Jessica Kleiman on Her Time at Peloton and How to Manage Career Incline Rides

Mixing Board Studio Session

Mixing Board Member Jessica Kleiman was most recently the Senior Vice President of Global Communications at Peloton, where she oversaw the brand’s public relations, corporate communications, internal communications and social media initiatives. Before Peloton, she led consumer communications at Instagram and spen over a decade at Hearst Magazines, where she drove PR efforts for 20 U.S. media brands. In the dot com days, Jessica led comms for The Knot, the OG internet wedding planning company.

In this Studio Session, Jessica and Mixing Board founder Sean Garrett talk about leaning into discomfort, staying connected to others in non-transactional ways and career transitions. They talk about Jessica’s time at Peloton and, yes, they go there on holiday ad-gate and And Just Like That.

SG: Tell us about your path. You worked for an internet company during the dot com era and then spent a long time at Hearst. Fast forward, you’re in deep at Instagram and then moved into the fitness world with Peloton. What’s the interconnection between those big leaps?

JK: There is a thread throughout my entire career, and that thread is content.

In the nineties, I ended up working in the media relations department at Capitol Records. I knew that industry wasn’t where I wanted to be. I was doing freelance writing on the side and for one of my freelance articles I interviewed the editor-in-chief and co-founder of the TheKnot.com, They turned around and offered me a job as their in-house Head of PR. So I was part of internet 1.0, worked like a crazy person, a million hours. Took them public. It was sort of this whirlwind heyday that I got thrown into, but it was a great experience.

Then Hearst came calling and I wasn’t so sure. Hearst was seen as traditional, big, private, and old school. But I have this philosophy that you should always be open to having a conversation, because you never know where it’s going to lead you. If nothing else, it’s a learning experience. I’d never worked at a big company. When you think about your career, where are the gaps and how do you fill those? So I took the job, never expecting to stay there for 12 years, which was the bulk of my career. The reason I stayed there so long was that it enabled me to be entrepreneurial. Even though it looks kind of like a traditional company from the outside, it’s very diversified. I got to work on startups, build brands, both digital and print. I got to work on brand development, international, and exec comms. I got my hands into a lot of different things. I had a ton of flexibility and autonomy, and I was able to build a team.

There came a point when they brought in someone new to run the company. And, while he was a fantastic leader, he operated differently in terms of comms. That’s when I started thinking about my next move.

SG: A lot of people would say, “Hey, I’m going to make the best of this. I’m going to stick it out.” But you immediately sensed that this exec wasn’t right for you. To proactively decide to make a move is hard for people. A lot of people would struggle to make this leap when they’ve been so comfortable for so long.

JK: Comfort is such a great word, because that is often why people stay in roles for much longer than they should. There’s safety.People don’t love change. Most people don’t because it’s the unknown.

Someone said to me once, “When you max out on learning at a place, it’s time to leave.” If you feel like you’re just calling it in and you’re not excited to come to work every day anymore or you’re starting to question your value or where you fit into that world, then it’s time to explore what’s next. I stayed two years under this new leader. We had a good relationship and I could’ve stayed longer. But I didn’t feel like I was bringing my A-game. I felt like the floor had shifted a bit beneath me, and that was uncomfortable. And I really trust my gut a lot. Throughout my life, it’s led me mostly to good decisions.

But you also have to lean into the discomfort. I was able to take the time to reconnect with people and to get myself out there again. For PR and comms people, a lot of our job is connecting with others — the media, industry folks, event/conference organizers, you name it. We’re so busy doing that that we often forget in a day-to-day role to actually take a beat and connect with people when we don’t need something. You have to keep those relationships going and, when you get the opportunity, jumpstart them again. I was so heads down in this job that I wasn’t doing enough of that. I realized that I needed to start talking to people outside of my little universe again.

Once I began doing that, it took probably six-plus months to find my way to Instagram.

SG: What was the big takeaway from Instagram that you had? Obviously super different than the traditional publishing media world. What were the themes that carried through even at a place like Instagram?

