When Sheryl Sandberg published Lean In in 2013, Meetup CEO Scott Heiferman ordered several dozen copies. On March 11 — publication day — his female employees spilled off the elevator into the company’s light-filled Soho headquarters and found that they’d all received an email from Heiferman, inviting them to pick up copies of the book. At first, they were excited. Their boss cared about their career advancement. Then they noticed that none of the men had gotten copies. The mood turned. Because, please, did the job of helping women succeed at work fall to women alone?
“I got my ass handed to me,” Heiferman remembers. “Like, what the fuck, Scott? You give it to women, but it’s supposed to be men who are reading this.”
That was only three years ago, but back then, Meetup was a different company. Heiferman founded it with four others in 2002 to help people with common interests — being witches, owning great danes, supporting Howard Dean—meet up IRL. The service had been adding users steadily since the start. Organizers paid a small fee, and by 2013, the company had broken even or turned a profit for many years running.
But when Heiferman looked around at that trusted team that built his company, he realized that, yes, most of them were white men. “I remember looking at these venture capital websites that listed all men and going to CEO summits that were all men, and being judgmental about that,” he says. “Then I would come home and look at my own team and say, ‘you know, wait a minute, this is predominantly male-filled company.’” It was something he wanted to change, but just as with his well-intentioned but poorly received decision to hand out Sandberg’s book, he had a lot to learn about how to actually catalyze a shift.
This is a familiar issue for many companies, but it’s particularly acute at tech startups, where technical skills are prized and speed is paramount. They’re started by founders who, in the push to assemble capable and comparable staff, hire people they know—often people who look like them. By the time founders are on steady ground and ready to think about building a diverse leadership team, they’ve already cemented a culture of sameness. “Folks who have the background, talent, and interest and come from diverse backgrounds don’t have the relationships with people in the tech sector,” says John Rice, who runs the nonprofit Management Leadership for Tomorrow, “so they don’t come in on the founding teams.” The result is a paucity of women and people of color in companies’ senior ranks. Only 18 percent of the top management positions, or c-level positions, at companies are held by women, according to McKinsey’s 2016 Women in the Workplace Report. Women of color only hold three percent of those senior positions.
Around the same time, Heiferman was facing another significant issue: the company had taken on the complacency that often comes from having successfully figured out how to solve its first big set of problems — appealing to users and making money. Though Meetup has never lacked vision, it was falling behind on execution, and it ran the risk of missing the shift to mobile altogether. Investor and startup guru Ben Horowitz talks about peacetime and wartime in business. During times of peace, a company has a large advantage in its market, and that market is growing; during wartime, the company is fending off existential threats that arise through competition or changes in the market. Meetup was operating as a peacetime company, when in truth, it was wartime.
Heiferman needed to do what on its face seems like a really simple thing—to reshape the team of people who run Meetup. Across the country, CEOs are being told that now is the time to make this simple shift. But in practice, it’s not as simple as we want it to be: it requires founders to look hard at what qualities they value in their employees and question the very practices that built their companies. Things like, do you fire the friends that helped you build your business to make room for new blood? Where do you find all these women if they’re not people in your network? That’s why, for all the talk about the importance of diversifying tech, most people aren’t doing it.
Three years later, Heiferman has transformed his leadership team. Three of the company’s seven senior executives are women, including the vice president of product and the chief technology officer. Five of Meetup’s 11 directors are women — meaning that eight of the 18 most senior executives at Meetup are women. It’s not perfect: Meetup still has a long way to go in recruiting minorities. But this new leadership has had a powerful effect on corporate culture, adding, Heiferman believes, a sense of urgency that has spurred a new direction for the company.
How did they do it? One very deliberate step at a time.
Meetup’s founding story echoes those of many tech startups. “You pull in the people you know,” remembers Brendan McGovern, a cofounder who is the chief financial officer. McGovern is a hulking guy with a warm sense of humor who leans forward in his chair when he talks. He met Heiferman just out of college during intern orientation for their first and only corporate jobs, at Sony. In the mid-1990s, they built an ad agency called i-Traffic that they sold to Agency.com before they started Meetup with another friend. Says McGovern: “You’re thinking, ‘who are the right people I know in my head who have the skills I need at this very moment?’ And then you’re off to the races.” Back then Meetup employed one senior woman, who ran sponsorships and had risen to vice president, but she left in 2012 when Meetup changed direction and ended sponsorships.
By then, Meetup’s managers were realizing that their homogeneity had become a disadvantage. “We started to hear it in all the team surveys,” says McGovern. Adding a more diverse group of people to the leadership team wasn’t just the proverbial right thing to do — it became a strategy for keeping the company’s team of engineers and product people happy and engaged.
