‘Pitch the Immeasurable’ and Other Leadership Tips

‘Pitch the Immeasurable’ and Other Leadership Tips

It's not easy making the transition from manager to executive. One Medical VP Marketing Vanessa Hope Schneider shares the lessons she leans on from her marketing, PR and publishing days that have helped her become a better leader.

Eventbrite. Airbnb. Vanessa Hope Schneider has helped grow some of the household names in technology. But if you ask her about an executive who's made a lasting impression on her, she summons the name of Louise Brockett. Those in tech may not recognize the name, but Brockett is the long-time executive director of publicity at W.W. Norton, an elite book publisher. But to Schneider, Brockett was the institution.

“She was my first boss. In many ways, we’re opposites. Here I am in SF in my high tops and my big earrings, thinking of Louise, who hails from the Upper East Side and is put together in Brooks Brothers,” says Schneider. “But that’s not really what I mean when I think of how she showed up. She’s a portrait of grace, cool-under-pressure, pragmatic and beloved by others. I recall how she dealt with big personalities, how people listened when she spoke, and how attentive she was to her team. In my current role, I often think: What would Louise do?”

Now the VP of Marketing at One Medical, Schneider has long since transitioned from publishing to tech, having held senior PR and communication roles at Eventbrite and Airbnb. But she still calls upon lessons from both industries as she leads her team. In this exclusive interview, Schneider explains how she uses tenets of marketing and observations from publishing as an executive — and what marketers can lean on as they transition to leadership roles. Let’s begin!

1. Commit to a book, but write in chapters.

Authors often have the arc of a story in mind, but get there one chapter at a time. When it comes to taking on your first executive marketing role, enlist the same mentality. Sketch out your vision for your role, but recognize that you’ll fulfill it in stages. For Schneider, this has meant setting reasonable expectations for herself at the onset, starting with her first year.

“I think it’s really important to be realistic with yourself. If you’re a straight-A, gunner type, you’re going to want to get in the role and see immediate, seismic impact. But the truth of the matter is, it’s rare that a new leader can make such sweeping change on behalf of an entire organization,” says Schneider. “So I gave myself three goals for my first year. If I fulfilled these three, I’d not only keep myself focused, I’d make my priorities clear as I built relationships with my team.”

Here’s what Schneider outlined as her three prime concerns over her first year — and how she’s tackling them (see tips 2-6 below) with tactics:

  • Learn — or relearn — the industry. For Schneider, joining One Medical meant educating herself on a new team, company and industry in parallel. But even those switching companies within an industry are wise to brush up. There’s an entropy that naturally happens when you’re in a role or at a company for a long time. It’s why savvy professionals attend choice industry conferences, read broadly and tap into advisors outside their network to absorb and apply outside perspectives.
  • Survey the landscape. This is less to pick-off easy ways to have an immediate impact and more to hone in on what’s front and center for your team. It’s easy to think of your appointment as a starting point for all involved, but you’re joining a team whose story is already in motion. For Schneider, this goal entails getting a detailed, data-driven and nuanced understanding of the short-term priorities and opportunities for her team.
  • Show and earn trust. The importance of trust — and the candor and conversations needed to foster it — need not be rehashed here. Building trust is a thread — and effort — that’s woven throughout your role and career as an executive. Best to start early.
The narrative doesn’t always start at the beginning. Your page one is someone else’s page 120.

2. Start with the index.

Too often people forget that joining a company also means getting intimately acquainted with its industry. To get smart about an industry quickly — and your company’s role in it — Schneider recommends a few 1:1s with your founder or CEO. Don’t ask for the origin story (read: table of contents), but get them to start at the index: a list of what’s important, organized for comprehensiveness, not chronology.

“As any marketer knows, you need to represent your company. As an executive, you will represent your company and your industry, even if it’s your take on it. So you need to be able to speak with a reasonable level of authority on the sector,” says Schneider. “For an executive new to a role and industry, this takes some serious upfront work. In addition to reading hundreds of pages about how health insurance works, I tapped into the mental archives of [then CEO and founder] Tom Lee over a series of 1:1s.”

This tactic is helpful for any new hire starting at a company, but is requisite for an executive on a leadership team. “It doesn't matter how good you are at the discipline you represent, at the end of the day, you need to learn the ins, outs and influencers of your industry. For Eventbrite, I learned every ticketing platform under the sun. At Airbnb, that meant knowing all about travel. And now at One Medical, it means being fluent in what care options exist,” says Schneider. “Ultimately, there are two relationships to focus on at the start: how your team fits into your company. And how your company fits into the landscape. The CEO has those cliff notes. I spent a lot of time on the phone with him before I even got started in the role.”

