Jess Aptman on Building Trust and Staying Curious
Mixing Board Studio Session
Jess is the Chief Communications Officer at Zocdoc, where she’s been for 13 years. There, she leads the Public Relations, Internal Communications, Government Relations and Brand teams. Before that she was at Outcast, focused on consumer tech clients. And in a past life, she spent many years in the agency world representing lifestyle and hospitality brands.
In this Studio Session, Jess and Mixing Board Founder Sean Garrett talk about why the different functions of communications are more effective when they work together, why you shouldn’t manufacture spokespeople from scratch, why we should normalize googling when you don’t have the answer, and why there is rarely just one right answer – instead a series of choices and tradeoffs.
SG: What are you up to now?
JA: I recently hit 13 years at Zocdoc. When I tell people, they’re shocked—and honestly, no one more so than me. But every chapter has been so different that it’s never felt like standing still. Today I oversee Communications, both External and Internal, as well as Government Relations and Brand. It’s a really nice mix of functions that are greater when they're together.
SG: Tell us about the different phases of your time at Zocdoc.
JA: While it has always said Zocdoc on the door, it’s been a few different companies. My scope has also grown a lot—I started with a focus on PR and over time built or inherited Internal Comms, GR, and Brand. The evolution has kept it really interesting.
I’d say it’s been four different Zocdocs since I started. The first one, when I arrived in 2012, was all about getting the word out about this revolutionary ability to book a doctor's appointment online, launching in new markets, adding doctors, adding employees, go, go, go, growth. Then around 2014 into 2015, I call it the ‘uh-oh’ years where unsustainable growth was catching up with us. We had the wrong business model, slowing revenue growth, high burn, and culture problems. It was a tough moment where we had to take a look at ourselves and say, okay, we can't keep going down this path. We had to make leadership changes and intentional culture changes, and find a more sustainable path forward.
That was a precursor to the third chapter, which started in 2017. We had to pull off a pricing model change and turnaround—something very few companies manage once at scale. When we first started exploring this, Adobe and Netflix were the only two companies we could point to who had done it—which wasn’t great. It was daunting. We had to do really hard things—like charging our best customers more, working to change state and federal regulations to unlock the new pricing model, and proactively shaping the public narrative around those changes. Just as we started making headway on the turnaround, we ran right into COVID. It felt like we were constantly fighting our way out of foxholes in those years.
By 2022 into 2023, we had recovered from the COVID disruption, finished the pricing model change, and started to reap the rewards of years of hard work and sheer grit. Today, we're on the other side of the turnaround in a foot-on-the-gas, offense chapter. We have healthy, profitable growth that lets us invest in scaling the business in the right way.
SG: You mentioned that all the functions of comms all work better when they work together. I agree. Tell us about that.
JA: The functions have different initiatives and outcomes they’re driving toward. But what’s true across all of my teams is that they focus on building and keeping trust, credibility and goodwill with important stakeholders: the press and the public, employees, regulators and legislators, customers and prospective customers.
They are also all high context functions and work best when they've got a broad lens on what’s happening within the company and in the world. I don't treat them as four separate teams, but I approach it with a cohesive mentality. Nearly every article I share has a takeaway for each function. We use our weekly team meeting to share context and connect important dots. GR may flag a policy change for Internal comms that we might get a question about at the all hands. PR may ask about a media effort to advance a GR goal on the hill—or shaping a broader narrative that ladders up to our policy goals. Brand may find a great social UGC piece that Internal comms can share to motivate team members. We try to act as a hub and spoke context center for each other and for the business.
SG: Do people who work on GR or brands say I work on the communications team or do they say I work on the brand team?
JA: We don't really think about it in terms of departments. They would probably say I sit in Comms, but I work on Government Relations or Brand, etc.
SG: That's an awesome outcome and it's very natural to what you've built over those years. It's one of those instances where being there for that amount of time, you're instilling that DNA into the organization. Obviously there are organizations where those four different functions operate in four different silos and you don't have that. I'm curious what you think about how that makes you move differently within the org and be more effective with those specific audiences, having all those different groupings together.
