Josh Silverman Bio

Josh Silverman is the CEO of Etsy. Previously he served as CEO of Skype, Shopping.com (an eBay company), and Evite. He’s chairman of ScriptEd Inc., which works to equip students in under-resourced schools with coding skills and creates access to careers in technology; and is on the Board of Directors for Shake Shack.

March 4, 2024

Behind the CEO Who Wants to “Keep Enterprise Human”

In our increasingly virtual world, it can feel like many of our lives take place remotely. When Josh Silverman took the helm at Etsy in 2017, however, he went against this technological grain, helping to usher in a new, distinctly human-centered purpose at the e-commerce company: “Keep Commerce Human.” In this episode spanning the course of his career, Silverman recounts the difficult choices he has made in keeping people at the center of business – and what following that ethos has meant for his personal and professional life.

Transcript

Ranjay Gulati:

Business leaders committed to running their companies with a deep purpose often have to tread tricky terrain. Their job is to navigate trade-offs among multiple stakeholders, including investors, customers, employees, and the community. These leaders are uniquely willing to linger in a space of discomfort, ambiguity, and contradiction, but they do so while staying as true as possible to their company’s fundamental mission. Hello everyone, this is Deep Purpose, a podcast about courage and commitment in turbulent times. My guest on this episode led a remarkable turnaround of the online crafts marketplace Etsy. Over a career marked with many innovations, Josh Silverman co-founded the online invitation platform Evite. He was a CEO who turned Skype into a global communication powerhouse. He also led shopping.com, and held executive positions at American Express and eBay. Josh Silverman says there have been multiple times in his career when he put himself at an inflection point between success, and as he describes it, abject failure.

Josh Silverman:

And that has been incredibly motivating for me. For example, I graduated from Stanford Business School and had a good, respectable job and decided that I wanted to start my own company. And at that time, everyone was doing stealth startups. No one was telling anyone what their business plan was, and I told everyone what my plan was. There were many moments when I was trying to get that company off the ground, what became Evite, where it was terrifying and it really felt like it wasn’t going to succeed, and it was very lonely. And the fact that I told all of my friends and family that I was going to go and pursue this very specific business idea meant that I had to move forward and make it a success because otherwise it was just going to be too humiliating. It was very motivating.

Ranjay Gulati:

When you say very motivating, isn’t… For many people, the possibility of failure elicits a different kind of emotional response. It elicits kind of the fight or flight, but the fear response, which is an hardwired emotion in us, primitively, in the primitive side of the brain. How do you turn fear into motivating?

Josh Silverman:

Yeah, I’ve had multiple moments in my life where I’ve really felt like my career was… I was at a tipping point where my career could very well turn on what happens in the next month, and for me, that’s really focused the mind. I remember when I was working for eBay and I convinced eBay to buy this company called Marktplaats and pay over 200 million euros for a classified site in the Netherlands because I thought it was a good idea. And then I took charge of Marktplaats, and we had this competitor that was the biggest media company in the Netherlands that threw all of its resources at it and I had to fly back to San Jose to tell Meg Whitman, who was the CEO of eBay at the time, “Remember that company we bought for all that money because I said we should? Well, we are about six months away from losing in that market.”

And that plane ride home from that meeting with Meg was really one of the scariest moments in my life. I thought if I can’t make something work in the next three to six months, I think my career might be over. And that was very focusing of the mind for, “All right, in that case, what are the few things that we need to do as a business to succeed?” And clearing out the clutter of what I’m hoping for and what my team’s hoping for, and all of the interpersonal drama and everything else just falls away. And I remember that it was a Sunday we had the flight. I called my team in Monday morning and I said, “The next six months is really going to be either some of the proudest times of our life or something very, very different. So we’re not going to talk about anything other than these few things we need to do to succeed together.”

And the team did an amazing job coming together, challenging all of the norms that had gotten us there. One of the great things that gave us permission to challenge a lot of existing beliefs and a lot of existing dogma, do things very, very differently to great outcomes. And that turned out to be a great success for the team.

Ranjay Gulati:

This is a great story. Thank you. Look back in your childhood or your past, is there something that made you think this way about difficult adversity, fear of failure? Were there people who are your heroes, who you emulated and from whom you may have kind of picked up this kind of way of thinking about dealing with adversity and impossibility?

