Navigating Leadership During a Global Pandemic and a House Burning Down

Jenn Clevenger, VP of Engineering, Etsy

With their position and responsibility, it’s easy to forget that leaders also go through hard times just like the rest of us. One of the things I really enjoy about Jenn Clevenger, VP of Engineering at Etsy is how much she embraces her humanity, inviting all of us to embrace our own. During our conversation we talked about how she finds balance in the midst of uncertainty, how she keeps perspective and how she thinks about leading others through difficult times.

It's so good to see you, neighbor.

Hi, neighbor. Nice to see you too.

We met at the LeadDev New York Meetup where we both spoke. We were talking about living in Brooklyn. I asked where you lived. We literally live two blocks away from each other, maybe three blocks away.

On the same street. What are the chances? Brooklyn is huge. 

We'll actually get into why we're neighbors today. But first, can you give a quick introduction of yourself to folks who did not meet you at the New York LeadDev Meetup?

Yes. I'm Jenn Clevenger. I am a Canadian living in America. I came here, oh god, it's probably about 18 to 20 years ago now. I currently work at Etsy. I'm a VP of engineering. I run data enablement, so that's all of data engineering plus experimentation and science, and I'm super happy to be here.

I heard your little "about" accent, and I love it. I'm from Detroit and I've worked for two Canadian companies. I used to say "eh" a lot. People ask, "Are you Canadian?" I'm like, "No. I grew up a half hour from the border," so I love Canadians.

Every once in a while, it comes out. I don't think I say "eh" as much as people would like me to, and I don't hear my accent. But every once in a while when I'm talking to someone, they'll stop me. If I meet someone new, they will stop me and be like, "Are you Canadian?"

We're not here to talk about accents, although I think it's always fascinating. Can you share a little bit just for context about your path into leadership?

Yeah. So probably similar to a lot of people, my path was very zigzaggy. I was not one of those people that visualized what I wanted to be when I grew up and then took a straight line there. I kind of meandered my way here.

I started my career writing trading software inside a bank. I went to a school that had an internship program, so I worked every four months and I went to school for four months and I did that for five years. My last internship was at Morgan Stanley in New York. So I got hired, and I came back. And so that's how I started my career.

I've always really loved writing code because it's very logical. It makes a lot of sense. One of the things that I disliked that I discovered in this job, is I could come to work, sit at my desk, put my headphones on and not talk to anyone at all. I'd be doing an aces job, an amazing job, just writing code all day.

I missed the people part. There was no part of my job that really required me to talk to people or care about people or do any of those things. Back then, we didn't have PMs. There's no designer, there's no one to talk to except for the traders, the people that you were writing the software for. So I ended up going into consulting at PWC and working in Forensic Data Analytics and Technology, which is interesting and I really liked it. While I was there, I got married, I got pregnant, and I had our first kid. Being in consulting is really, really hard when you have a kid, especially in forensics because it's very reactive. If someone has a security breach, we assemble a team and go over and figure it out, and pull all-nighters for the next four days to figure out what to do.

So I needed to find something different for the new “married-with-a-kid” stage of my life. I had started as an associate there, like an analyst on the tech side. And then I moved my way into management. So I would say this was the beginning of my management journey. However, we were managers of work, not people of engagements, not human people.

Stop me if the story is getting too long and boring.

No, it's great.

I'm tracing my path. (laughs) The next part actually gets interesting, I promise. So I wanted to get back closer to tech - I felt like I had gotten too far away from writing software and doing the things that I love. But I was in analytics and on top of that and my resume was very corporate-bank looking. So I found that it was really hard for some of the tech companies that weren’t banks to look at my resume and be like, "Yeah, this is a person who I could see working here."

If my resume had a picture, it'd be me with a little pencil skirt and my button-up shirt, my business casual going to my corporate office full of cubicles. And so it was really, really hard to get potential employers to see me outside of that stereotype. I found Etsy because I heard they had a cool culture and a great reputation. I watched a bunch of talks that were so cool, I read the Code As Craft blog. I was like I need to work at this place.