JK: Yes to being different, but also being similar. The role was a more narrow scope than I had had at other companies. It was specifically focused on all of Instagram’s consumer verticals — music, entertainment, sports, news, fashion, and teens. Also social impact and community was a small piece of it. Those were all things that I had worked on over the course of my career in magazines, and I also saw Instagram as a content-driven company. The content was created by the community and the creators versus editors. But it was sort of like the new magazine. People went onto Instagram and followed their favorite accounts in travel or food or celebrities, and that filled a little bit of that role.

SG: You mentioned that you took a more defined role. But you had been running things, you’d been given all these responsibilities, and now you’ve taken a more narrow role at a place like Instagram. What’s your advice on taking a more narrow role in the career journey?

JK: My goal was to get out of print media and get back into tech. And I wanted to work for a brand that I was passionate about, somewhere I felt like I could bring value because of experience, and a place that I could learn. I hadn’t worked at a big tech company before. And when I got there, it was so Valley-centric and tech-centric, and they didn’t put a consumer lens on comms for a product that is completely consumer facing. We would announce a new feature and my colleagues would be like, “Okay, we’re going to do an exclusive in TechCrunch.” And I said, “Wait a minute. What about Good Morning America? Don’t you want to reach the people who would actually use Instagram Stories?” You want to reach the consumers who are on the platform. TechCrunch didn’t seem as critical to me for something like that. We weren’t raising money. It was a little bit of a battle at first while I tried to educate my colleagues. They came around to the importance of building out an integrated plan and working together, so maybe you gave an exclusive to tech, but you also gave an exclusive to a consumer outlet.

The global piece of it was also a really incredible learning experience, which I took with me to Peloton, where I built the global team from scratch. I learned that some of the best ideas come from smaller markets and markets outside the U.S. They have smaller teams and are able to be a little bit more nimble. They have to wear more hats but they can be under the radar and experimental. I always encouraged my team to borrow from our international colleagues.

SG: What was it like when you first walked in the door at Peloton?

JK: Instagram, in many ways, was my dream job, so I wasn’t thinking about leaving. But I was intrigued by the fact that Peloton had created something disruptive that lived at the intersection of media, technology and fitness, all things I was interested in and had experience in. It was pre-IPO and they had no comms function. It would be going back to building, which I had done a couple of times previously. I knew that I could do it and I liked it. I also just saw so many stories that hadn’t been told about the brand.

Peloton is a media company and a content company as much as it’s a hardware or software company or a fitness company. It’s a streaming media platform where they have talent who have daily interactive live television shows. They just happen to be through a screen on a bike and a treadmill. That was appealing to me. They were under-leveraging that part of their story. When I came in, I was a team of one for the first six months. They were a pretty hot startup at the time, so they were getting press. The challenge was that there was no strategy. They were saying yes to everything from CNBC to a fan podcast. I told the founder and then CEO, “If you’re everywhere, you’re nowhere. You have to start being more selective.” But that’s the kind of guy he was — he just was a super outgoing, friendly guy and wanted to tout his vision. But we needed to be more thoughtful and strategic with how we were doing comms. That’s what I was able to do and then kind of slowly built a team to help support the business goals.

SG: Most people reading this will know the arc of Peloton. My perspective, from the outside, was that it was super hot and you had incredible community growth. The community ended up being this really huge superpower for Peloton. Covid and the IPO happens, so it’s an even faster acceleration. It’s one of these arcs that just kept on going up and up until it stopped going up. And as soon as it was going down, it couldn’t stop going down. A lot of internet companies, technology companies, and other businesses faced this Covid whiplash. An outside force suddenly propelled them and then snapped back as things were coming back. But what did that feel like on the inside? Was it slow and steady or did it feel like you had a sense of vertigo some days?

JK: Many, many days. It’s something I’ve spent a lot of time thinking about, particularly now that I have a little distance from it. After I started and before we went public, I said to John Foley, the co-founder, “The honeymoon’s going to be over at some point. It’s just always what happens. It probably will be after we go public, but I just want to prepare you for that.” I don’t think that’s any sort of prophetic statement, but I was right. When a brand becomes culturally relevant, which Peloton did, it also becomes a target of more scrutiny and attention. And, with Peloton in particular, I have a theory that there are believers and non-believers and not a lot of in-between.