But it was hard. As new opportunities came up, Meetup’s management team leaned on its recruiters to find diverse candidates to interview. But the recruiters weren’t delivering a broad enough set of promising candidates. And even when potential leads surfaced, Heiferman found that recruiting them was a challenge. At one point, Heiferman identified a promising person for a c-level position. She told him she wasn’t interested because she didn’t want to work for a man. “She was a really good candidate,” says Heiferman, “and this was a startling thing.”
But he noticed something else. Though Heiferman had been struggling to locate diverse recruits, Meetup’s systems engineering team—a heavily technical group of engineers that Heiferman calls “some of the nerdiest of the nerds”—had grown to an eight-person group that included many people of color. It had an African American leader. Those employees told Heiferman that they had interviewed at a number of companies, but chose Meetup because the systems team wasn’t all white.
Heiferman brought up his challenges at a portfolio day for Union Square Ventures. The room was packed with mostly male CEOs. He shared the feedback he’d received from the woman who turned down the job. “The tone in the room was aghast,” Heiferman remembers. “And I said, this is a problem! A diverse candidate pool is not going to apply to your company because they don’t want to work somewhere that is all straight white dudes. And then what’s going to happen? Your applicant pool is going to be only straight white dudes, so you’re going to hire more straight white dudes. And the more you keep hiring straight white dudes, the less likely that not straight white dudes are going to apply.”
In 2014, Meetup’s vice president of product moved to Colorado, freeing up one of the most important roles in the company. Heiferman launched an exhaustive search, and he prioritized doing all that he could to find diverse candidates.
McGovern suggested that one of the best candidates already worked at the company: Fiona Spruill. She had known Heiferman a long time, but she’d started at Meetup just a few months earlier. Spruill had spent the previous eight years managing web and mobile coverage for the New York Times, where she’d hired 80 percent of the newsroom’s digital staff, championed mobile development, and helped launch the global edition of nytimes.com. When she had first interviewed at Meetup, the team wasn’t sure what she should do, but they recognized that the company could benefit from her strong management background. They put her in charge of Meetup’s international expansion.
When Heiferman approached her about the head of product position, Spruill was surprised. She didn’t have a traditional product background. “If you looked at my resume, I had ‘editor editor editor’ all in my title,” she says. When she was interviewing for jobs with tech companies, Spruill says that the issue came up: “They’d say, ‘why do we want to hire an editor?’” But she, too, believed Meetup needed to be operating as a “wartime” company, focusing on how to launch products more quickly to keep up with a fast-changing market. She’d had experience building and managing just such a culture at the Times.
Filling an important position by focusing on skills rather than title isn’t rocket science. I called Stanford’s Caroline Simard, who is senior director of research at The Clayman Institute on Gender Research, to ask her about this, and she said that one of the best ways to add women to the senior ranks at companies is to promote them from within. Often, she said, we don’t. “You have to ask, ‘Who do we take a chance on?’” she said. “One way bias creeps in is that we hold women to a higher standard.” We assume men will succeed at a job, even if their background suggests they need to learn some of the tasks, whereas we are concerned women may not succeed unless they’ve done the job before.
Spruill started the new role that August. It wasn’t an easy transition. She was still getting used to Meetup’s startup culture. She’d come from a newsroom, which she described as the antithesis of Meetup’s tech-centric way of doing things. “It’s all about informed judgements,” she says, versus leaning heavily on data to make decisions and testing them. Also, she was replacing someone with deep product expertise. By contrast, she wasn’t able to be involved as closely in product decisions, because she didn’t have as many years of hands-on product experience, and because she was spending more of her time on other aspects of the job.
But Spruill brought skills no one else had at Meetup. Specifically, she’d hired 45 people over two years at the Times as it expanded its web newsroom. Her first focus was on recruiting new talent. “It had been sort of delegated to the recruiters and not thought of as a core part of what senior leaders at the company were supposed to do,” she said. Thanks in part to Spruill’s leadership, that began to change.
By 2015, Heiferman realized the company needed a new chief technology officer. The former CTO, who had been with the company for 12 years, was “the smartest engineer in the room.” But he didn’t have the management experience or the leadership vision to grow the engineering team or imbue its members with the sense of urgency that would motivate them to launch new products faster. Heiferman’s friends and advisors pushed him to prioritize management experience in his next hire. He needed someone who knew how to lead. He asked his recruiting firm for female candidates, and they weren’t forthcoming. “They said, ‘for CTO?’” he remembers. “I said, ‘I’m paying you a lot of money and you have to deliver me a female candidate. That’s what I’m paying for.’”
Still, Heiferman wasn’t seeing the talent he wanted. A few months into the search, he traveled to San Francisco to interview candidates. A college friend had just had a baby, and he stopped by to visit. The friend’s wife worked at GitHub. As they caught up about life, Heiferman asked her who she’d most enjoyed working for. She pointed him toward her former boss, Yvette Pasqua.