3. Draft each character as the protagonist.

After the series of 1:1s with her CEO, Schneider issued an assignment to everyone on her team. “I asked each person to make a ‘lookback’ for the second half of 2016. I joined in early 2017, so this allowed me to do three things. First, to get a sense of how last year ended for the team. Second, to get an understanding of their individual contributions and challenges. And, third, to employ a sneaky way of getting people to express themselves in their own voice,” says Schneider. “I did the lookback as much to know what everyone had to share, as how they shared it. It’s a path to how they perceive their work and how they see opportunity in their role.”

What your people work on speaks to what’s immediate. How they describe their work signals their vision.

Cemented by her comms, marketing and PR background, Schneider is ever curious about how people communicate. “I’ll often ask candidates or new hires: ‘What book are you reading right now?’ It’s not because I’m gauging their taste. I’m interested in how they present a plot. It tells me a lot about how they think,” she says. “There's a big difference between someone who can summarize a plot linearly versus someone who sprinkles bits and pieces — in a cloud or a circle. The style in which people communicate their own work gives me an idea of how to connect to them, and better link them with each other. It also indicates if they have the ability to frame and contextualize business problems and opportunities, especially in a complicated space like healthcare.”

Aside for a way to identify thought process, an exercise like a lookback is especially vital for new executives leading teams at early-stage startups. “There’s a very common structural challenge for companies at earlier growth stages. In many cases, everyone on a marketing team is pretty much the only person who does the thing they do,” says Schneider. “There’s a real opportunity for an executive to help connect the dots. That’s what the lookback allows. Then it’s my job to see how they fit together and get a sense of the structure I’m inheriting. To my team’s credit, they’re very collaborative and curious about each other’s work, so there were natural overlaps and connections. But that’s not always the case.”

Vanessa Hope Schneider

4. Earn trust by calling out a POV, inflection points and BS.

Schneider is not the first nor the last to assert that trust takes time. “Earning your people’s trust is not fully achieved by any clever hacks or claiming to have seen it all before. So far, I’ve found three ways that have worked well in garnering trust,” says Schneider. “First: it’s better to be clear and sometimes wrong, than be indecisive to avoid being incorrect. The key is to have a point of view, express it clearly, bring others into your thought process and solicit feedback. So it's not about earning trust by seeming infallible, because, of course, no one is. Being wrong reminds people you’re human and builds empathy. Being right prompts a track record and also garners trust. In short, where trust is concerned, the goal is to advance the conversation to a decision, not to originate the right choice every time.”

Second, to foster a sense of trust with your team, you need to call out inflection points — and they may not all be good ones. “One of the things that I noticed when I first got here was that the team was accustomed to working from home on Fridays. And I felt that it was one of my responsibilities as a leader of the team to be our team publicist. I’m representing them and I need to make sure that other leaders in our company know — and see — the great work they’re doing,” says Schneider. “So when I took my role, I said to everyone: ‘We’ll work from the office. Five days a week.’ It did ruffle some feathers — and I had one-on-one conversations with anyone who wanted to speak with me about it, where I learned that it was a logistical challenge for some, and others had ‘understandings’ that they’d work from home a day a week. But I elaborated: ‘I’ve learned that people outside our team don't know enough of what we do. I will work hard to be a megaphone myself, but we need to show them collectively. This is a publicity campaign on behalf of our own team.’ Most people got it, even if they didn’t like the change initially. The point is that, with context, it wasn’t punitive or arbitrary.”

Third, be the first to call out BS. “People can smell BS from a mile away. At Airbnb, giving information — good or bad — to hosts requires authenticity, pragmatism and directness. You can’t spin it or wrap it in marketing speak and have that be sufficient. Hosts won’t stand for it,” says Schneider. “And so similarly with one’s team, I think there's actually a nice parallel, because it can be very tempting for new executives to only deliver the good news — and just gloss over the unpleasant and uncomfortable. Cut that out. Your people will trust you more when you do.”

If you’re always selling good news to your team, people will stop buying it. Promise you. Don’t glide past the lows.

5. Represent the relationship.

For much of her career, Schneider has worked on two-sided marketplaces. Whether it’s event attendees and event hosts at Eventbrite, guests and hosts at Airbnb or patients and providers at One Medical, she’s developed a relationship with, well, relationships. It’s so ingrained in how she works that she recognizes quickly when something’s gone awry with a key stakeholder.

