The Reuben Mark Initiative for Organizational Character and Leadership & Strategy recently hosted the C-Suite Conversation Series with Etsy Leadership & Strategy, which offered a unique view into the inner workings of the C-Suite to understand how they strategically work together to drive an effective organizational culture.
CEO Josh Silverman, CLO Colin Stretch, and CHRO Toni Thompson spoke candidly with Professor Adina Sterling about how their symbiotic partnerships, with emphasis on human connection and adaptability, align and inform the greater vision and values of Etsy.
Watch a video of the event above, or read a transcript below:
Olivia Haynes: Hello and welcome everyone. We are going to get started right on time because we have an amazing panel for you today. My name is Olivia Haynes and I'm the Co-director of the Reuben Mark Initiative for Organizational Character and Leadership & Strategy at Columbia Business School. It's my absolute pleasure to welcome you to our premier program, The C-suite Conversation Series with Etsy Leadership & Strategy.
This event is hosted as part of the Reuben Mark Initiative at both Columbia Business School and Columbia Law School, which designs courses and programs to teach the Leadership & Strategy skills necessary to create optimal organizational cultures. This initiative was established by Reuben Mark, former longtime Chairman and CEO of Colgate-Palmolive.
Reuben was a visionary leader with a penchant for strong organizational Leadership & Strategy across all functions of the business. We are incredibly lucky to have his thought Leadership & Strategy and continued support for programs like this, and we thank him immensely. We're excited to get started today because our panel offers a unique view into the C-suite, helping us understand the inner workings of how these top leaders think and work together. The conversation will highlight the competitive advantage that exists when these partnerships are strong and symbiotic to help strategically design and effective organizational culture across all function areas.
With that, I'd like to introduce, there we go, our amazing moderator for today, Professor Adina Sterling, the Katherine W. Phillips Associate Professor of Business here at CBS. Professor Sterling is an absolute rockstar and we were so lucky to welcome her here this year to CBS after her long tenure at Stanford.
Her research advances in an understanding of how inequality persists in labor markets and workplaces. Despite the efforts of many leaders to create fair and equitable organizations. At CBS, she's teaching a cornerstone course entitled Equity by Design Building Diverse and Inclusive Organizations, which teaches our students about workplace systems, structures, and culture to identify and address inclusivity pain points.
Professor Sterling received her PhD in organization and management from the Goizueta Business School at Emory University. Prior to academia, she worked at Proctor & Gamble as a senior engineer developing consumer products.We are so grateful to have her here with you today and all of you and our amazing panelists. So with that, I'll pass it over to Professor Sterling.
Adina Sterling: Thanks so much, Olivia, for the warm welcome and welcome to all of you. We are very excited to have a conversation today with Etsy C-suite. It's not often that we have three leaders from the same C-suite with us to talk about not only their own Leadership & Strategy style, but how they work together as a team and how they drive the business forward. And so, again, welcome to students, faculty, and staff from the Business and Law schools. We're excited to dive in. I will just mention that Olivia, with that long introduction, mentioned that I'm the Katherine Phillips chair.
I'm actually the inaugural Katherine Phillips chair, which I hold in very high esteem and regard.
I knew Kathy Phillips before she passed away, sadly in 2020, but this is really a full circle moment because the Reuben Mark chair was held by Katherine Phillips, Kathy Phillips when she passed away. And so this really is a special moment for all sorts of reasons. And I'm excited about the journey that we're going to go on in the next hour.
I think that deserves a round of applause. So I'm going to introduce each of our esteemed panelists quickly. And then after that, the question that we'll kick off with is what three words describe your Leadership & Strategy style? And so you can noodle on that a bit as I'm doing the intros.
So I'll start with Josh Silverman, who's the CEO of Etsy. In this role, Josh leads the company as it builds a platform that empowers creative entrepreneurs around the world. Josh is no stranger to growing consumer technology companies and scaling global marketplaces. He served as President of Consumer Products and Services at American Express. He was the CEO of Skype and the CEO of shopping.com. And earlier in his career, he co-founded Evite.
Next, we have Toni Thompson, who's at the end, Chief Human Resource Officer at Etsy. Toni advances Etsy's high performing equitable and inclusive culture at Etsy and shapes how Etsy approaches the Edge. She served as Etsy's Vice President of Talent and People Strategy, and prior to joining Etsy was the Senior Vice President of People and Talent at the Muse and held HR Leadership & Strategy roles at Condé Nast.
