Amid a Childcare Crisis, These Founders Offer a Solution

BY sagelazzaro | May 22, 2020

Welcome to She Leads, a series digging into the good, the bad, and the ugly of being a woman in business. In each piece, we chat with a different founder about her experiences, the issues women face in business, and how they’re powering through in the face of adversity.

Sara Mauskopf didn’t know she'd be launching a data-powered childcare platform when she left the tech giants for good. All she knew was that she, along with millions of other parents, had a big problem, and no one was trying to fix it.

“I had worked at a bunch of really awesome tech companies with great engineers,” said Mauskopf, who spent time at Google, YouTube, Twitter, and Postmates. “And I just saw that the amazing engineers I had worked with weren't really working on solutions for parents. Actually, no one was working on solutions for parents at the time.”

So Mauskopf, along with her Postmates coworker Anne Halsall, took matters into their own hands and launched Winnie in 2016. Mauskopf serves as CEO and Halsall as chief product officer. To date, they’ve raised $15.5 million to fund their venture. (And they now have two children each.) Childcare providers use their platform to fill their open spaces, build their wait lists, and get support and resources to run their businesses efficiently. Parents benefit from the platform’s detailed listings, which include descriptions, photos, tuition information, licensing status, availability, and more.

The founders’ belief is that childcare needs to be more accessible, and technology is the way to make it happen. Their mission is especially critical in the midst of the pandemic, when the chronic problem of unequal access to childcare in the U.S. has become a full-blown emergency. Mauskopf’s message is now front and center: childcare is vital to the economy, it’s an incredible amount of work, and it’s disproportionately put on women.

We chatted with her about the origins of her company, the blind spots of venture capitalists around women-led companies, and what the pandemic tells us about the state of childcare. Excerpts:

From Day One: The world still sees childcare as women’s work, including much of Silicon Valley. In my years of interviewing female founders, one thing I’ve heard time and time again is that VCs often question the ability of mothers to both run a company and have children, but never fathers. Have investors viewed Winnie as a company only relevant to women? 

Mauskopf: Everything you said has absolutely been my experience. A lot of investors said things like, "I'm already invested in the space." So we'd ask which company, and my favorite was an investor who said he just invested in a tampon company. I was like, "Well, that's not the space we're talking about. We're pitching a childcare company."

Oh my gosh. I’m speechless. 

In their minds, that company was the same because it was founded by two women like us. Tampons and childcare have nothing to do with each other. They’re as different as you can get, but I think that was the perfect example of how investors view a company in the parenting space started by two women. They were like, "This is a company for women. This is a company for moms," when really what we're doing is solving problems for all parents. We don't want women to take on the majority of the childcare burden. It's really important to us that this is accessible to both men and women, because childcare should be the responsibility of everyone.

I can't lie—my jaw is still slightly on the floor from that tampon comment, though I'm not surprised. Just yesterday I was just talking with someone about how investors often group companies that involve women together and consider them a niche. But women are diverse and they aren’t a small, specialized category; they’re half the population and drive 70% to 80% of purchases. 

Another surprising thing was that a lot of investors would ask, "Have you talked to X female investor?" Everyone wanted us to talk to Aileen Lee, who is a really prominent early-stage investor who started Cowboy Ventures and coined the term unicorn. She's an amazing person and we did talk to her, but she doesn't particularly invest in parenting companies. She wants to pick the most successful startups, whether they're founded by women or men. This was even way before she started All Raise [her non-profit dedicated to diversity in funders and founders]. Yet every investor was like, "You must pitch this woman because you're women."

After working at tech giants where diversity is lacking and the bro culture runs strong, how has becoming your own boss empowered you as a woman in tech?

When we started Winnie, it was very important to us that we started a company with a really different kind of culture. We wanted this to be a place where parents could work, where people of all backgrounds would feel comfortable, and most importantly, where we had work-life balance for not just us, but also our employees.

We made it a priority from day one, and it's just been really helpful in a number of ways. We've been able to recruit really top talent who maybe didn't want that traditional work-all-hours-at-this-startup-and-give-your-life-to-this-company environment. Recently, it's also made us pretty adaptable to this pandemic, because we already have a remote-friendly culture that enables people to work from home when they want to.

What do you think this current moment in time with the pandemic says about our society's larger issues surrounding childcare? And can you tell me a little bit about what Winnie is doing to help?

Childcare is essential to a functioning economy, and I think we're all really feeling that firsthand now. This is the message I've been preaching for over four years, and finally, everyone is getting it because they can't work if they don't have childcare. And for the people who need to perform essential work, they can't work from home in the odd hours when their kids are napping. They just can't go into work at all.