JA: We’re really connected and can leverage so much of one another’s work. To give a recent tactical example, Brand is working to scale how we collect impactful user stories. In our weekly meeting, GR was like, “Oh, we have a whole ‘patient stories’ landing page already built out from a grassroots campaign.”
More strategically, PR and GR collaborated on a response flow chart for hot topics, which informs our Internal comms and Brand postures, too. There’s more overlap in the Venn diagram than it seems. Different stakeholders and tactics, but that overlap allows us to craft cohesive narratives—ones that don’t just tell a story in the press, but are reinforced internally and out in the world.
SG: I assume that not everyone at Zocdoc has worked there for 13 years. I'm sure you've also had people that you've reported to who have left or changed. What does it mean for you to be this consistent piece who's seen it all? What has that meant to you and how's that influenced the impact that you've been able to have?
JA: I'm actually less of a rarity than you might think. There's a pretty large group of people that have been here for 5, 10, 15 plus years. There is something really special about Zocdoc that keeps people here. A ton of people made a choice to stay through the hard times and fight the good fight. While some of our friends left (some of whom later came back, which I love), a bunch of us took the other side of that bet.
It helps that I’ve lived through so many pivotal moments and can be a bit of a historian. But you can’t only be a historian, stuck in the past and looking in the rearview mirror. I view my job now as putting our past in the context of our future. A lot of the lessons we learned in the hard times are core to our DNA now, so it's helpful to tell those stories when they’re useful or instructive.
The context I have and the trust that I've built by helping the company navigate some really difficult, high-stakes moments has been valuable. It has earned me the opportunity to expand my scope over the years and to continue to advise the business during new high stakes and pivotal moments.
SG: I find one of the hardest things to do when people have been at a place for a certain period of time, is to resist the, “oh yeah, we tried that before” thing. You tried it six years ago in a totally different context. How do you prevent that?
JA: We tried a lot of things that didn't work because we had the wrong business model. It turns out we were right about a bunch of the things, but it was the wrong moment, wrong incentives, wrong unit economics, wrong scale, wrong whatever. As a culture, we are really open about that and encourage people to get curious about why things didn't work instead of writing them off. We try to start from a place of “what’s different about the context or opportunity now?”
We also created a Slack channel dedicated to learning from our history and not having to relearn lessons or repeat mistakes. Anyone can go into this channel filled with long tenured people and ask: “Does anyone have any history on why we did this, or didn't do that?” There's a constant curiosity and ‘learner’s mindset’ we try to instill and reinforce.
SG: When did you take on internal comms?
JA: Probably around 2013 or 2014. It was early.
SG: That's almost 12 years of doing that. How has internal comms changed? What was the impact of owning that relatively early and through this serious change?
JA: It’s a blessing we had a strong and established internal comms program in place, because one of the first things we had to do at the start of the turnaround was tell the company—of about 1,000 people at the time—that our business model was not sustainable and we had to make some serious changes. We leveled with everyone, told them we had a pricing model that was working against us, showed them the metrics, the problem, the vision for the new model, and the path to get there.
It was a delicate balance of galvanizing the company while also steeling them for an uncertain journey. We told them it was going to be hard, but it would be rewarding when we got to the other side of it, and they would all have had a hand in making it happen. The turnaround wasn’t linear—there were a lot of ‘oh $%!#’ moments, sleepless nights, and grey hairs sprouted—but we kept communicating our way through them all.
That held the team together and contributed to our success, and it is still core to how we operate today. We are transparent, we level with the org, we focus them on running fast at our biggest challenges and opportunities. Internal comms, at its best and highest function, is strategic alignment at scale. It keeps people focused on the right things, brings them along, and gives them context to make good decisions in their respective areas.
SG: Was there a function in internal comms that was more of a listening device versus a broadcast device?
JA: I wish I could say it was something more sophisticated and scaled back then, but it was just being in the trenches with everyone, having an open door and an open ear, and being a trusted team people could come talk to about anything.
A lot of what we started doing, we're still doing—but we have evolved it. For instance, we do this really special thing at the end of the year, which sounds cheesy, but it is a beloved tradition. It's called the ZVAs, the Zocdoc Values Awards. It is part award show, part recap of the year, part strategy rollout for the year ahead, part variety show, and part company roast. It’s a 90 minute, fully produced show in a theater with lighting cues, tech and dress rehearsals, even tuxedos—the works. It's unanimously one of the best days of the year for Zocdoc’rs.