Josh Silverman:

We all have things we’ve had to deal with in life. I don’t think I’ve met a lot of leaders who didn’t have adversity that they faced in childhood. So we all have different things. But my mother certainly is a powerful role model. When I was in my mid-teens, she bumped her leg in a store and it caused this very debilitating, we now call it chronic pain syndrome, where if you can imagine the feeling of your funny bone being hit, it’s like that 24 hours a day, 7 days a week for the rest of your life.

So for several of my teenage years, my mother was either in the hospital or at home dealing with that kind of agonizing pain and just trying to figure out what can I do to be helpful to her? Or if I can’t be helpful to her, what should I be doing to try to be helpful to try to serve? Maybe there was something in there and her toughness. And I never thought she would live to be 50 years old and she’s 82 right now. She’s also survived many other things. She’s quite remarkable and she’s tough as nails.

Ranjay Gulati:

Do you think it was something about the way she processed that and just kind of toughed it through, and in spite of dealing with a very debilitating situation that kind of made you see that people are able to stand up to difficulty?

Josh Silverman:

I don’t know. I’m not sure there’s anything that special about me. I mean, I think we all have different things we’re dealing with. But I think there’s maybe a learned behavior that having put myself in a very uncomfortable place and having that work out a couple of times has taught me that putting myself in a very uncomfortable place can actually be really healthy and really good.

Ranjay Gulati:

Courage in business and in life takes many forms, but it’s clear to me that courage is an essential characteristic in successful leaders. As I’ve said many times in this podcast series, true courage is not the absence of fear, it’s taking action in the face of fear. I asked Josh Silverman to describe just such a moment in his life. He replied with a story about the time he took on the CEO job at Skype.

Josh Silverman:

Well, I mean, I picked up and moved my family many times, including to Estonia in the middle of the winter, which took a lot of courage from my partner, my wife as well. We have been adventurous in terms of picking up and being willing to move to different places on…

Ranjay Gulati:

How do you get them to do that? I think that Estonia decision, you got the Skype job, and part of that is going to move to Estonia. I mean people most of don’t know where it is on the map. How did you process that decision even as individually and as a family?

Josh Silverman:

Individually it wasn’t that hard. Well, for me, it wasn’t. The heart and soul of Skype had really been with the engineering team in Estonia, and yet they’d always been treated as sort of like a offshore engineering… So I wanted to demonstrate to that team that I understood the value that they brought. And the best way to do that was to put my wife and family in Estonia and show them that I valued them as a team. My wife is very adventurous and she has been willing to put herself in uncomfortable situations. I think that’s one of the things that really attracted me to her is she’s very independent and she’s got a really global mindset, and she’s been willing to put herself in interesting positions too, just to stretch and grow. So most of the time that’s worked out. We did have young kids and the ability to move your kid from school to school put a lot of strain and stress on her. So that partnership between she and I has been a really important part. It’s been a team effort for sure.

Ranjay Gulati:

Do you look at… As you think about some of these decisions, do you think about… Is there a personal purpose or a mission you have come to realize for yourself? How do you think about legacy, meaning, purpose, spirituality, beliefs? How do those play a role into your thinking about operating as a courageous person?

Josh Silverman:

Yeah, for me personally, I do think you only get one chance on this Earth to do things and can you leave things in a better place than you found them? I do think that is a very important driving force for me. I’m very aware of the fact that my grandparents arrived in the United States as economic refugees with very little education and absolutely no money. They worked in the sweatshops their whole life. My dad grew up in public housing, and the public school system in New York City was able to lift my parents out of poverty and into the middle class and give me a ton of opportunity. So providing economic opportunity for other people has been a big part of what’s motivated me. It’s a lot of why I’m so passionate about the job at Etsy. It’s what I loved about working at eBay as well. It’s my work at Code Nation as the chairman of Code Nation. That’s been I think the consistent through line for me.

Ranjay Gulati:

Have you encountered cowardice ever?

Josh Silverman:

In myself?

Ranjay Gulati:

In yourself or in others? At one point, you talked about… In one of the interviews you did, you said that the typical reaction many leaders have to difficulty is they kind of freeze up, or even in yourself?

