Sara Mauskopf is CEO and Co-Founder of Winnie, a marketplace for childcare. She worked for Twitter in its startup days, and in several product creative roles for Google, YouTube, and Postmates. In this episode, Adii and Sara talk about raising millions of dollars and transforming the childcare market with Winnie, early ambitions and adjusting to change, and creating a work/family life balance.
Often when introducing herself, Sara puts her best foot forward with Winnie. From the get-go, she feels everyone she meets is either a potential employee, customer, or investor, and she never wants to miss an opportunity to make a connection.
Just before founding Winnie, Sara had come back to her role at Postmates after maternity leave. She didn’t think that would change after becoming a mother, but she actually found that what she wanted to work on had changed. Working meant spending time away from her daughter, so it had to mean something. She wanted not just to scale the ranks of a company, she wanted her business to be purpose-driven.
Sara met her co-founder while working at Postmates. Both of them are parents; they took the leap together. At first she wasn’t sure she needed a co-founder, as she was used to working alone. But, she says, there’s no way they could have lasted without one another. Now it is clear that she needed the support of her co-founder and vice versa.
Her co-founder and their team have helped immensely in making working on Winnie sustainable for the long haul, which is important because their mission was to fundamentally change the way child care works.
The two co-founders felt they had such privilege from working with some of the greatest engineers at these big companies. And because of this privilege, they had the ability to work with this underfunded, undervalued childcare market and combine it with their knowledge of tech in a way that hadn’t been done before.
Privilege and opportunity compounds, and as Sara was determined to work on something that had meaning, Winnie was the perfect focus.
Sara has always been extremely ambitious. When she was in kindergarten, she actually became upset when the teacher did not assign homework. So upset that her mother had to assign her some just to assuage her outrage.
Her first job out of college was with Google, and all too quickly she learned how different a job was from school. Not having homework due or a test to study for made it hard to figure out what it was she should be working on.
“90% of the job is figuring out what you should be working on to achieve your goals.”
While founding Winnie in 2016, Sara’s husband was diagnosed with cancer. This, Sara considers to be the hardest moment of her life.
The initial thought in this situation would be to put Winnie on pause. However, that was not an option. Investors had just helped them raise money which helped them hire their first two employees. There was no way to stop or pause or reconvene later; they were now responsible for two other people.
After taking a break, Sara returned to find everything had run very smoothly without her. The team had just submitted their first version of the app to the app store, and it was this success that made her realize it was a team effort; it wasn’t all about her. She could feel comfortable delegating work and not obsess over her part in the equation. And most importantly, personal matters could come first.
This moment transformed the lasting culture at Winnie, focusing it to a family-based culture where life comes before work.
Juggling a new business, a new child, and her husband’s health, Sara understood just how important a family/work balance was and is. In this time she learned how to adjust and make things work, even in the least ideal situations—just like the whole world has been forced to do during the COVID-19 pandemic. Pivot.
Privilege has made adjusting easier, Sara recognizes.
Ability to adjust is a privileged way of feeling, Sara says. With a safety net, it’s easier to take risks. Like switching from Google to Twitter, which was only a startup at the time. Survival was the worst case scenario.
Sara and her team thought that after 4 years they had it figured out, and then COVID emerged. Suddenly, the way parents and providers think about child care has changed in the span of months. It has shown there is a lot out of your control, sometimes there is bad luck, sometimes there is failure.
The more times you fail, however, the more likely you are to find the one time you won’t fail.
“It’s not really at all about minimizing the number of times you fail, it's about maximizing the number of times you succeed. Which may mean you have to fail actually a lot more to hit that one success.”
A family-friendly team and business environment is a priority at Winnie. People are a massive component of Sara’s--and, ultimately, Winnie’s--journey. While being an introvert, Sara knows people are so critical every step of the way—this has been especially notable during the recent shelter in place order. She is dedicated to ensuring a family friendly environment at Winnie, where people are treated well.
“It's important to first think at a high level what your purpose and what kind of culture you want to create and be explicit about that.”
Once a company decides on what kind of culture it would like to cultivate, decisions become based around that cultural purpose. From there it becomes easier to figure out what way of doing things is best and what decisions should be made to align with those values.
Winnie’s family first culture is what made providing employees with generous maternity leave a no-brainer for the company. Culture and values work as a filter for decisions to promote the company’s ultimate vision or goal.
Becoming a parent really helped put things in perspective for Sara, in addition to having a sick husband. Parenthood magnifies things a million times, she says. It’s a huge deal when things happen to your kids, which has helped put what she does at Winnie into even greater perspective. She expects and understands failures and rejections for her risks; being a parent helps her be “chill” about work and failure, because it doesn't matter as much as her family and their happiness.
Parenthood has also helped her with efficiency. She didn’t realize how inefficient she was until she had kids, which has helped her prioritize what is important. While she works less than she ever has, she does the best work she ever has.
If Sara were to impart one lesson for her children, it would be for them to leave the world a better place than they found it, think beyond self and being the best, and focus on a purpose greater than themselves. With Winnie, Sara and her team transform childcare, for children who will ultimately transform the world.