Finally, we welcome Colin Stretch, Chief Legal Officer of Corporate- Chief Legal Officer and Corporate Secretary at Etsy. Some of you may recognize Colin for his recent roles as Executive-in-Residence at CBS and Leader-in-Residence at Columbia Law School. Prior to Etsy and Columbia, Colin was General Counsel and Deputy General Counsel of Facebook now Meta. He also clerked for Justice Stephen G. Breyer on the US Supreme Court.
So let's welcome our panelists. Again, we're so thrilled to have you. And yeah, let's kick it off with three words that you would use to describe your Leadership & Strategy style and and why those three words come to mind.
Josh Silverman: Happy to start. Hey, well first of all, thank you for having us. It's delightful to be here together and I'm also really excited to spend time together with Colin and Toni 'cause we have not done a public speaking event outside of Etsy. And I think also we get asked a lot of the same questions a lot of the time when you go to the same events. And these are a very different set of questions. We haven't talked about this topic together, so who knows what's going to happen. And that's an adventure and fun to see it unfold. We'll figure it out. If I had to pick three words, I think disciplined, adaptable, and human.
If I elaborate, disciplined, I think what you're trying to do is get some insight into our culture and how things actually work at Etsy. And we're, for example, a very big pre-read culture. It's very important that I get information at least 24 hours before I'm in a meeting because I'm being asked to make decisions usually in that meeting. And earlier in my career, I would find that I'd make decisions and then after I'd leave the meeting, I'd think, oh, there were three questions I have that I didn't think to ask or someone would approach me with a different point of view. And we didn't have that person in the room. We weren't hearing all the diverse perspectives.
And so getting time to think about it, ask the right questions, make sure you have the right people in the room to make sure you're hearing all the points of view requires preparation. And I think as a Leadership & Strategy team, we all show up prepared. It is expected and our team should expect that of us, that when we're in the room, we've done our homework. And frankly, you know, at at Etsy we've got 6 million sellers, they are counting on us to bring our A game. And so they deserve that when we make these decisions, which are really important decisions, we're not winging it. You know, we are thinking about it, we're bringing data into the discussion. So I think discipline and preparedness at Etsy is a very important thing for all of our leaders. And we need to role model that.
Etsy's mission is keeping commerce human. I think you get the most out of your team when you're an authentic leader, or at least it's been my experience that when I'm vulnerable, when I'm authentic, people can relate better. And also they're much more willing to tell me things I may not want to hear, which is very important to making good decisions. We all have to be honest with each other. And so I think recognizing the humanity in each person, meeting people where they are, is something that I think we all try to do really well at Etsy.
And adaptability, and we might talk about that a little more, but you know, I feel like it's been seven years almost at Etsy and we've been through at least three very different chapters. And what it takes to succeed today is going to be very different for us as a company than what it took to succeed three years and five years ago. And that's on us as leaders to be able to adapt.
If we're going to adapt our culture, we need to be adaptable ourselves. And so I think it's a journey we're on together.
Sterling: Great.
Colin Stretch: My turn.
Sterling: Sure. Colin, go for it.
Stretch: First, thanks for, thanks for having us. I'll echo what Josh said. I've been looking forward to this and it is nice to be back. So three words that define me as a leader, I would say, well, these are aspirational.
One of my favorite Leadership & Strategy quotes is from Reed Hastings who says, if you want to be a be, if you want to be a better leader, be a better person. And I think that's a nice way to think about the sort of effort at sort of reinvention or at least development it takes to, to, to be effective as a leader. But I'll echo some themes that Josh said. I think openness, authenticity, and decisiveness. The first two for me, sort of go together. But it echoes Josh's point that you need people to tell you what they think and if you're not open to it, they're not going to. And if they feel like they can't trust you because they don't know you, they won't share with you what they really think. And if you're not getting good data, you're going to make bad decisions.
So that openness is really, I think, core to, to effective Leadership & Strategy, at least in a company setting. And then you've got to be willing to make decisions. The issues don't come to you unless they're hard. And if you're making too many easy decisions, you're either not thinking about 'em hard enough or you're not using your time effectively. You need to be able to make hard decisions and encourage your team to bring those decisions to you and and to be able to make the easier ones on their own.
Sterling: Great. Thanks. Toni.
Thompson: Also happy to be here, and we do do a lot of pre-reads, so this is not lying about that. It's good though. It's good. We're very prepared.