Josh Silverman:

Yeah, I mean, I’m sure I have all the time. First, there’s many opportunities I haven’t pursued for fear that I wouldn’t succeed, and who knows, maybe some of those would’ve been great successes. And one of the things that’s been very helpful for me is surrounding myself with a team of people I really trust and who trust me, both at work and at home, who can tell me, “Josh, I think this is important and you’re not moving fast enough,” or, “I don’t think you’re being bold enough.” And having those kinds of relationships with people who push me, who challenge me has been very important.

Ranjay Gulati:

Josh Silverman is an incredibly successful business leader in both launching startups and leading turnarounds of more established companies, but that’s not what Josh set out to do as a young man. Fresh out of Brown University with a bachelor’s degree in public policy, his first objective was Capitol Hill.

Josh Silverman:

I became very passionate about healthcare reform in college and decided that I really wanted to work on fixing the United States healthcare system. So I decided that I was going to work on the staff of someone in the Senate who worked on the finance committee or the House who worked on the Ways and Means Committee, a Democrat. Now each of those people only has one healthcare staffer, and they only turn over about once every three years. So that meant that there were maybe 13 jobs in all of America, positions that I was trying for. So I moved to Washington, DC after graduation and was sleeping on the couch of a family friend in the basement with no job, pounding the pavement, trying to get one of these precious few jobs.

Someone told me that Bill Bradley, a Democrat from New Jersey who was on the Finance Committee, had an opening for someone who was a foreign policy specialist who came from the state of New Jersey. And I told my friend, “I’m perfect for that job. Please get me the interview.” So they got me an interview and I show up, and the very first question I’m asked is, “Where in New Jersey are you from?” And I said, “I’m not from New Jersey.” “Oh, but you have a summer home. You have a grandparent.” I said, “Actually, I have to tell you, I’ve never been to the state of New Jersey.” The next question is, “Okay, let’s talk foreign policy,” and I knew I didn’t know anything about foreign policy, so I said, “I have to stop you right there because I don’t think I could find France on a map if the map wasn’t labeled.” And we’re two minutes into the interview and Mark was interviewing me, said, “thanks very much. It was nice to meet you, and John is going to take you to the door.”

And I said, “Wait, wait, wait, wait. Senator Bradley has no real position on healthcare, and I think there’s a real role for him, and he could position himself between Kennedy on the left and this senator on the right, and I think he could…” And we end up getting into a two hour debate about healthcare policy and the role of the senator. I mean, there were a couple of lessons from that from me. One, I had no plan B. If I did not get this job, I had no backup plan and I could still be sleeping on that couch in the basement today. And that caused me to be all in and so focused and so prepared. I was outrageously prepared for that interview. So there is something about putting yourself in that position where the only alternative to success is adjunct failure.

So two years after that, after I’ve been working for Senator Bradley, the chief of staff for the senator calls me into his office and says, “I’m going to Booz Allen and Hamilton to help start a healthcare practice, and you’re coming with me and I don’t want to hear any backtalk.” And I never heard of the industry of management consulting, I had no idea what Booz Allen and Hamilton was, but I’d worked really hard, and I think he was impressed by that, and that’s how I found myself in business.

Ranjay Gulati:

Wow, amazing. That’s a great story. Thank you. Now, fast forward a little bit. You’re working at ADAC, is that how you say it, ADAC Laboratories as a VP and general manager, and then you join Evite as a co-founder, CEO in 1998. That’s another big move. So now you’re going into kind of startup venture land, which is risky, inherently risky.

Josh Silverman:

So first graduating from Stanford Business School, I went to join this company no one had ever heard of called ADAC Labs, and I went to that company because it was a very, very well-managed, very entrepreneurial, very hard driving company where I thought I could learn a lot, and they were willing to give me an unreasonable amount of responsibility. I had one of the lowest salaries of anyone in my Stanford graduating class, I didn’t care what they paid me. I just wanted someone to give me a lot of responsibility. And because it was a smaller company that no one had heard of, they were willing to do that. This was 1997 and 1998, and the internet is starting to happen. So my best friend and I every Saturday bring two ideas for a startup, and he brings two, I bring two. And long story short, I come up with this idea to send… Called togather.com, to send g-mails to gather people together. How do we organize events and activities?

