have spent nine weeks during that time.
I did an informal poll of other male leaders outside of Etsy. The thing that was really surprising was that many actually bragged about how little time they took off. You know, “I only took off a few days when my daughter was born, or when my son was born.”
I didn’t want people in the company hearing things like that coming out of leaders’ mouths at Etsy, because I think that’s really harmful. As a leader, you have to take care of your family—because that’s the base, in my mind, of how successful you are in your business. I’d love to see male leaders be more vocal about things like parental leave.
Q. Are there any other areas in which you’ve made a point to lead differently than you’ve seen your peers do?
A. One thing that was very different and frankly a little bit uncomfortable was my first annual review at Etsy. I decided to have a meeting with the executive team about the feedback. I didn’t have a private meeting with the board, or a private meeting with my executive coach. We actually did my review with everyone in the room.
It was an idea I had a few weeks before we did it. Then when the day came, as we walked into the room, I told my coach, “You know, this sounded like a much better idea three weeks ago.” But what I found was that it really solved a problem I had seen in reviews: All this feedback is gathered from colleagues, but the people who provide the feedback never hear you getting it, so in many cases they don’t know if you got it at all.
I found it was really helpful for the team that reported to me to hear me acknowledge some of the things that I needed to improve on. It closed the loop. Demonstrating the ability to receive feedback also shows a certain amount of humility. It was stressful going into that room, but it’s something that we do every year now.
Q. What have you been working hardest to improve in your leadership style?
A. Something I always work on, and it sounds really simple, is just being authentic. There’s kind of an idea in the world that CEOs are brash and dashing and loud. In fact, the night I went home and told my wife that I was going to be CEO of Etsy, the first thing she said to me was, “I don’t want to be married to a CEO.” And I think what she was responding to was this idea of what the CEO should be.
There are all kinds of pressures. On some days, people tell you you’re a genius. On some days, people tell you that you don’t know what you’re doing. So I’m committed in that environment, which is very up and down, to just remaining who I am. When I have to make a hard decision or I’m having trouble with something, I’m always recommitting to being authentic, being honest. That sounds very simple, but it’s super, super important.
Q. I think people are fascinated by how others have found success and moved up in their careers. So what you would credit as the main reason you are now sitting here as the CEO of Etsy, whether it’s a personal trait or someone who helped you or something on your resume?
A. I think it’s taking responsibility and not making excuses. When I’ve seen people struggle as leaders, often it’s because they’re saying, “I could do this if only this other person would do this.”
Throughout my career, I’ve always tried to take total responsibility. You have to be able to work with lots of people to be really successful. I’ve always asked myself, “What can I do to fix this situation?” Or, if I have a relationship issue with someone, I ask myself, “How can I make this relationship better?” As a CEO, one of the things that I’ve learned is that, by definition, to be successful you can’t make excuses. Whatever the problem is in a company, it’s your company.
Q. What’s a truth you believe about leadership?
A. There’s an idea that the organization serves the needs of its leader. I think that’s a really dysfunctional idea. The best leaders, the people I look up to, have an inverted model. They ask: How do I serve the needs of the institution? In a title sense, you’re at the top of the organization. But in a practical sense, you’re at the bottom looking up, trying to lift people up.
Q. Can you tell me about a mistake you made once that taught you a career lesson?
A. At a company I worked for many years ago now, I made a set of mistakes that snowballed into a situation where the company was, for a day, barely operating. I was working in technology, and when the technology’s not working, the company doesn’t work.
I remember feeling like I was backed into a corner. But at that moment when I felt most powerless, I realized I needed to stop worrying about that, go to the CEO, admit the extent of the problem and then put a plan together for how to fix it. It was one of those scenarios where you feel like you might get fired, but what I learned is still true today: People make mistakes. The real test is how you handle the mistakes.
The CEO didn’t fire me. He thanked me for laying out the extent of the problem. And I went and I fixed it. There were many people I could have theoretically blamed, but I didn’t do that. The handling of that was a big moment for me.
Q. What prompted you to respond that way? A lot of people probably would have defaulted to pointing fingers.
A. Taking responsibility is definitely something my dad taught me. When I was a kid, my dad would wake us up in the morning to chop wood to feed the wood stove in the winter. I remember one morning I was complaining, and my dad said, “Do you want to be cold?” I said, “No.” And he said, “Okay, well let’s get up and chop wood.” There was no magic to it. It was just that sense of knowing what you have to do and being no-nonsense about it.
In the case of the software system that was keeping the company from operating, I may have heard echoes in my mind of, “Do you want the company not to work?” And since my answer to myself was, “No,” I didn’t have time to fret. I just had to go into action.
Q. You were an English major in college. How do you think that has influenced you as a CEO?
A. It has been really influential to me. A liberal arts education in part teaches you storytelling. It teaches you how to write well. It teaches you the greater truths of existence. I focused on Shakespeare, and the reason Shakespeare is still so relevant today is because it’s timeless. In many ways, for a CEO, the things you learn in a liberal arts education are more relevant than anything else. And I got to read lots of great plays, which was awesome.
Q. Any leadership lesson you’ve taken from Shakespeare?
A. My lesson from Shakespeare is that human nature doesn’t really change over time. In “King Lear,” you see Lear trying to divide up his kingdom and there are all these different personalities. It’s not that much different than running a company. The vast majority of my time is spent dealing with human nature, and people’s desires and wants and needs.
Q. Since we’re having this conversation in Washington, I’ll ask what policy change you care about the most.
A. We really want to see a free and open Internet. It’s not so much a policy change as a desire to keep the status quo, which is an Internet with no toll lanes so sellers like those on Etsy can grow and thrive. I’ve been working on the Internet now for about 20 years, and I think it’s the greatest economic engine we’ve ever seen. I really don’t want the fundamental freedoms and openness of the Internet to be threatened in anyway.
Q. What’s the best piece of advice you’ve ever received?
A. When you’re hiring people, focus on culture and values even more than on specific domain expertise. Whenever I’ve made mistakes in terms of talent, it’s been because somehow I deceived myself into thinking that the talent we need is more important than the culture and the values.
Q. What was your first job?
A. When I graduated from college, I had no idea what I wanted to do, so I had two jobs. One of them was working at a Pizza Hut as a delivery driver. I met a lot of really interesting people, but it also helped me pay the rent. And as I was driving that car around delivering pizza, I had a lot of time to think about my career and my life and what I wanted to do.
There is no perfect ladder. Like John Lennon said once, life happens while you’re making plans. So that was just my life happening, and it was great. I thought about writing a novel at the time, and I wanted to call it Hut of Darkness.
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