There was a skit that Jimmy Kimmel did at some point that was called Teloton, where the people who couldn’t shut up about their Peloton bikes had a hotline to call because their friends and family were so irritated hearing about it that instead they could call this 1–800 number and talk about their Peloton. By the end of the skit, the person on the hotline wants to shoot themselves, basically. It was hilarious, and there was resonance to it because the people who were in it, they’re obsessed with it. And then there are people who are like, “I don’t get it. It’s a stationary bike.”

And, honestly, I didn’t really get it at first either. It was during the interview process where I actually requested to meet with the Chief Content Officer at the time and VP of Fitness Programming, Robin Arzón. Because I saw it as a media company and I really wanted to meet with the person who owned content programming. I was out in Palo Alto and they had a big sign in the lobby of my hotel that said, “We have Peloton bikes in the gym”. I thought, “I’ll take a ride with Robin to see what it’s like before I meet with her next week.” And I got it right away. A light bulb went off.

In the world we’re living in now, where everything’s clickbait because of the media landscape changing, for one, and based on algorithms and click-throughs, Peloton gets clicks. And if Business Insider or CNBC posts a piece with Peloton in the headline, that’s because they know people will click on it. The lovers will click on it and the haters will click on it. It creates, for lack of a better word, this flywheel where it just doesn’t stop. You have to remind yourself, your team, and your executives that, when people stop talking about you, that’s when it’s time to worry. Because as long as they’re talking about you, you are culturally relevant.

There were a lot of hard days. I’ve dealt with a lot of crises over the course of my career, but not at the pace of Peloton. And it’s a fitness company. I couldn’t understand. It wasn’t like the Exxon Valdez crisis. It was stupid crap that was getting major headlines, and it was relentless. Like “holiday ad-gate”, as I dubbed it internally. The Sex and the City situation. These are things that, on their face, don’t seem like such big news stories, but they became really big news stories. The relentlessness of that was hard to take. And it makes it difficult to be proactive on all the other things, because you’re just literally playing Whack-a-Mole.

SG: So this holiday ad comes out and you start seeing the reactions to it. We can talk about the strategy on how to react to it, but here’s the human side of it, which is like, holy shit, we have to deal with this thing, but we’re a team and we’re going to do it together. What’s the conversation that you have with your team to make people feel like, hey, we got this, we’re going to get through this together. Because that’s what you remember, those moments as a team. You remember the shit, but you also remember that togetherness. How did you manage the human element to situations like that?

JK: I think the best way to keep your team motivated and connected in tough moments is to be as honest and communicative as possible. I often kept the majority of my team shielded from being in the trenches on crisis situations so they could focus on being proactive on all the other news we had to share, but I would always try to update them in real time on how a situation was unfolding, how we were approaching it from a comms perspective, how they should handle questions about it, and what we had learned from the crisis or challenge. This helped keep them updated, feeling connected to the “action” and privy to what worked and what didn’t along the way.

If I look at the holiday ad-gate situation versus the Sex and the City situation and how we reacted, it was very much because the team was a lot more cohesive when the Sex and the City thing happened. In the original structure, comms was pulled out from under marketing and it was made its own function. Social fell under member experience. So marketing, social, and comms were three separate functions and the communication and the collaboration wasn’t as good as it could have been. And those things never come more to the fore than when crises happen.

At that point, I had no involvement in any of the advertising or marketing, I didn’t see storyboards or scripts or anything. I just saw the finished product. And, at the time, I remember they showed it at an All Hands before it started running and people were excited that we finally were showing some sort of member journey versus just someone sweating on a bike. Because it had been very performance driven to that point. Once the ad started running, it was actually doing really well. We were running two holiday ads at the time and this one was over-indexing so much that they started to run it a lot more than the other ad. Over Thanksgiving weekend, when everybody’s home and watching football and has the TV on, the ad was just running constantly.

There had been some complaints and some negative comments on YouTube, which was managed by social or community. And they turned off comments. So when people can’t comment on YouTube, guess where they go? Your old stomping ground of Twitter, which is where all the journalists go. There were things we could have done to prevent this from even turning into what it turned into. At the beginning, if you remember, it was sort of a joke. People were making fun of it. There were memes of the guy from Get Out next to the Peloton wife. And I didn’t want to be reactive. I thought this would be a 24 to 48 hour thing, and that’s that. I woke up on day two or three and it had jumped the pond and had started getting press in the UK. The head of our agency there pinged me and I remember thinking, “We’re gonna have to say something.”