They had a job as a manager of a data analytics team. So I applied for that job and I got an interview, and I went to the interview and I remember when I left that office, I'm not a person that talks to myself. I was like, "I must have this job. I need to work here."

Even just walking in, I'm used to working in a gray cubicle farm. And in the Etsy office, one thing I noticed is they had heating ducts across the ceilings, it was kind of an industrial-type space. Someone had knitted koozies for all of the heating ducts, like colorful koozies. And every room had cute little tchotchkes in it. It was just this amazing place.

And everyone I met was so nice. Anyways… I didn't get that job, I was devastated, but I moved on and I took a job at MetLife. I was like, "I guess this is me. This is my thing." Don’t get me wrong - MetLife is a great company. The people there are lovely. It just wasn't tugging at my heartstrings the same way that Etsy did.

But six months later, someone called me from Etsy. His name is Rafe Colburn, a person who would go on to become a wonderful mentor for me and a fantastic friend. He's like a dear friend now. He called me or emailed me randomly and he was like, "Hey, I don't know if you remember me, but I was on the interview panel for this other job that you applied for and you didn't get it. I have a job opening up on my engineering team, a manager job, and I would love for you to apply for it."

And so long story short, I applied for it. I got it. And I feel like the reason I tell people this story all the time is that you never know where the opportunities are. Sometimes the opportunities are hidden in the things that you think were a failure. Like damn, I'm so upset that I did that or that I put myself out there. Or that conference was a waste of time, or whatever it is. You never know what kind of connections you're going to make that are going to change the course of your life.

It sounds dramatic, but in my zigzaggy career, I feel like these last few events really changed the course of my life and my career.

It's a great philosophy. You never know...

You never know…

Where your life is going to head and where that opportunity is going to come from.

Yes, yes.

And you've been at Etsy now for how long?

Seven years. It's been seven years, a long time.

How big was Etsy when you joined?

We were probably about 800 people but hiring fast. I always joke that if I hadn't joined during that time when Etsy was hiring almost indiscriminately, I would never have made it in the door because my resume was so weird looking. (laughs)

Well, yeah, pattern matching is a whole thing in hiring. But we won’t digress into that topic. So how big is Etsy now?

I think we're probably about 3,000 if you count everyone across all the brands.

What’s the group you lead? 

I lead an org called Data Enablement, which includes Data Engineering and Experimentation Platform and Science. Data Enablement is responsible for making it easy and delightful for anyone to access data internally at Etsy for product development, machine learning, analytics, experimentation, marketing, finance, accounting, etc.

So our customers are internal, but they're literally everyone at the company that wants to touch any data for analysis.

How big is your org?

We are probably about 90 people right now.

There's a lot of talk about the difficulty of leading in the early days of the pandemic, but I think also we don't talk enough about a year in. I'm curious about some of the challenges you faced as a leader a year leading into the pandemic.

I would even stretch that to say “a year plus after the height of the pandemic” – it's still a struggle. 2020 was hard obviously for everyone, for All The Reasons. But I think what people didn't anticipate, and I didn't anticipate either, is what happens after. It turns out there's no runbook for how this is going to play out in the long term. Related to work, I think the job of being a people manager is harder than it ever was.

Everything was hard in 2020 but maybe the adrenaline and the chaos just sailed everyone through. Now the dust is kind of settling and people are expecting some normalcy, but there isn't. We're still not there. Being a manager of people has been difficult because people are having a hard time. As a manager, a huge portion of your job is caring about the humans that report to you. That emotional energy is exhausting when almost every single person is going through something that requires some amount of extra care.

Let me talk through some tangible examples that are useful. Over the pandemic, Etsy grew a lot as a company, as a lot of the e-commerce companies did, so we’re dealing with that company-wide growth. On top of that, Data Engineering was growing a ton as well based on our continued investment in data and machine learning. Data Eng used to be a small close-knit team, and then all of a sudden we grew into this huge thing. I won’t get into all the normal reasons that scaling a team is hard, but now all those things were happening during an incredibly difficult time when people simply have less capacity for nonsense. 