I was working 80 hours a week, so I had no time to plan an activity with my friends, but on Friday night at 9:00 I had time to go out. So I needed a tool to help organize something during the week so I could have a social life. So I quit my job at ADAC Labs where by that time I was running… I had like 50 or 60 employees working for me and a whole P&L and the whole thing. And I quit with no business plan, no venture cap, no venture financing, and no co-founders. Because I was working 80, 90 hours a week, I had no time to write the business plan. And I went into the CEO’s office and said, “I’m quitting.” And he said, “You can’t quit. I’m grooming you to be the CEO of this company, and let me talk to your VCs.” “I don’t have any VCs.” “Let me read your business plan.” “I haven’t even written it, Dave, I worked so hard for you. I have no time.”

That was incredibly scary, to quit my job with nothing, and the next day be that person sitting at my desk all by myself in my house, knowing the weight of all of my Stanford classmates who thought I was going to grow up to be somebody important, and I’m just this person now writing a business plan, and what if it fails? And as I’m doing my market research for this, I have all of my friends fill out surveys of how many events they’ve gotten invited to and what kinds of events. One of them said, “Hey, there’s this company called [inaudible], and they have this thing called Evite, and how do you compare to them?” And I was like, “Oh, someone’s beaten me to it. I’ve already quit my job. This is terrible.” Talk about fear. That was one of the most fearful nights of my life. I thought, “I can’t believe what an idiot I am. I’ve quit my job, I’ve put myself on the line for this, and there’s already a company doing it and I’m too late,” and man, that was crushing.

And a good friend of mine said, “Why don’t you call them up? For all you know it’s three people in a garage.” Sure enough, it was three people in a tiny little office focused on object oriented template language extraction, which is a tool they’d built to scrape websites to put all of your financial information in one place, and they’d built Evite as a little side project, as a contracting gig for someone, as a scheduling tool. Anyway, so long story short, we met, we took my business plan, combined it with their brand. They were a couple of engineers, I wasn’t an engineer, so we ended up forming an amazing partnership together.

Ranjay Gulati:

One of the things you’ve said in the past is every job I had was a job nobody else wanted. Speak to that a little bit and how that seems to imply somehow that you are taking on jobs that are inherently either risky, challenging, fearful, and is that by design or is it just circumstantial that you always somehow… Or you see opportunity where others see no opportunity? What’s behind that?

Josh Silverman:

I think there have been some moments where I felt like I saw a real opportunity where maybe some other people didn’t. I mean, an example might be Skype. eBay had bought Skype, and about a year after the acquisition it was clear that it wasn’t going well and the founders had left or been fired. So Skype at the time was about free phone calls. Telecom is a very highly regulated industry where telco costs were going to zero anyway. The culture was famously fracturous, and the eBay ownership was kind of fraught. And eBay took a billion dollar write down on the company, it was perceived as this company that eBay had overpaid for, and they spent months looking for anyone more qualified to run the company and nobody wanted to run it. I kept raising my hand and saying, “I’ll run Skype, I’ll run Skype, I’ll run Skype.” And finally they came back to me and said, “All right, fine. We’ll let you run Skype.”

And the reason that I really wanted to run Skype is I knew that Skype did really powerful things for people. Whatever the financials said, it had a really powerful impact on its customers in a really meaningful way, and it had a really talented team, even if it was fracturous. Now, eBay had also committed to the Skype team that the next CEO would definitely not come from eBay, which I did, would not be an American, which I was, and they would get a chance to interview and select the CEO, which they didn’t. So they were 0 for 3 on that, and that made my landing at Skype hard on the first day.

But the Skype team and I all shared a real passion for what Skype did, and it ended up working out great, and we got along really well. And what we did was we pivoted Skype from being about free phone calls to being about video calls, being about being together when you can’t be in the same room. And we brought video calling to mainstream at scale, and that created the next great inflection for the company and we ended up tripling the value of the company in three years.