When I started, it was mostly just an award show and very tops-down. As we were going through leadership changes, culture changes, business model changes, and more, we needed an emotional release valve. So we renamed it, and we shifted from having an exec host to two non-leaders taking the mic. We turned it into a roast of our leaders and a sharp, funny recap of the year’s highs and lows. I half-joke that as Zocdoc has become more successful, it’s a much harder show to produce because there is so much less to roast. It was actually an opening joke at the ZVAs in our first year of profitability that the show wasn’t going to be funny anymore; as the revenue and EBITA increase, the show’s jokes-per-minute decrease.
But it's an intentional part of our culture to demonstrate that leaders are fallible, that we can celebrate our successes and openly embrace our missteps.
SG: If you can all get into a theater and make fun of leaders, that's an environment of a relatively high trust. You mentioned trust as an unlock. I want to hear you explain the value of that as a skill in the comms leader ‘basket of needs’ that you have to have to be successful. But I also would love to understand how you advise people to actually go about attaining that because it's one of those classic easier said than done things.
JA: There are lots of important traits for a comms leader to have, but none of them matter if there isn’t trust. People aren't going to seek your input or take your advice, you aren’t going to be able to influence outcomes, protect the company, maximize opportunity or see big ideas through (like, for example, a 90 minute variety show slash company roast).
I can't say this holds true at every organization, but I think I have gained trust at Zocdoc in a few ways. First, by speaking truth to power and saying the hard but necessary things that help the business, the org and the culture move forward in a positive direction. I feel grateful to be part of a team that welcomes and rewards that. Second, I try to give people choices and tradeoffs. There's almost never one right answer, rather a set of choices that you can make that each come with risks and opportunities. I really try to help clarify what we are optimizing for and then articulate the choices and tradeoffs that can get us there. This feels more collaborative, you get buy-in and bring people along. Lastly, I put the company first and take myself, my ego and my pride out of it. People know I want the best outcome for Zocdoc, and I'm not being political or trying to jockey for anything for myself.
Of course, I also earned a lot of trust by showing up, stepping up, and being a steady hand during very hard times. Then over time, you start to create a track record of success, and hopefully you're right more than you’re wrong.
SG: There are moments where you are talking to an executive and you feel like this could go either way – I'm not sure the person I'm talking to fully believes what I'm saying, their experience of comms is maybe different, or they're new here. You just catch a vibe and this vibe makes me uncomfortable. I'm not sure I have this person right now. How do you call out those situations to make sure that you are actually capturing the trust?
JA: I'm keen to run at the spike, in a disarming way. I'll just say, “Hey, I'm noticing X, Y, Z. Can you tell me more about your experience here?” or “I'm sensing this, or my read on the situation is this, or tell me more about that view or why you're feeling that way.” Questions are always a good way for me to learn more and adjust my approach. I love context and information. It helps me navigate and adapt.
SG: The saying part is key. Because the more you leave that stuff aside, it just builds up over time and becomes this thing you have to work against. And then you're like, how did that big wall get created there?
JA: Yes. This is also where the choices and the tradeoffs come in. Framing things like, “Both of us want X. There's a bunch of ways we can get X. Here's my view of the paths to X and what the good and the bad things are about that path.” Obviously you have to pick and choose battles; you don't want to die on every hill. But it takes time to build trust with new people. They say ‘trust comes on foot and leaves on horseback,’ which is true.
I also recognize that the trust I’ve earned (and work hard to keep) from others in the organization does not magically extend to new people who join. It’s never set and forget it. You have to proactively build and maintain trust.
SG: A hard thing to understand, for people who want the job that you have, is how much of the role is actually managing other executives or whoever you report to. Relative to managing a team, managing all the other opportunities, the comms work, the strategy, the tactics and all that, how would you balance those out in terms of your priorities and what you need to get right?