We've responded by launching a portal to connect families who need childcare, either to perform essential work or because their state allows them to seek childcare with providers who have open spaces. Over half of the providers on Winnie are continuing to operate either to serve essential workers or to serve any families, and they need to fill their open spaces to continue to stay in business. It's really tricky to navigate, and so we've been spending a lot of time helping open providers operate safely and connecting them with the people who do need their services right now.

Do you think this will lead to a shift in the conversation about work-life balance, childcare, and the disproportionate role women take on?

On an optimistic note, there is definitely a conversation now about the importance of childcare. I'm glad that we're finally really talking about it in the media. There was just an op-ed in the New York Times that went viral and was about the toll it's taking on parents to not have access to childcare in this moment. But on a pessimistic note, I'm very fearful that when there's not easy access to childcare, it's women who take the hit. We’re already seeing that. Women are dropping out of the workforce, taking a step back in their careers, or taking leave from their jobs. How long will it take for their careers to recover from that? That worries me.

Is there anything else you want to add, or advice you’d want to give to other women looking to start their own company?

This is a great time to start a company. It feels like a terrible time, but I think it's actually a really good time. People who’ve had ideas but haven’t wanted to take the leap have now maybe lost their jobs. And the talent that they might recruit is now looking for opportunities. There may not be the same amount of venture funding, but there's certainly enough to get started. The world is changing, and people are rethinking companies that were successful without a second thought. Everyone is starting fresh. It's a good time to start something.

This interview has been edited for length and clarity. 

Sage Lazzaro is a New York City-based journalist covering tech, business, culture, women and diversity & inclusion. Her work has appeared in Refinery29, VICE, Medium, the New York Observer, and more. Follow her on Twitter here.

 


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Apprenticeships: a Classic Solution to the Modern Problem of Worker Shortages