Everyone has a nonsense bucket and normally you have some amount of regular nonsense happening in your life. Usually, you have some capacity to take on additional nonsense here and there… but, over the past year, our nonsense buckets have filled to the top and we're like, “I don't have any space for any more nonsense!” So every tiny little thing makes your cup of nonsense overflow. And it's exhausting. People are tired. People don't have the capacity anymore to deal with it elegantly.

And so I think that is the challenge in front of us. How do we continue to try and push forward and live our lives? Life is life. Something always comes up. How do we create more space in our nonsense bucket?

That's perfect. That's exactly it. Well, so that's all going on. But also your house burned down.

My house burned down.

Which is why we are neighbors now.

Yes.

I remember when you told me how you ended up being my neighbor. I was like, what? I can't imagine losing all your belongings and your home in one fell swoop. You didn’t seem outwardly traumatized by it. Perhaps you had already dealt with it.

How did that impact you as a leader? 

It burned down in April of this year, so it hasn't been that long. You're right. I think I talk about it a little bit casually. I was talking to my sister about it and I think that as a family that has experienced real, sudden unexpected loss, it’s easier to frame my house burning down optimistically. In 2005 when I was 24, my mom was killed in a car accident very suddenly. I still vividly remember the phone call from my Dad. That was a life-changing event. Everything in my life changed from that moment. It just changes your perspective. Sure, my house burned down, but nobody died.

We weren't even home. So all of the things that are terrible about an event like this happening, we didn't have to experience. I have two little kids, we didn't have to flee in the dead of the night from a burning smoking building and then sit on the sidewalk and watch it burn down. It was like 4:30 in the morning. We weren't even there for any of it.

So I just feel lucky - yeah, this is a thing that happened. It's not awesome. It sucks, but we didn't lose anything that is going to change my life. It is an enormous amount of work. It's going to take a year or two to build the house back, and it's super inconvenient. I'm in a rental for who knows how long, and we don't have that many things anymore. 

I just added (rebuilding after my house burned down) as a track of work to the tracks of work that I'm managing. It’s just one more thing that I'm going to do and make space for, for the next year. It's temporary. It's a great opportunity to practice my prioritization techniques and cut out the things that don't matter.

Yeah, there's some clarity in that. There is something about when you deal with death in a close sort of way, younger in life. I almost died when I was in my 20s.

I saw that. I read that in one of your interviews. I was like, "Holy cow, this is crazy."

Yeah, I flatlined. I mean, you know you're dying. When your mom dies so tragically, I think it probably changes your perspective and it gives you, I hate the word resilience, but it gives you something, a perspective maybe that changes the way you see things. 

Yeah. I agree. The super cliché, what doesn't kill you makes you stronger, it's a real thing. People say that for a reason. It's true. I think you learn from those things. It shapes you.

It does. How did you stay balanced in the midst of all of that? Were you affected? Did you get close to burnout? Did you feel any of those impacts as a leader?

I mean, it's exhausting for sure.

What was hardest about it? 

Remembering to be kind to myself and give myself a break. This continues to be hard. I'm super ambitious. I fancy myself a hard worker. I always want to do my best everywhere. That matters a lot to me. 

It took me a really long time to get to a point where giving myself a break felt like an okay thing to do publicly. To say - I'm going to step away because  I'm not my best self right now, or I need some time to do nothing or whatever.

I learned the importance of stepping away working at Etsy because that's the culture there. It's been really, and I see other people do it and it allows me to do it. Even if it’s against my nature I know when I do it, it allows other people to do it. As a leader, this is a great opportunity for me to live those values in front of people as an example.

If I turned this into advice for myself that I would write down on a little sticky note and look at every day, it would be “Work hard when I have the energy for it because that gives me joy. But when I don't have it in me, then do myself a kindness and just lean out for a bit instead of just pushing on when it's not energizing anymore.”

I stay balanced through vicious prioritization plus staying tuned in with myself and continuing to myself, "Lean out, it's okay." 

