A Baby Boom in the C-Suite: How a new generation of leaders is redefining working motherhood

Six women gathered around my kitchen table a couple of weeks ago. They ate slices of fancy pizza, sipped glasses of bright rosé and talked about their dreams for The Big Life, that delicious cocktail of career, love, ambition, respect, work, and money — on your own terms.

 And then, as the dishes were being cleared and we picked at the last crumbs of dessert, one of the women, a 33-year-old entrepreneur with a new business plan and a book project on the horizon, leaned in closer and asked me the question that was really on her mind. “How do you navigate having a big career and having babies?”

It’s a question that’s been asked dozens of times around my table. For the last four years, I’ve hosted dinners for hundreds of men and women at my home and across the country. There is always a moment when these young, hungry, ambitious women drop their guard and confess what they are most worried about.

“I feel like I am just beginning my career in so many ways. I want to be able to travel, spend time with my new husband and really give my career 100% before I have to take care of someone else,” the entrepreneur explained to me later. “So many women in my family have halted their careers to become moms and never picked them back up. So, there is a fear there that if I pursue work and kids simultaneously, that I might let my career slide. Can full attention really be given to both?”

Millennials are the most highly educated generation in recent history and the opportunities they have to succeed at work have never been greater. Forget work-life balance. For this generation of women, it’s all work all the time, all life all the time. In fact, Millennial women are the driving force behind the current jobs recovery.

But when work is at the center of your life, that changes how you look at everything else — relationships, money… and motherhood, which women are pushing later and later.

Often, young women tell me that they are afraid to have big ambitions for their family and for their careers, as if there’s a harsh penalty for even wanting to succeed at both. What’s even more striking is how often I hear them say that they don’t have role models for how to make work and family work. They look up the corporate ladder and tell me they see only a few females at the top, many of whom do not have children or who have had to perform a contortionist act to work as if they don’t have children. They see senior male executives who seem un-burdened by the daily pressures of family life. 

And so I cheered out loud in late March when Jennifer Hyman, 38, co-founder and CEO of Rent The Runway appeared in Fortune to celebrate the billion-dollar valuation of her company, with her nine-month baby bump proudly on display in a bright yellow Derek Lam dress (available on renttherunway.com, naturally!). It was as if she’d sent out a flare to all the young, ambitious women that said, “Look, I’m doing it, you can do it too.” She wasn’t carefully hiding behind her desk or a stack of books or asking the photographer for a tighter shot. She was unabashedly pregnant and, with a billion-dollar company underneath her, unabashedly powerful.

If this doesn’t seem revolutionary, flash back to 2012, when the newly minted Yahoo CEO Marissa Mayer announced she was pregnant—the first pregnant CEO of a Fortune 500 company. She was immediately celebrated—and castigated. The opinion pieces screeched: Could she manage such a rigorous job during her pregnancy? Was her decision to take just “a few weeks” of maternity leave setting a bad example for women? And how would she handle the life and body changes that come after a baby is born and continue to be an effective CEO? “What if her baby has colic? What if Mayer battles postpartum depression?” Time asked nosily and with disdain.

This was the cultural bonfire that was burning when I was pregnant with my first child in 2012. Every family decision is personal, of course, but suddenly mine carried this extra, public-facing weight. I’d spent decades building my career in media — putting partnership and children on the back burner. I’d been editor-in-chief of Seventeen for nearly five years when I finally had the security of a partner and a cushion in my bank account to feel ready to start a family. It was competitive at the top of the masthead, and I didn’t want anyone to think pregnancy would blunt my edge. At first, I hid my bump behind scarves and under my desk (you should have seen the ridiculous gymnastics we had to perform to hide my belly during the taping of a reality show!) I refused to hire an “interim” editor-in-chief, lest anyone think I wasn’t fully in control. I worked from home straight through my first maternity leave and my second, 18 months later. Stacks of papers were dropped at my apartment every night and returned the next day. I never missed a conference call. There wasn’t a cover I didn’t personally hone.