I would think my three, that's a good question. I think it's adaptive. So I tend to adjust my style depending on the readiness of the team to handle whatever task at hand. So if I think the team is prepared to handle certain challenges, I'll be really hands off. And if I think they need a lot more guidance, I'll be deep down in the weeds with them, depending on the situation.
Inclusive, I think there's a lot of value in having the right people in the room and giving them permission to participate in the conversation. I think leader leaders are critical in inviting people
to the conversation and pulling people's voices out of them. And transformational. I spend a lot of time talking about a phrase that Etsy called Start With Great. So I spend a lot of time talking through what the end's going to look like so that the team can put their brain against how we're going to get there. So that's what I'd say.
Sterling: Great. Wow. And I can, I can tell that you all work together because your answers were very complimentary and there is a lot of cohesion and synergy across those. So now we want to turn and dive into how you work together as a team and what that looks like. We already got great insight about the pre-reading that happens prior to meetings, but what do you think it takes to turn a group of C-suite leaders into a team, into a collaborative team, and how does your team work together to set and accomplish goals at Etsy?
Thompson: I'll kick it off. You know, we're a team like any other team you may be on. Debate team, sports team, and teams need practice. You need a lot of time together. You need to carve out space. And that's not easy to do when you're in the grind. You're focused on execution, you're focused on the metrics, you're focused on getting the stuff done. And so it takes a lot of intention and we put a lot of time and intention around how we carve out space for one another and have conversations around what we value in a team environment, what we want out of each other as teammates.
We've actually formed some operating questions for each other. Things like, how in sync are we right now as a first team? And those questions allow us to, they give each other permission to name when we're not in sync, which is really a hard thing to do. You don't want to interrupt the flow of a conversation to say, hey, I think we're really, we've been misaligned for three meetings in a row now. And so having these questions gives a little bit of a shared language in a shorthand.
But I use that example to say that my point is that it really takes a lot of intention and care and I think Josh really carves out a lot of space because he actually cares about it. And it sets the tone for, for all of us to lean into the conversation when the space is given.
Silverman: And you know, actually you used the term their first team, but we had a conversation just two weeks ago about who's our first team. You know, if you're running marketing, is your first team the executive team or is your first team, your marketing team who reports to you? And we all agreed together we are each other's first team and then the teams who work for us are our second teams. And that's not derogatory in any way. It's simply that if we as an executive team can't agree, we are delegating to our teams to fight it out amongst each other. And so it's really critical to our teams that we are well aligned as a group. And we had that conversation together. And then we talked about, well what flows from that?
It's easy to say things, but how do you go from say to do? So like where are we going to sit together when we're all in the office together? How are we going to use our time when we're all, we don't all live in New York, but one week a month we carve out time to be in New York and how should we use that time when we're together? Should you know each of us be with our own teams or should we be with an executive team? And how do we find the balance? And it takes a lot of discipline and preparedness. It turns out to actually map the calendars and take the time. But you know, last night we had a really nice conversation over dinner. So pulling back, spending time together, socializing the esprit de corps, knowing each other, knowing what's going on in our lives turns out to be very important.
We have to trust each other and trusting each other comes from really knowing each other. But one of the conversations that came out over dinner that I was really happy with was like, if we all fired ourselves tonight and came in tomorrow as our first day on the job, what would we observe and what would we do different? We're challenging each other with that. And constantly being comfortable enough with that to challenge each other is important. It may be interesting for this audience though, if I take a second to talk about our operating rhythms, from top to bottom. 'cause I also think that's kind of interesting.
So we twice a year go offsite and we talk big picture strategy, what's happening in the market, what's happening with our competitors and what are the most important things for us to do. The main thing is keeping the main thing, the main thing. So what's the main thing? Twice a year, typically March and September we go off and we think about big picture things. We from that agree on our most important objectives and who owns what. Many things are shared and collaborative and it's important that they be shared and collaborative. But it's also important that we just name who's the single person who ultimately is going to be accountable for this. We then have a monthly metrics meeting where every single month we get together and we look at are we on track, are we on plan to what we just said?
And then weekly we have our executive team meeting, which is a kind of formal meeting where we're making more formal decisions and people are bringing data in. But twice a week we have what we call standups. It's just time to be a team and that's team time. We typically don't have agenda items and that's where we talk about what's happening in our daily work lives. And I think there's more of a chance for us to build esprit de corps and trust in team. And so from sort of top to bottom, we are trying to have time both for sort of strategy and execution and esprit de corps and, and carving out time with intention for all of those things I think is important.