I think it is too. Especially because when you're in a leadership role, the sense of responsibility that you feel for the people and the org to move these things forward is tremendous. It can make it very easy to prioritize everything else above our own particular needs. Sometimes, I think leaders even feel selfish. (for taking care of themselves)

Yeah. Everything else and everyone else, I think, is the thing that makes it hard. It'd be different if I was like the manager of a bunch of boxes, but these are humans that I'm talking about. It matters if I engage with the problems of the day-to-day. It matters if I'm trying to think a couple of months ahead so that when they get there, everything's not going to crumble down. All of those things matter to people.

Especially these days, like I said before, people’s nonsense buckets are full. So the wiggle room to not take care of things for people, I feel like is low. But I do think it's important to give yourself a break.

I also like what you said too about doing it publicly, not just sneak away like, "I'm still here. I'm tippy tapping."

Yes. Just be like, "Hey, I'm taking the day." Recently, I've been taking a lot of meetings with contractors because we need to get a contractor signed so we can start the rebuild on the house. I was just telling you before this call, that's the thing that's been stressing me out - that we haven't started yet. It's been six or seven months. Everything in New York takes forever, and everything these days takes forever. The supply chain is awful. Everyone's like, "Oh this is a terrible time for your house to have burned down." I'm like, "Oh, thank you for your input."

I'm sorry I didn't schedule that appropriately. (laughs sarcastically)

Right. (laughs) This wasn't what I wanted, it wasn’t planned! So I've been doing a lot of meetings with contractors. This is not part of my job, but we've been going looking at their sites and meeting with them and sitting down and it's an important choice. And I've been taking the time to do that and I just try to do it unapologetically. I got to do this thing.

It's like modeling being a human and being a human and a leader, but being a human.

Yeah, and having things outside of work and it's okay.

That's an important message. I know I felt it too. I sometimes felt a twinge of guilt, like if I knew there was something sort of not a roasting fire but an ember and I wasn't dealing with it. And I was like, I had to get over that guilt sometimes. 

I say that all the time to people when they ask for advice as their careers are going through the management track. What kind of advice can you give me? One of the things that I learned this year is that exact analogy about the embers. As your org grows and you look around, the scope is wide and broad enough that there are always going to be a few little embers.

As long as you know where they are and they haven't burst into fire yet, you can take care of them one at a time. Start with the biggest fire, and go and help to make that better. Communicate about what you’re prioritizing, like "Hey, I know that there are a few things that aren’t perfect right now, and I can’t focus on them quite yet, but I promise I will get to them," Don’t do more. Just be transparent about what you CAN do. I think that honesty, transparency and human approach really helps.

Love that. All right. It's great advice. So you are also recently promoted to VP of engineering. Congratulations.

Thank you.

How was that being promoted in the midst of everything going on? Did it feel like more pressure or not at all? Was it just like, "Yes, I'm so excited, I'm prepared for this. I've been wanting this"?

Yes, it felt like the latter, like so excited for this, so prepared for this. But in the context that everyone knew my house had burned down. So I think people were aware of the size of my bucket. My capacity, my emotional and professional capacity. My house burned down right around promotion season. I went to my boss and I said, "Hey, I know you were going to put me up for promotion. Does this change anything?"

He was like, "What? No, your promotion is a recognition of your entire body of work and everything that you've done. And it’s a statement about your potential for the future and how we believe that this is a great path for you. And this “house burned down” thing is just an event that happened. It's a finite tiny event in the grand scheme of things, so like why on earth would it make a difference?" And I love that.

This is the second time that someone at Etsy said that to me about a life-changing event because the first time was when Rafe called me and asked me if I wanted to apply for this job. I was pregnant at the time and I showed the email to my husband. I was like, "Oh my god, Etsy's not going to want to hire me right before I pop this baby out." The timing would've been such that I’d work for a month and then go out on parental leave, which Etsy gives 6 months for.

I told Rafe I was pregnant when I thought we were far enough along in our interview. I know it's illegal to discriminate against pregnant people, but women know this is still something to worry about. Companies find a way to do it. It's sad, but it's true. I hear those stories all the time. (We both nod.)