Pasqua was not looking for a new job when Heiferman called. She’d recently taken a job at a New York-based company called Tinypass, which built paywall software for publishers. But she’d heard of Heiferman, who is a well-known figure in New York’s tech scene, and she’d used Meetup. Upon finishing college in 2004, she’d moved to the Upper West Side and gotten her first dog, a pug named Arthur. She’d never had a dog, so she used Meetup to connect with a group of pug owners in Central Park. She agreed to meet Heiferman for a coffee, although she didn’t think she’d be qualified. “Most of the time when companies that aren’t big yet are looking for a CTO, they’re looking for the best architect or coder in the room,” she said. She was a talented engineer, but she’d spent many years building teams by that point, and had been less involved day-to-day in coding. “I’m not that person. I’m better at the management stuff.” Heiferman explained that he was looking specifically for management experience.
He was sold on Pasqua immediately. She had grown technical teams, and she had proven herself to be very good at motivating people and getting them to communicate well. Pasqua came in to Meetup three more times to meet with the leadership team. The entire process took about six weeks, during which she estimates she spent about 20 hours with Meetup’s executives and engineering leaders. She saw that Meetup had a significant vision of social consequence for what it was trying to do, and as she got to know the engineering team, she had ideas for what it needed. Also, she could see the leadership team was eclectic. Yvette had talked to Google and Facebook about jobs in the past, but her career path was nonlinear. She’d worked at an agency. She’d moved to Costa Rica for several years. And she always felt that they were wondering, why did you to all this weird stuff? But at Meetup, she found a team that was interested in her varied past. “I had found my people,” she remembers.
For their final interview, the Meetup team planned to meet Pasqua at a restaurant for dinner. At the last minute, McGovern suggested they come to his house instead. McGovern lives with his partner in a Hell’s Kitchen apartment with a backyard that had a koi pond. Though McGovern doesn’t come out and say this, Pasqua is pretty sure he made the change on purpose. “At the time, I actually think my about.me page said, ‘I enjoy my wife’s home-cooked food and the company of friends more than anything in the world,’” she says. Pasqua joined Meetup exactly a year ago.
Stanford’s Simard suggests Heiferman did a number of things right here, too. First off, she says, he didn’t delegate the job of sourcing good candidates to recruiters. He tapped his personal network to find nontraditional candidates. Second, he found someone who wasn’t looking for a new job. “Often, the narrative is, ‘well no one applied,’” she says. “But he said, ‘the talent is out there and I need to go and seek it out.’”
Of course, making the hire alone does not equal success; Meetup’s team needed to support Pasqua in making the transition and succeeding at her job. All of her direct reports were men, and they were used to a more hands-on manager. But the transition was less difficult than she thought, a fact she attributes to the culture Heiferman had cultivated at Meetup. In her first few months on the job, she made four director-level hires — two men and two women.
These days, Meetup feels like a wartime company — a company focused on relentlessly changing its service before competition and market changes eclipse it. Sales jumped 30 percent last year, and the company’s users rose 20 percent to 28 million, but that doesn’t feel satisfying to Heiferman. Heiferman wants to see Meetup grow to a quarter billion users, a goal he considers reasonable.
Late on a Friday afternoon in September, I stopped by Meetup’s office. The company was about to announce a full rebrand and overhaul — its first significant rebrand in six years — to help the service appeal to a broader, younger audience. The new app introduced a new browsing experience offering more intelligent personal recommendations and a simpler design, and making it easy for people to find events, RSVP, or start a Meetup. Pasqua’s group had rewritten its iOS app completely in a new programming language. The energy was high.
The rollout was scheduled for September 28, which was just a few days before Spruill was scheduled to give birth to her second child, and she was determined to see the company’s launch arrive before her own. (It did, by two weeks.) Indeed, on the day I visited, it was nearly 5 pm and no one was packing up yet to head out for the weekend.
Heiferman credits Spruill and Pasqua for generating the urgency Meetup needed. “They brought something we have not had,” he says, pointing out their strong management experience in larger organizations.
By one measure, Heiferman’s big push to diversify his management team seems minuscule: he made two hires over the course of a couple of years. And he is the first to say that the company has a long way to go. Right now, leadership team is entirely white. But if tech’s startups are really serious about diversifying their companies, this is how it happens: deliberately and often maddeningly slowly, one-by-one, starting at the top of the organization. Those two hires have spawned a shift in how the rest of the company looks, and, more importantly, how it operates. “Everybody wants the magic bullet, the magic app to solve this, but that’s not how these things happen,” says Stanford’s Simard. “Small wins are everything.”