Stretch: Can I just add one so? First I'm happy to report that after we were all invited to fire ourselves last night, my badge worked this morning. So that was some degree of relief. You know, we're a team. It's true. And we're a first team. And I just want to emphasize, we're not a team of equals you know, we work for Josh. He's our CEO obviously. And how, and I'm going to say something nice about him, but not just 'cause it's bonus season.
The way he sort of models team Leadership & Strategy matters and it matters not just because it makes our team more effective, but it, it sort of teaches us what values we need to bring with our own Leadership & Strategy teams and with our own teams further down in the organization. And I'll mention three things and they're somewhat concrete that I think he models day after day that really make a difference to the function of the organization.
One, and he said this earlier, but do the work. No one is deeper into these decks and I mean, we're joking about the decks, but you should see the one for this meeting we have tomorrow. It takes a lifetime to get through. And yet, you know, you get to page 178 in the footnote and there's Josh dropping a comment that is like incredibly detailed and somewhat intimidating.
So he does the work and that's a great example to all of us. And a great example to the company that he is deep into the details.
He listens first. So whenever we talk about anything hard, he doesn't say what he thinks even notionally until everybody else has a chance to speak. And I'm sure a lot of you have heard, you know, or witnessed in your prior professional experiences the virtue of that. But when a leader comes into the room and says, hey, I'm going to tell you what I think, what do you all think? Well, what do you know? Turns out everybody thinks the same thing. Like you don't get the same, you know, open discussion if the leader spouts off first. And he never does that. I've never seen him shut off discussion that way, which is I think great for us as a team. 'cause it empowers us and I think leads to more robust discussions.
And then the third thing I'll say is transparency. You know, if it's on his mind, he doesn't know exactly what we're doing every minute of every day. He doesn't really know what the information he has in his head, how that will affect decisions we have to make. So he just shares and he will share everything that's on his mind so that we all have visibility into what's, you know, really either driving the company or affecting us externally or internally or whatnot. And then we can sort of go off and do what we will with that information. But it sets a great tone, not just for our discussions, but it sort of infuses the organization with the sort of transparency necessary to enable individual employees to do their business with recognition of what really does matter to the company and what's really going to drive us forward.
Sterling: So I just want to underscore and synthesize what I heard and what I think is so profound here, which is that you all don't just work, you think a lot about how you're working, how meetings are going to be run, the tenor and pace with which you're going to get together over the course of a year. And I'm going to, I'm going to go a little bit off script because I find this just really compelling.
Josh, I wanted to go back to you and ask, is this something that you learned throughout the course of your career or were there moments where you said, gosh, I'm a CEO and we're just working and I want us to be more strategic about how we work. Can you talk a little bit more about that?
Silverman: Yeah, I guess. First I'd say I don't think I'm especially good at it. And so I partner with people who are a lot better than me at it. And so there's someone named Sophia, you know, Tony, Sophia and Anne. Ann is somewhere in the room here, and they're a team to really help drive these operating rhythms. And I, I need help. So I will ask them, what are we not doing well as a team? How are we not spending our time?
I do think time is incredibly precious and I've definitely learned over time to be very thoughtful about how my calendar is used. And so, for example, naming the purpose of a meeting, I think meetings can really only have, well only usually they're either invention meetings where you're trying to create, they're decision making meetings or their accountability meetings, and you structure those meetings very differently and you name it before coming into the meeting, what, what's the, what's the, it's very expensive to get six or 200 people together. What are we hoping to get out of this meeting? And so being sort of very intentional about different types of meetings, how you structure those meetings, I think is really important.
And then, you know, working with people that are way better than me at defining these. I mean, the other thing is just like, I'm also, I think, pretty bad at knowing how things are going on the team because people don't want to tell me. And, and I don't mean that in a bad way actually, I mean that in often a good way. Like you don't want to bring all your dirty laundry to the boss and you shouldn't, frankly, most of the time, like, I like the team to work it out themselves most of the time and let's come to me when it, you know is important. And so I respect and admire the fact that the team is largely trying to work things out, but I do need feedback on where I can be helpful and when I can be helpful.
And so again, having those trusted relationships with people who are closer to what's going on and can tell me, Hey, this is where we're getting stuck. It's been three weeks in a row and we're not aligned and maybe we often aren't aligned in this particular area, which means we need to think about our process or ownership, or there needs to be a more structural fix to why we keep getting stuck. It's just about, it's just about partnership in those areas.