But what seemed like a hard-working badge of honor then feels frantic now. I was afraid that if I took time to heal and bond that I’d be out of the game. I was afraid I would be admitting to some kind of professional defeat.

Perhaps my fear was well founded. One widely sourced and terrifying statistic says 43% of highly qualified women leave their careers after having children. 

For her part, Rent the Runway’s Hyman has said she’ll take a full four months of maternity leave, leading by example for her team. And she’s not the only young female CEO who feels a responsibility to celebrate her working motherhood.

Katia Beauchamp, 36, co-founder and CEO of Birchbox, spent 100 days last summer on bed rest with her fourth pregnancy, but closed a significant partnership with Walgreens as she was being rolled into the operating room for a high-risk delivery. “What makes any leader great is perspective, and there’s no way to explain the perspective that having children gives you,” she told me. 

Alexa von Tobel, 35, legendarily sold her company LearnVest to Northwestern Mutual for $250 million on a Wednesday and had her first baby the following Sunday. She had another baby while she was in the C-suite of that giant company. And just a couple of months after announcing a new venture fund, Inspire Capital, she had her third child. “Life throws so much stuff at you. It throws illnesses at you, it throws parent illnesses at you…. Having a child is such an invaluable life milestone, but I see it as any other event in your life. You can’t plan for the unexpected,” she said in an interview for my book, The Big Life. “It’s better to have a life strategy that says we’re going to roll with the punches when they come.”

As Julia Collins, 40, founder of $2.25 billion-dollar start-up Zume Pizza, was raising money in Silicon Valley, she was acutely aware that she was often the only woman, the only person of color, and certainly the only person in the room with “a big beautiful pregnant belly.” “Just like I am unapologetically feminine and unapologetically black, I was unapologetically pregnant, and I brought it into the conversation,” she says. “I lead with it. Hello, here I am!”

Amy Nelson, 39, founder and CEO of co-working space The Riveter, currently pregnant with her fourth child in four years, has raised $20 million and has opened seven locations of her women-centric co-working space in the last 22 months alone, with another eight locations set to open this year. “I talk about motherhood as a strength,” she says so firmly that you can almost imagine that she’s flexing her bicep. “Being a parent has made me ruthlessly efficient with my time and it’s given me a different empathy that is really important to building a corporate culture. It’s time that people see this differently.”

Stacy Brown-Philpot, 43, CEO of TaskRabbit, says being ambitious in your career is actually a benefit to working moms, she explains. “I have found that while responsibilities increase as you progress in our career, so does the level of flexibility. So, don't assume it gets harder as you go up. If done right, it will get easier.” Brown-Philpot adds that the partnership of her husband “mattered more than anything else,” to help her to continue to rise at work while they built their family of four.

Shadiah Sigala — 34, a mother of two, and co-founder of child care concierge service Kinside — tapped into her frustrations with the expectation that she’d have to opt out of start-up life. “Demand it all and expect it all,” she says as a rallying cry for the next generation of women. “Bang on the table, raise our voices, don’t let anyone tell you you’re too entitled. That’s how change happens.”

And while they might seem like the superheroes among this generation of working mothers — swooping in to save us from unrealistic cultural expectations and slow-moving corporations — many of these women say their decisions to have children were just as emotionally tumultuous as the women who have sat around my dinner table.

“I had such ambivalence about becoming a parent for many years,” says Zume Pizza’s Collins. “At the core of the ambivalence was actually fear; that if I pursued one path, the other would be excluded for me.”

As an ambitious corporate litigation associate at a big white shoe firm, The Riveter’s Nelson says she saw no well-trodden path to becoming a partner and a mother. “I started looking up [the firm’s hierarchy] and wondering where the women were and where the mothers were.” In fact, it was this bleak law-firm dynamic that sparked the idea for The Riveter, a female-focused space where ambition and babies could co-exist. “I built The Riveter because I wanted to be a member,” she says.