We put out a statement, but the powers that be didn’t want to pull the ad. Hindsight’s 20/20. It’s like, should we have pulled the ad? I’m still not sure, as that would have fed right into cancel culture. And what started out as making fun of the acting evolved into this very negative sentiment. Especially on social media, which makes things move much more quickly. Then Covid happened and people looked back and said, “Oh, now we all wish we were the Peloton wife because we can’t get our bike.”

SG: So now you have a combined team or more harmony on the team. How did you make that kind of harmonization happen? Was it because of the bad stuff that happened, or was it just a natural evolution? What helped lead you out of silos to the place of integration?

JK: You learn more from failure than success. A few things happened after ad-gate. We thought, “Okay, these are things that we should connect the dots internally on better next time. There were probably signs we could see.” After ad-gate, my VP and I would get the scripts for review. But frankly, over that next couple of years, our former Head of Marketing left. The President, to whom I had reported, decided he had too many direct reports and restructured the company. We had scaled very quickly. He moved comms and social and editorial under marketing, and we had a new Head of Marketing who really gave us a seat at the table because we were all part of the same function. So now, social and editorial was under me, and I was rolling up to the Head of Marketing. We were much more cohesive, much more integrated.

SG: So then And Just Like That happens. What was the difference?

JK: There was another situation that happened, also on Twitter, before ad-gate. This guy Clue Heywood who did this whole thread on Twitter with just images of people in really ridiculously fancy houses riding their Peloton. It wasn’t funny for us at the time, but it was very funny. The Head of Social, who didn’t report to me back then, and I were like, “Let’s clap back. Let’s start posting pictures of Queen Elizabeth in her office with a Peloton bike in the background or the Hall of Mirrors at Versailles with bikes in the background just to show that we’re in on the joke.” Right? But marketing was separate. And I remember our Head of Marketing was out that day. Our Head of the Member Experience was out that day. So we ran it by legal and they were like, “Copyright issue.” We didn’t have the autonomy or the decision making power to just move forward with it. We missed an opportunity, and it really killed us.

And who got the last laugh after ad-gate? Ryan Reynolds. He cast the Peloton wife in his Aviation Gin ad. It was brilliant. We were kicking ourselves a little bit like, “Why didn’t we do something like that?” When the Sex and the City situation came around, we were a much more well-oiled machine. We had already been speaking to him and his team about doing something together, and so we pivoted very quickly and said, “No, no, no. This is our moment.”

And, by the grace of God, we pulled it together. We were able to get Chris Noth on board and move Jess King, our cycling instructor, around so she could do the shoot. We secured a location. We flew in Ryan’s team. Everyone was rolling up their sleeves. We were able to make it happen in the course of a weekend, which was incredible, and something I’m really proud to have been part of. We finally were able to laugh at ourselves a little bit and be in on the joke and have a personality. We took ourselves too seriously in our brand marketing for a very long time, and it didn’t match up with the personality of the brand, once you were in it. There was a disconnect. That’s moved closer over the past year or two. But it took a long time and a lot of teamwork.

SG: If you work for a company like Instagram or Facebook, connection becomes a buzzword. I think people view connection in this transactional social media form now, which is unfortunate, because the word, and what it actually means, is very powerful. The things you were able to pull off at the end — shifting from overly serious to being able to laugh at yourself — that comes out of strategy, but it also comes out of just being allowed to have real conversations with people. Maybe not all those people are in marketing or in comms, they’re across the board. Tell me about the intersection between actual real human connection at work, actually getting stuff done, and making it come to life.

JK: Another catchphrase that’s overused these days is community. However, if you look at Peloton and Instagram, those are two brands that are particularly driven by community. It works really well and that connectedness is critical to the success of both of those businesses. One of the reasons that Peloton flew to such heights during Covid was because it helped people replicate the connection that they felt when they went to the gym or a boutique fitness class. They could do it from home where they were sequestered during Covid and they could connect with an instructor who might actually shout out their leaderboard name. People really crave that connection.