Ranjay Gulati:

You say one thing, on courage in times of crisis, you’ve said in the past, many leaders get paralyzed in a time of crisis, but it’s actually incredibly liberating. When the only alternative to success is abject failure, it focuses the mind when staying the course results in the company not existing anymore. You’re given tremendous permission in many ways to [inaudible 00:21:30]. The risk of change has dropped tremendously. Say more about that.

Josh Silverman:

Yeah, I think one of the skills I’ve honed in the years and I think is important is the ability to define… You have been very successful because of some things and in spite of some things, and many companies that have been successful enshrine everything they’ve done as dogma and say, “We have to keep doing that.” So the permission to challenge those dogmas is very important. If I think back to Marktplaats, that was that company in the Netherlands that eBay had bought that suddenly had all the competition. There were a set of things that the company believed were responsible for its success, such as it only had one low res thumbnail image for every listing. And at the time that Marktplaats was formed, many people were on dial-up internet, so it was very important that the page load be very, very fast.

But the company had enshrined low res photos as part of its strategy, as part of its values. Obviously by adding high res photos and a lot more of them, we could make the site experience much better. The company had decided that advertising is evil and that they never wanted advertising, but we also charged for listings. Our competitor didn’t charge any money to list an item. So we said, “Well, actually advertising is a lot better than having to pay a fee, so let’s turn on advertising and make the site free.” And there were a bunch of those notions. When I said I came back from that trip with Meg Whitman, and in the next three to six months, we had to change a lot of things and do a lot of hard things in order to turn the company around. We challenged all of those dogmas and in the process actually unlocked a ton of value.

Ranjay Gulati:

When Josh Silverman took over the online craft marketplace Etsy in 2017, there were a lot of entrenched dogmas he had to challenge. Etsy saw itself as a company defined by its social purpose, its human-centered mindset, and a deep commitment to its employees. But Etsy had been losing money for years. Silverman took a comprehensive look at the company and set out to make it run better. It was a tough, stressful process. A lot of employees at Etsy felt betrayed by the changes and quit. But Silverman refocused Etsy, once again unlocking value that others didn’t see. You’ve in the past also said there’s often a lot of gold hiding under the sacred cow. As an Indian I like that metaphor. So one of the first things you’ve said that you did in the company is you look at their core beliefs and inspect whether the core belief is actually adding value or not adding value.

Josh Silverman:

So for example, Etsy said, “Etsy is about handmade, and therefore we should make each thing our ourself. So we will write our own customer support software. We will host everything ourselves.” And that is confusing a tactic with a strategy or a value. Those are tactics, not values. So asking yourself does that make the customer better for each of these things we talk about as values or as dogma, usually the way to know you’re onto something is when people are uncomfortable answering the question. If people feel like that’s not even a question you should be asking, then I’m interested.

Another part of Etsy was that the fee needed to be 3.5%. It was almost as though there was a tablet that said, “Thou shalt have 3.5% fees.” And when I asked people, “where did we come up with 3.5% is the right fee and why should it be 3.5%,” people said, “That’s core to our mission. That’s core to our strategy.” And I said, “That’s not an answer. Can you tell me again why 3.5% provides the most value to our customers?” Because when we raised our fees, which we did, we could invest a lot more back into marketing and into the site experience to grow the business on behalf of everyone.

Ranjay Gulati:

One of the things you did in Etsy as well, along with this great illustration, is you also interrogated the purpose of the company. And purpose has become part of your repertoire of things you think about. What does the word purpose mean to you individually and collectively for an organization and for an individual?

Josh Silverman:

I guess the simplest way I would describe it is what hole in the universe would this company leave if it wasn’t there? And if I can’t get comfortable that it leaves a meaningful hole, then I’m not sure I want to be part of it. So just starting with me, what do I find motivating enough to want to dedicate a good part of my life to something. With Skype the idea that we need to be together when we can’t be in the same room. When I arrived at Skype and we started talking to customers, that’s what I took away was we’re becoming a more fluid society where people live in multiple continents, they’re far from their family, they’re far from their friends, and we need to be able to be together. We need that sense of belonging even when we’re not physically present, and I think Skype could do that in a really powerful way.