Sterling: Wow. Great. So this word hasn't been said much explicitly so far, but now we'll, we'll make it a little bit more explicit, although I think we've been having a conversation about it anyway, which is culture and how you as leaders are role modeling the culture for the organization, how you're the culture, and maybe even sometimes course correcting the culture. Can you talk a little bit more about that?
Thompson: Well, I'll start a little bit by talking about, you know, that there's sort of the textbook way that you start. If someone says, you know, how to create a culture, you start with values. And I think values can easily be created and then dropped and forgotten. So I think you have to build a discipline around keeping principles, we call them Guiding Principles at Etsy, alive. And I do think that that work that was put into creating those principles and the things that we have in place to keep them top of mind, you know, employees can send each other awards around guiding principles. We talk about them at our all company events there in performance reviews.
You know, we try to keep them top of mind. I do think that that has shaped our culture quite a bit.
And there are things like committing to your craft, digging deeper. Those are performance based. There's also things like embracing differences, leading with optimism, minimizing waste. I do think those five values really do describe our culture in many ways. So I think that is really the start. How do you, how do you have intention around the type of culture you want to create, but then keep them top of mind and put them into the practice of the organization.
Silverman: The say-do ratio is so important, right? What you say is the words on the wall. You go to any company and they're going to have an articulated set of values that are words on the wall
and fine, there's words on the wall. People are looking at Leadership & Strategy for how do you act in stressful, difficult times? And your culture is defined by the decisions you make, the tough decisions you make in tough times. There's someone who's really amazing at their job and they're an incredible software engineer and they're 10 times more productive than anyone else, and they're a total jerk and they treat their colleagues badly. Do you promote that person? Do you allow them to stay? Or do you fire that person? Coach them, if he's that productive, or not? Depending on the level of, how unproductive they're for the rest of the team. 'cause no matter how productive they are, if they make nine other people or 20 other people unproductive or uncomfortable, then you know, maybe not. And how coachable is it?
I don't want to get too deep in that. Look, we had to do a layoff recently. That's tough. How do you lead through that? How do you gain followership? How do you gain trust in those moments?
People are looking at us and we've got to show up. They deserve to hold us accountable to how we show up and how f we show up in these moments is a bigger part of our culture than the words we, we write on a wall.
Sterling: So I want to stay on the topic of culture, but now pivot, and think about how your culture affects the nearly 2 million sellers that you have on Etsy's platform. And I'll just say, and Josh, I was sharing this a bit with you prior to the start of our conversation that moving from California, I've had a lot of fun decorating my Manhattan apartment with Etsy sellers' goods. I mean, they're just gorgeous. And one of the things that I've found so striking is that I've had many conversations with Etsy sellers and they are one, all kind two, incredibly helpful, Three, sincere. I mean, I just think how in the world are you all doing this? Right? Everybody has a bad day. And yet that has consistently been my experience with sellers on your platform. And so how does that happen culturally?
Silverman: First, thank you for supporting our sellers. They're fantastic.And, and I do think we are trying to build a community that is an alternative to Amazon, and Temu, and others. And there are places you can get things that are really cheap and will arrive really fast, but don't have any story, don't have any humanity, don't have any human connection to them. And the core of Etsy is the human connection that happens when you buy something from someone who made it themselves just for you. The story that comes with that, the friendship that comes with that.
And I think that's really, we think that's really important.
And in a world where so many things feel so out of control and maybe we don't feel like we have much agency in them, this is a place I think we as a team feel like we can have agency. Our sellers come from every part of the country and every part of the world and every political stripe, but I think ultimately what all of us share is we want human connection. We want to feel a sense of community. I mean these sellers, they want to feel like they're of service. They're so delighted that someone else loves their product and craft enough to pay them money for it. We need to do a good enough job to deserve serving them, you know? And it's important that we get into the details, you know, and like do the work and are prepared. 'cause their stakes are high.
There's 6 million sellers who count on us to bring our A-game every single day. And that's a big responsibility. And part of that responsibility, by the way, is like, it's pretty easy when you're a leader, as you all soon will be, you know, in an organization you tend to have empathy for the people who are closest to you, right? The people who report directly to you, your teammates.
And we need that. And I think at Etsy we have a fair amount of empathy, but the truth is, there are stakeholders far beyond the few people lucky enough to work at Etsy who really need our empathy and making sure that every person on the team deserves the job, is doing the job well, so that we are serving the customers who depend on us. You know, we need to think about our empathy more broadly than just the people that we, you know, happen to work closest