Beauchamp says that she had some early trepidation about telling her investors that she was pregnant out of fear that they’d see her as less dedicated to the start-up. “It’s not just men who presuppose your priorities change. I see it happening woman to woman, too.” Beauchamp says. “Duh, your priorities change! The notion that your priorities changing makes you less good is where it gets dangerous. Your priorities changing makes you better. Because you have more of a reality check.”

Sigala tells me that it’s part of her crusade to reject the super mom narrative that, for a select few, having a strong career and family life is somehow easy or seamless. Instead, it’s more of a constant work in progress. “Yes, I am doing it all, but my marriage is occasionally on the fritz and I get post-partum depression on and off. I feel that I have responsibility to talk about these things.”

It’s a responsibility that Nelson feels too: “My mom moved in with my husband and me, I have a full-time nanny and I have a village of people around me,” she says. “This isn’t cheap, it’s not magically easy, but it’s doable if you make the decisions that make it workable.” 

My own mentor and career role model often repeated the previous generation’s idea of how work and motherhood should co-exist. “You can have it all,” she has said. “But not at the same time.” It was meant to make us feel that anything was possible — but, well, you know, not really.

That binary way of looking at the world made me even more discouraged. How exhausting to have to think about the pieces of your life in isolation — work only when you’re working; family only when you’re not working. How do you sustain a career if you have to opt out for children? How do you maintain a happy family if they must be pushed aside as you flex your ambition? It’s paralyzing and, frankly, not realistic. 

We need to see women who lead big, messy, complicated, overwhelming, but satisfying lives — in all arenas. We need to see women who have challenged the status quo and who have carved out space in the world that fits all their ambitions — in both family and work. And we need them to light the way for the generation of young women who are following them into the professional world.

Rent the Runway’s Hyman is paying her influence forward to her employees, offering all hourly employees the same bereavement, parental leave, family sick leave and sabbatical packages that full-time salaried employees receive. She also took a stand on covering birth control for her employees — so they can more easily start families on their own time frame. 

At Birchbox, Beauchamp says that her focus is on managing expectations in the transitions between work life and new parenthood. “It’s a predisposed expectation that your career should be slower, or you should plateau — that’s the problem we’re focused on,” she explains. “We spend a lot of our efforts around training managers for off-boarding and on-boarding people back into work, so they aren’t making career decisions about the rest of their lives in the first six months after returning from a big life change.”

With her women-focused co-working space The Riveter, Nelson is vying to build a utopia for working moms. “I’m building a company whose mission is to change the future of work for women,” she says emphatically. “We only schedule company meetings between 10am and 3pm. We give 16 weeks of paid parental leave and we welcome babies in arms up to six months at work and at all Riveter locations. Starting a business is really hard and having a family is really hard. We want to create an environment where people can find a community.” 

In creating childcare service Kinside, Sigala says she’s trying to build a solution for working moms at all levels of corporate America. “The conversation that’s maddening to me is, ‘Where are all the women? Why is the pipeline so skinny?’” She says. “It’s because child care, dummies!”

The work-motherhood tension isn’t going to dissolve overnight or with any one solution. These women are forging new territory and starting the conversation — and it’s up to us to continue it. We shouldn’t only be talking about the fear that babies will derail our careers over pizza or after a glass of wine. These are conversations we should be having regularly, with our colleagues and the other women in our life. We need to know that we’re not alone. We need to shore up the support we need from partners, friends, and yes, our jobs, to continue to achieve and succeed — in all areas. 

“We’re the first generation of women who are going through this new pattern where we look at becoming parents much later, we think about love and partnership and settling down much later,” says Collins, who has just launched AllRaise with the mission of supporting female founders and funders. “It feels really scary because there wasn’t a generation ahead of us that did this in this way. But for the next generation — if you do your job and I do mine — this will be a much happier process for them.”

Ann Shoket is the author of “The Big Life.”