With Etsy, it’s keeping commerce human. The idea that we’re more and more just at the end of this big global supply chain where everything is produced en masse, and we all feel like we’re just sort of anonymous consumers and becoming ever more commoditized and becoming ever more disposable. And I think people want that human connection. They want to feel like they’re directly connected. They want to feel like there are things made just for them, that make them feel special.

Ranjay Gulati:

Is it a rallying cry or is it something bigger than a rallying cry? Is it just for employees or is it also for customers, investors, other stakeholders? How does purpose create some kind of energy in an organization, if you will?

Josh Silverman:

It’s important that people feel connected to it because they need to feel like they’re part of something bigger than themselves. If it’s just about a paycheck, you’re never going to attract and retain the best people. We all want to be part of something bigger than ourselves, but more than that, if it’s not useful in defining your strategy and your product roadmap and your marketing messages, then I would suggest it’s probably just fluff. So keeping commerce human is something that we take very seriously at Etsy, so when we look at how do we compete with Amazon, for example, there are a set of things that are table stakes. Amazon is everything shipped in two days. I don’t think there’s ever going to be day when everything ships within two days at Etsy. That’s not going to be our strength.

But our strength is that the buying experience in Etsy needs to feel a lot more human than it does on Amazon. On Etsy, for example, we really encourage the buyer to have a convo, to have a message back and forth with the seller. Can you make this in yellow? Can you do it short sleeve instead of long sleeve? Most purchases involve convos between the buyers and the sellers on Amazon. The last thing they want you to do is send a message to the seller. That seller’s got to ship a thousand things today. They don’t want to be dealing with emails. So how do we make sure that’s our point of differentiation, is that Etsy feels unusually human.

Ranjay Gulati:

What does the purpose mean to you as a human being, and what is your purpose?

Josh Silverman:

Well, I want to be part of something larger than myself as well. I hope that my family will be proud of me when I’m gone. So most of my work has been around economic empowerment and trying to make sure… I feel very grateful. I start from a place of gratitude that I feel like I’ve been very fortunate to have the experience I have, to have the life I have, the wonderful family I have, and the professional experiences I have, and I feel like there is a duty for me to make sure that other people have that kind of economic opportunity, people from all different backgrounds. A lot was given to my family, we benefit a lot from that, and I want to make sure that I do my part to give back.

Ranjay Gulati:

You have said that there been periods in your life you had to reflect. You had moments of reflection, mini sabbaticals, and each of them, you have learned and grown. In fact, you say that you are not the person you were 15, 20 years ago. Do you want to say a little bit about your evolution as a human being, as a leader? Maybe give a little color to moments that were particularly important and impactful to you?

Josh Silverman:

Yeah. I mean, I think I’m a much better leader, I think, than I was earlier in my career, and I hope 5 and 10 years from now, I’ll say I’m a much better leader than I am now. I’m very much a work in progress. One of the biggest changes I think is I used to measure myself, or I used to think my job was to have good ideas and be a good problem solver. And I think I defined my contribution and my success as a leader based on how often do I have a good answer to that problem.

Now I really don’t see that as part of my role very often at all, and in fact, if I come up with the right answer to a problem, very often I start to get really nervous that I don’t have the right team or that people are just saying yes to me. My job is to define what success looks like and define what the constraints are and make sure that I’ve got the right people focused on the problem. They will come back with a better answer than I could have constructed almost all the time.

Ranjay Gulati:

How do you give other people courage? You have this courage instinct in you where you look at an adverse situation and you’re somehow able to say, “There’s opportunity in there. Don’t see that as adversity. See it as opportunity.” Even when you joined Etsy, what looked like an impossible situation, you turned it into an opportunity. How do you get others to think that way?

Josh Silverman:

First, hopefully, I mean, I try to surround myself with people who have a lot of courage as well, and I have a lot of… I’m very grateful to get to work with the very talented team I have, and they are brave and talented and wonderful people themselves, so I don’t think I deserve a ton of the credit. I do think expressing, verbalizing, “I have confidence in you” can go an incredibly long way. We talked about one of my leaders who I’ve recently asked to go take a turnaround job, turning around a business, and I think it meant something when I said, “I really believe in you, and I really believe you can do this job well.”