If you're talking to someone who is a number two or someone who wants to get into this role of Head of Comms, the assumption is, I'm going to be running a team. I'm going to be going out and doing all these fun, interesting things in the world. I'm going to be executing and doing the strategy. Then there's this moment of realization that actually a lot of your job is managing the other executives, so they understand the context around what you're doing and where you're going and then basically signaling out. I'm curious how that evolved for you. What advice would you give to others who take the role for the first time?
JA: I do a lot of executing. But if you're just executing and you're not thinking about your CEO and your executive peers as important stakeholders where you can add value and help support their goals and the business’s goals, you're missing a really big opportunity. It makes you better at your job when other leaders want to knock on your door and say, “Hey, I have this tricky thing going on and I want your advice.” Or “I have this idea about an interesting thing my team is working on, can I run it past you?” It’s just such helpful glue that pays off in the long run.
A lot of what I'm doing is trying to connect dots across what's happening in the business, and I get a lot of input from my peers to inform my view. I’m also playing back to them how the business’s priorities inform my team’s priorities, what we are doing or not doing and why. What are the most important things that we need to be paying attention to, preparing for, taking action on—from how we communicate internally to how we show up in the press, on the Hill, and in the market.
It feels natural now—many of us have worked together for over a decade. But in this chapter, we’re bringing in new leaders with fresh eyes. I think a lot lately about how to integrate our history with new perspectives and experiences. Both are really valuable.
SG: This is not unique in professional services types of work, but you spend your entire career doing the “work” and then suddenly in this moment you're like, whoa, you have to actually do executive management. No one's trained to do that. There's comms people who have good people skills, but I wish there was more formal training in terms of how you actually do this and do this in a way that not only is generic to general management, but also specific to how to apply it to a comms framework.
JA: It is management, but it's also…counseling's probably not the right word in the therapeutic sense, but there are times it can feel close to that.
SG: So much of our job is family therapy. Every family is screwed up and probably could use some work. Every company certainly can too. There’s not a company that exists on this planet that couldn't use a little therapy work. Generally sometimes that comms person is the person who takes that role and, like I’ve said, becomes the chief alignment officer. Once you can peer into people's souls, and I mean really, truly, once you can get to that point of truth, core truths of who they are and then who the organization is, how does that impact what you can bring to life from a comms perspective?
JA: You want to go with what's already there. What are they really interested in? What are they concerned about? What's authentic to them? That's become such a buzzword, but how can you embrace that and make it an asset for them? Our founder and CEO is German. He’s a former physician, from a 300 year family tradition of physicians. He’s a technologist. He worked at McKinsey. He is a voracious reader. He can also be self-deprecating and funny and we lean into that, internally. It really works for him. It helps make him approachable and builds trust with the org.
SG: As opposed to making him into some sort of archetype that he isn't.
JA: Right. If you can harness that once you get to know people, it can become really powerful. Oftentimes, ‘thought leadership’ starts with a content marketer or a comms person instead of asking: What's actually on your mind? What do you really think about this? We can be moving so fast that we forget to even ask those questions, but these people are in their positions for a reason. If you have that open line and you have permission to ask slightly more probing or personal questions, that really helps things stand out.
SG: What is your general advice to people who are looking to follow a path like yours?
JA: I once managed a woman who was amazing. She was like, here is what is going to happen in my career: I went to X school, and did Y job, and now I’m doing this job, then I’ll go to business school, then I’ll do XYZ. I wrote her a recommendation for business school. She got in, she went down that path. I'm like, wow, incredible to behold—and not at all how I function.
There's pros and cons to being path directed and to being open minded. If I had been path directed, I probably would have said no to a lot of the opportunities that came my way at Zocdoc. Or I wouldn't have thrown my hat in the ring.
My advice is: be flexible, be fearless, and normalize not knowing. I’ve learned a lot by figuring things out as I go, Googling (now ChatGPT’ing) stuff, and asking people smarter than me to coffee; it’s the cheapest tuition ever. I’ve also learned what I like, what I don't like, what I’m good at, and what I’m not good at. And I've given things away that I haven't been as good at or haven't enjoyed as much. And that's okay. Stay open and try things. I still don’t know what I will be when I grow up—and I’ve come to love that.
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