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Because apprenticeships are jobs first and foremost–jobs that pay a living wage–not just training programs,” Ryan Craig, author of Apprentice Nation: How the Earn and Learn Alternative to Higher Education Will Create a Stronger and Fairer America, told From Day One. “They’re accessible to anyone with the potential and willingness to work hard–and much more accessible than tuition-based, debt-based college, or other training programs.”Causes of the labor shortage are many: A workforce quickly aging into retirement, the slowing of population growth, the burdensome cost of post-secondary education, lack of access to affordable childcare, and an increase in entrepreneurship. All of these have contributed to a shrinking workforce. As of January, the U.S. labor force participation rate is 62.5%. A couple decades ago, at the beginning of 2001, it was 67.2%.Employers are attacking the problem on many fronts. Some are pulling out the stops to retain older workers who might otherwise retire, and some are coaxing the semi-retired back to the office with flexible new arrangements. Others are dropping four-year degree requirements to broaden their talent pools, or bulking up benefits packages to include childcare, paid leave, and fertility benefits to attract and retain workers. Apprenticeships have joined that medley of solutions, with employers, advocacy organizations, and policymakers exploring and investing in the “earn-and-learn” model to fill talent pipelines from hospitality to healthcare to finance. Apprenticeships Beyond Blue CollarsApprenticeships represent a mutually beneficial way of hiring and training workers. Apprentices get on-the-job training, related instruction (often in a classroom or virtual classroom), and a paycheck all at the same time. Employers get the workers they need, trained to their specifications. In the U.S., apprenticeships are most often associated with skilled trades–it’s normal for plumbers, electricians, construction workers to complete apprenticeships–yet white-collar professions are only beginning to forge a connection with earn-and-learn programs. In 2020, professional services firm Aon announced that it would invest $30 million in its apprenticeship program over the next five years, with a goal of creating 10,000 apprenticeships in the U.S. within Aon and its partner organizations by 2030. In 2022, IBM committed to putting $250 million toward apprenticeships and other “new collar” programs by 2025.Aon’s program includes three tracks: insurance, HR, and IT. Apprentices take courses in insurance and business administration at partner colleges. Francheska Feliciano, the director of Aon’s apprenticeship program, told From Day One that career changers have found a home there. “We have found that those that thrive in our program tend to be career changers, but our program has a wide range of candidates with varied backgrounds, customer service, hospitality, or other service type roles.”Last year, the Biden Administration announced that it will invest $330 million to expand federally registered apprenticeships programs. In July, the Department of Labor awarded $17 million to expand existing apprenticeships and promote the model in new industries. In November, Maryland Governor Wes Moore committed $3 million to developing apprenticeships for public-sector jobs and $1.6 million toward the development of hospitality industry apprenticeships. “Maryland has set ambitious goals for expanding apprenticeship and we mean to meet them,” said Portia Wu, Maryland's Department of Labor secretary, in a press release. “Registered apprenticeship is key to our state’s economic success. We’ve already hit historic highs in apprenticeship adoption and today’s investments will accelerate our progress.”Alleviating the Local Labor ShortageApprenticeships could help solve local labor shortages for companies whose workers must be on-site–crucial for skilled trades like manufacturing or nursing–which are experiencing a pipeline problem of their own. Rather than recruiting the skilled talent from elsewhere, employers can use apprenticeships to develop the talent in their community. As housing inventory trails demand, employers who can tap their local talent markets will have the advantage, said Renee Haltom, the VP of research communications at the Federal Reserve Bank of Richmond, during a panel discussion last month at the Richmond Economic Forecast  “The regions that figure out housing are going to be ahead of the curve in terms of dealing with the coming demographic shifts,” Haltom said, referring to the aging U.S. workforce. Annelies Goger, who studies how to scale earn-and-learn models at the Brookings Institution, sees the advantages for local employers. Apprenticeships are a way to draw on local talent, and employers are more likely to retain locals than workers who have relocated, she told From Day One. “Rising rents have made it hard for employers to find and retain people only with the normal ways they’ve recruited people, so they’re looking into a lot of other ways and channels for finding talent,” Goger said. Apprentices Enter Finance and AccountingIn accounting and finance, more workers are retiring than are entering the field. According to a 2024 analysis by the U.S. Chamber of Commerce, “even if every unemployed person with experience in the financial activities or professional and business service sectors were employed,” the report reads, “only 42% and 44% of the existing job vacancies in these industries would be filled, respectively.”In 2022, the Association of International Certified Professional Accountants (AICPA) and Chartered Institute of Management Accountants (CIMA) launched the first federally registered apprenticeship for finance and accounting professionals, and in its first year signed up 17 employers from 15 industries, including healthcare, industrial gas, banking, and manufacturing. 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There just aren’t enough young people entering the field to balance out their retiring elders. One problem: the profession has a reputation for being, well, dull.To fill the talent pipeline, and help rebrand the profession, AICPA and CIMA have piloted a youth apprenticeship program in Maryland high schools, aiming to drum up excitement and interest in the field among young people.Customizing the Programs Organizations, employers, and educators have found ways to tailor apprenticeship programs to their needs. They’re not just for recruiting, they can be deployed for talent development as well. “With the digital transformation of our economy, tens of millions of jobs now require workers to use tools to build things–only the tools are digital and workers no longer need to wear hardhats,” said Craig, author of Apprentice Nation.Often, those skills are software related. Where hospitals and healthcare providers use Epic, marketers use HubSpot, and HR uses Workday. “Companies are increasingly demanding that applicants for these jobs already have these platform skills–skills which are much harder to learn in a classroom than on-the-job via an apprenticeship,” Craig said.“Apprenticeship brings an organic culture of learning into any workplace and helps business perform better,” writes Jean Eddy in Crisis-Proofing Today’s Learners: Reimagining Career Education to Prepare Kids for Tomorrow’s World. “An apprenticeship program breathes new life into workplaces and lets employers quickly tap into a culture of learning that so many now are desperate to build.”Scaling Earn-and-Learn to Quell the Labor ShortageApprenticeships are difficult to start, and they’re difficult to scale. Few employers have the infrastructure to both employ and train unskilled workers at the same time, and most require the help of intermediaries like the AICPA and CIMA, which provide the instruction and the infrastructure.While it may be a while before apprenticeships alone make a dent in the labor shortage, analysis of the success of existing programs is promising. Not only are retention rates high–Aon, for instance, retains 80% of its apprentices–the Department of Labor estimates that employers get a 44.3% return on investment for apprenticeship programs.“While traditional apprenticeships emphasized hands-on skill acquisition under a mentor, modern apprenticeships often integrate technology-based learning, including virtual simulations and online coursework, to complement on-site training,” said Katie Breault, SVP of growth and impact at YUPRO Placement, a recruiting firm focused on skills-based hiring. Finance and tech roles are particularly suited to apprenticeships, she told From Day One. “Industries undergoing digital transformation, for example, greatly benefit from such programs. They offer real-time learning opportunities, crucial for staying relevant in dynamic fields.”The problem with apprenticeships as a solution to the labor shortage is that we just don’t have enough of them yet, said Craig. Plus, in his estimation, they’re under-funded and under-marketed on both the demand and supply side. “Many young people and their parents think of apprenticeships as a ‘second tier’ option–if they think of them at all,” he laments in Apprentice Nation. White collar employers may be thinking much the same. Yet as investment continues and apprentices pop up in surprising places, like the finance department, enthusiasm may spread. “It certainly fits the accounting profession,” Fiore said. “And if it fits the accounting profession, my sense is that it will fit many professions.”Emily McCrary-Ruiz-Esparza is a freelance journalist and From Day One contributing editor who writes about work, the job market, and women’s experiences in the workplace. Her work has appeared in the BBC, The Washington Post, Quartz, Fast Company, and Digiday’s Worklife.(Featured photo by Amorn Suriyan/iStock by Getty Images)

Emily McCrary-Ruiz-Esparza | February 14, 2024