I didn’t promise a safety net. I didn’t say, “No matter what happens, we have a guaranteed home and…” I can’t do that. I can’t do that. So there’s still that level of fear, which I hope and think is probably motivating for her, but I really do believe that she’s the right person and that she’s going to do as good a job as… If anyone can fix it, she can. And I hope that’s been a support.

Ranjay Gulati:

One of the toughest things Josh Silverman had to do when he took the reins at Etsy was to lay off some 140 employees, and in the process eliminating activities that weren’t central to the company’s purpose. He changed the company’s overly verbose mission statement to a pithy credo, “Keep commerce human.” I asked Josh how he went about keeping Etsy human as he led it through such a challenging reorganization. How did he foster a business culture that connects being human, being kind, with holding employees accountable?

Josh Silverman:

Yeah, I’m proud of our culture because I think we do those two things together better than other places I’ve seen. We are a culture that really does believe in accountability. Empowerment comes with accountability. If you want an empowered culture, which we all do, you need to be accountable. So every squad at Etsy, Etsy’s organized by squads, and every squad is given one customer problem they need to fix with one financial metric it needs to unlock. So make this customer experience better in a way that unlocks this much GMS by the end of the year, would be an example of something we give a squad. And then they get to invent and decide how they’re going to do it. But every month we have a monthly metrics meeting, and every squad’s got to stand and deliver and say, “Here’s what we shipped last month. Here’s what worked or didn’t. And we’re this far to goal.” And it gives us a chance to track every single month how close are we to goal.

Now, it’s very rare for a team to be exactly on goal. Some teams are over, some teams are under. And it’s not uncommon that a team can be doing a very good job and miss goal. It might be that that customer problem turned out to be not that interesting of a customer problem, or it might be that they tried a lot of really ingenious, clever, bold things that happened not to work. If your team is trying bold enough things, many of them aren’t going to work. So I’m more than fine with a team trying. If they’ve got a good insight and they come up with bold ideas to address it and they don’t work, I’m fine. I only get nervous when it feels like we’re not being bold or we’re not starting from a place of customer insight.

But that accountability, I think, comes from that monthly metric meeting. And then I think we can hold each other accountable and never be disrespectful and still be kind to each other. And the more clarity we have around who owns what, the less we are each dependent on each other, the less politics there is. So I think also having an organization that’s relatively lean where there’s very clear ownership actually makes for less politics, and that makes it easier for us all to be rowing in the same direction.

Ranjay Gulati:

And what does kind mean in this? Is it kind in the way we communicate with each other?

Josh Silverman:

Yeah. I think people at Etsy are very respectful, want each other to win, are really rooting for each other. One of the things I hear over and over again from my teammates is every time I ask a teammate for help, their answer is always absolutely. People are really trying to support each other, and I think a lot of it is we all realize we’re in service of a larger mission. We’re all out there to try to make our sellers more successful. We’ve got 5 million sellers who count on us every single day to bring our A game, make the site experience better, so that they have more money at the end of the day to support their families.

And if we’re all operating in service of that, how can we partner together to get to the best outcome, and there’s no part of being a jerk or being aggressive that matters. The other piece of it, and I don’t want to be too gendered, but more than half of the company are non-males, more than a third of the engineering team are non-males. And I do think that has something to do with the tone in a really positive way.

Ranjay Gulati:

What’s going to be your legacy? What do you hope is going to be your legacy in this whole journey you’ve been on? What do you hope people will say and remember you for?

Josh Silverman:

I hope I’ve been able to have a positive impact on my community, and I hope we’ve been able to show that at Etsy we can be a great citizen and a great business, and that those are actually self-reinforcing.

Ranjay Gulati:

Josh Silverman is the CEO of the online crafts marketplace Etsy. There are many more of my in-depth conversation with top business leaders from around the world at my website deeppurpose.net. That’s where you can also find out about my book title, Deep Purpose. Companies that are serious about establishing and working towards a deep purpose find that it delivers game-changing results for the workers, the shareholders, and larger society. So visit with me at deeppurpose.net. This podcast is produced by David Shin and Stephen Smith, with help from Craig McDonald and Jennifer Daniels. The theme music is by Gary Meister. I’m Ranjay Gulati. Thanks for listening.