One of the biggest challenges during Covid was connecting with our colleagues when we weren’t in the same physical space as them. What you missed, and still miss, because people aren’t fully back yet, are those organic hallway conversations, those spontaneous brainstorm sessions. Now you have to set up a Zoom and it has to be more formal. When I was a team of one, I managed to get an intern for that summer, pre-Covid. And I remember I would notice her craning her ear to listen because we all sat in an open office plan, she just was a sponge. Through osmosis, she was learning. That sort of went away during Covid, which is really sad, especially for people starting out in their careers during this period.

But it helped level the playing field, where suddenly the person who was based in Berlin or London or Toronto saw as much of everyone as the people who used to sit together in New York did. We tried to find ways to connect on a human level during Covid — we had a Slack where we’d randomly assign you to a colleague and you just spend 30 minutes on the phone talking about non-work stuff. It really helped. It helped forge those relationships and connections you would get by being together. People talk about, “Oh, you always want to be networking.” But I don’t like that word because it has “work” in it, and it really shouldn’t feel like work. Connection is really a freer thing. It shouldn’t feel like a transaction. It’s relationship building, and our field is a relationship business. You are only as good as your relationships. That’s your currency. It’s as important to work as hard on that as you would on your writing skills, strategic planning, or anything like that.

SG: At least for now, you are consulting and checking out that world. As you reflect and think about what’s coming next, what career advice do you give folks who are like, “Wow, I would love to work at Instagram or Peloton. That’s incredible. How would I ever have a career like that?” If someone was lucky enough to get on a call with you and ask your advice, what would you tell them?

JK: If I had thought, when I graduated from college, or even 10 years after that, that I would work at Instagram or Peloton, it wouldn’t have been possible because they didn’t exist. Even now, in my post-Peloton journey, it’s less so for me about “I want to work at this brand”. Because sometimes a brand can seem great and, then when you get inside, it’s actually not as great as you thought. So what is it that excites you? What are the non-negotiables for you and can you find those things in a particular job?

If you really are focused on working at a certain place, it’s so much easier now with social media to connect with people. When I started, there was nothing. I found my first job because I went to Barnes & Noble and I looked in an internship book and I copied down the contact information for PR firms that represented media brands. I sent letters to them. This is how ancient I am [laughs]. But I did it. And I just put in a little extra elbow grease. Now you can go on LinkedIn and see who you know, or who is in your network, that works at Instagram and then try to connect with them. People are busy, but if you try 10 people, maybe one or two will be willing to spend 15 minutes with you and then you’ll be top of mind. It’s putting yourself out there. People can’t be afraid to do that. And putting yourself out there when you don’t necessarily need something immediately from people.

SG: What about people who are in big jobs and they’re wondering, well, should I be looking? Should I be doing anything? You posted recently about how you should always be looking for your next thing or always be in the consideration for it. Explain that.

JK: I wrote a Medium post about this and somebody in the comments said, “Well, I don’t think you should always be looking for a new job.” And I actually agree, you shouldn’t always be looking. But to your point, you should always be open, right? It’s not so much about actively looking. Because I’ll be honest: I hadn’t dusted off my resumé in years. But you just never know when something is going to cross your transom. You also never know when the tides are going to change in the job you’re in. Looking back now on my career at Peloton, I really drank the Kool-Aid. And I still do as a member and as a believer in the brand and what they’re building. I don’t think I would’ve necessarily left for a long time, but things change and shift. I look back now and I think of the gift that I’m able to move on to the next phase of my career. And I feel for a lot of the people who are still there and are kind of like, “What do I do next?” And don’t have the time or the breathing space to think through that because they’re in the mire.

It goes back to the idea of connection. If you have blinders on and you’re only focused on doing your work, talking to the people who also work at your company, and going home at night and doing whatever you do — just make small goals. Once a week, I’m going to reach out to someone who works in my industry or a recruiter or whomever, someone who works at a company that I admire and try to make a contact. That’s only one person a week. Everybody can do that. You have to take baby steps and then be patient too, because these things take time. Look at my Instagram journey. That took maybe eight months or so to get that job from that first conversation to my start date. I wanted the job, so I hung in there and it came to fruition. But you just have to be patient.

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