Rafe was like, "Oh, that doesn't matter in the slightest. If we hire you, this is a long-term investment. It’s us saying we think that you're going to be awesome here and we really want to partner with you. You’ll have a wonderful and long career here and your pregnancy is just a tiny little piece of that. And also it's a totally normal life event. Why would we care? Congratulations!" 

It seems like Etsy looks at longer time scales. They're not just looking at what you produce today. They're sort of operating on longer time scales when they think about their team and all of that, which is incredible for the culture.

The other thing that’s coming to me is grace for yourself for being human. Etsy very much seems to me that it allows you to be a human, which allows you to be like, okay, yes, I can be a human. It gives you that permission to just be a human.

Yes, a hundred percent. Be your whole self-at-work vibe. I feel like I say that all the time. This is the first time I feel like I can be my whole self at work, all of my strengths plus all of my weaknesses, of which I have many. I'm a person that has tons of imposter syndrome, always staring at my weaknesses, but I don't feel ashamed of them anymore. I think that's huge because then it allows me to work on them shamelessly.

Yes, really living those values. I mean people like, oh, the company values. And yes, there is sometimes a disconnect between the values that we state and the values we live. It seems that Etsy really lives its values.

Yeah, a hundred percent. You're absolutely right. A lot of companies say they have values, which is great because they mean to, and I believe that they want to. But if that doesn't percolate down and permeate every layer of the org where every manager is living those values in representation of the company for every person that reports to them so that everyone feels the freedom to also live those full values, it doesn't work.

Yeah, absolutely. All right. I have one last question. I could talk to you forever.

Same.

What advice would you give other leaders who are facing external headwinds along with personal ones like market stuff? There's always market stuff going on, stuff going on in the world, recessions, whatever. But how about someone who's facing, because you faced both of these at the same time?

Yes. Great question. What advice would I give? I mean maybe it's something as simple as … life is hard and you need to make space for that because you never know. For example, I was reading a bunch of your articles on your leadership conversation series, they're so good. One thing that popped out to me. I was reading the one about leading with a chronic illness.

Dizzy Smith, who has an incurable form of cancer and is a leader.

Yes. Fascinating and such an optimistic story. Life is hard and you need to make space for that. And everyone should do that for each other and allow each other to make space for that because you never know what's going to happen. You just don't.

Work is just one piece of the tapestry of your life, of the quilt of your days, or whatever it is you want to call it. Work is just one piece. 

When I was younger, I thought work was everything. It defined me. The jobs that I've had in the past felt so important at the time and they're just lines on my resume now. But who is always here for me? What do I still have? My friends, my family, my hobbies, things that bring me joy - those are the things that we need to make space for.

Life is hard and you need to make space for that. And that doesn't mean that you only make space when something traumatic happens. It means always making space for it so that when life gets hard, you have a balanced portfolio of things to lean on.

I love that. I think there's a stereotype and perhaps true that work is a leader's life. I mean, look at all those movies where the executive is always on the phone, "I got to go take a call, I got to go to a meeting." Or the exec who flies out to a business meeting at Christmas. I mean those are based on some sense of truth. And what you said to me, what you said was it used to define me early in your career. How did you move? It's so interesting to me that as you get further into leadership, it seems like you move further away from it, defining you rather than more. How did that happen? Was it conscious? 

It is probably a combination of all of the things in my life that have happened. So they're little, if you think of your life as a big barge that's kind of moving in a direction, it's hard to change the direction, but little by little like these little nudges. I would say my mom passing away was one of them. It totally changed my perspective. That was one nudge.

I think joining Etsy, changed everything about how I thought about my job as a manager, which is very different than a leader. I think those two things are very different.

So different.

It seems those nudges along the way helped you redefine yourself. How beautiful as a leader to give that as an example, to be an example of that, because leaders are always examples. No matter what, we want to be role models or examples. We always are because you lead on a stage. And how wonderful that you give that to people by doing it yourself.

Thank you. That's very kind. I still think of myself as the person that I was in my 20s. So it's been an interesting ride and every once in a while, I'll talk to someone who's like, "Oh, you're setting a really great example for people." and I’ll think - "Oh, I am?" Because I feel like I'm still learning and growing so much. So maybe I feel like - that's almost me.

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