“One of our early ads at One Medical featured an image of someone with a runny nose. The caption said: ‘That won’t go away on its own.’ The implication being that, if you’re sick, come into One Medical,” says Schneider. “Now while that’s a clever, memorable ad for a potential member or a current patient, providers had concerns. One asked: ‘Do you see the issue? In this case, it’s likely the problem will go away on its own. It’s a cold. If members come in with those symptoms, I’d very likely tell them to rest and that it’ll go away on it’s own. A visit isn’t the best course of action or use of time for both the patient and doctor.’ Marketing must represent the relationship — both sides — authentically.”

Now, in many ways, witty, cheeky ads like that were an essential part of One Medical’s early growth. Now, Schneider is pushing the team to create marketing campaigns that showcase the personal relationship between patients and providers. “Michael Jordan is to Nike what the providers are to One Medical… they’re our heroes,” she explains. In short, hold the relationship in highest esteem. “When I think about the disparate stops on my career path — at publishers, Eventbrite, Airbnb and One Medical —  the thread is an interest in people connecting,” says Schneider. “And that core interest informs my approach to leadership.”

For Schneider, being an effective executive goes beyond giving people the ‘why’ — that’s basic leadership jargon 101. It’s finding ways to reflect the relationship within and between teams. “At Airbnb, more often than not, when a host or guest was unhappy, it was because they genuinely didn’t know what it felt like on the other side of that relationship,” she says. “The same phenomenon translates to executive leadership. With my team, I need to explain what’s a priority at a leadership level and contextualize it so they understand. And similarly, I need to articulate to my fellow leaders, ‘Hey you're not seeing the marketing team move this number for this reason.’ The only way to engender empathy is to represent the relationship I have with each cohort — and by doing so, draw a clear line connecting leaders throughout the organization to my team.”

6. Pitch the immeasurable.

Stay in marketing long enough and you’ll get the question. That’s right. The one asking you to measure your impact or gauge the ROI of your efforts or quantify the ripples made from each campaign. “Some of it is unmeasurable. But don’t let that make you shy about it. Because, on the flip side, the unmeasurable is often immeasurable, and that’s frequently what gets people really excited. Because very often, that’s the emotional,” says Schneider. “It’s the story. It’s about people. And human beings actually like doing human things. I think about PR as one of those disciplines: you’ll never be able to concretely measure the impact of press coverage. It's just not gonna happen. So how do you get people excited about investing in, focusing on and validating PR, appropriately?”

That’s where marketing executives need to market marketing. “That instinct informs the way I think about marketing leadership. I know what it's like to be the person in the trenches, who is trying to advance a discipline that is often unmeasurable. I know what it's like to be the one who's doing the thing that could be written off as fluff. And I know what it's like to try to get people excited about all of that,” says Schneider. “The best marketing leaders embrace the showmanship, merchandising, and roadshowing of marketing. I recall being the beneficiary of those efforts. And so I take it really seriously now that it's my job and role to do that for others: to pitch the immeasurable. That’s why I will go to any team, and give the same presentation I've given an infinite number of times at other teams’ meetings, if it helps progress the agenda of the marketing team.”

Dear colleague: let me pitch you the immeasurable — and why it matters.

Tying it Together

Schneider’s days working on book tours and drafting marketing copy are behind her, but she still draws on principles from publishing, PR and communications in her role as an executive. Among them: commit to the book, but write in chapters. In other words, your narrative as a leader unfolds; even if you’re ambitious, remember to take it year by year. Flip to the index to get a suitable synopsis. Most seek origin stories. But if you want comprehensiveness over chronology, look to the index: your CEO. To get to know your team members — and their voices — ask for a “lookback” that allows them to be the protagonist of their story. Earn trust by calling out a POV, inflection points and BS. Steward the relationship between leadership and your team. Lastly, unabashedly pitch the immeasurable to anyone who’ll ask and listen.

“I think the biggest difference between being a ‘manager’ and a ‘leader’ is going from a position where you're accountable for strategy that is within the realm of your expertise versus being accountable for strategy that extends beyond your direct experience. For me, marketing has always been about being curious about how people identify and gather — and about what relationships people choose,” says Schneider. “As marketers, we already feel driven to connect people to a new experience, one that’s beyond what they know. Those uncharted territories are areas to explore; as an executive, you truly own them. That’s an exciting prospect for anyone.”

Photography by Bonnie Rae Mills.