Sara Mauskopf  is the CEO and Co-founder of Winnie. She has a background in consumer technology and product management, having worked at Postmates, Twitter, YouTube, and Google. She graduated with a Computer Science and Engineering degree from MIT. She lives with her daughter Bryn and her husband Eric in San Francisco. Today we chat with her about working at startups, building her own startup, and what it meant to become a parent throughout it all.

Have you always known that you wanted to work and have babies? Did you want to do both at the same time?

SARA: I always assumed I’d have children one day, but for most of my life it seemed like something I would do in the very distant future, and I put very little thought into it. Around the time that I turned 29, it really hit me that I wanted a child in the near future. However, I never thought for a second that I would stop working . I just assumed that I’d continue at the same pace and trajectory I had always been on.

How did pregnancy change the way you worked?

I felt pretty nauseous in the first trimester of my pregnancy. By the third trimester I had gained over 50 pounds and was extremely uncomfortable, but I tried not to let any of that slow me down. It was actually pretty easy to continue at (mostly) the same pace I’d been working  because I was still child-free!

How did your mindset around work, motherhood, and babies change when you became pregnant?

They didn’t really. It took caring for a child to realize the magnitude of the life change I had made. Honestly it’s still constantly changing because my daughter grows so fast and each stage is so different from the stage before. I’m constantly learning and needing new information. Just as soon as I think I have a handle on things, everything changes. That’s the amazing thing about being a parent.

What was something that surprised you about being pregnant?

The second trimester was actually really magical for me. I felt wonderful and got a big burst of energy coming out of the first trimester. It’s a nice little respite in the middle of pregnancy that I will definitely look forward to and take advantage of if I ever get pregnant again!

How did your mindset around work, motherhood, and babies change after the arrival of your kid?

Having a child inspired the idea for my company, Winnie. It made me realize that caring for a child is a job, and one that deserves great tools and technology. Shortly after having a child, we started Winnie to make parents’ lives easier. We realized that parents need information, and connecting them to other local parents and local information was the best way we could help them with the challenges they faced.

What was the hardest thing about being pregnant that you wish other people knew?

All pregnancies are different so I definitely don’t speak for all women when I say that I was able to continue life as usual with some modifications, (like wearing more comfortable clothing and being unable to travel towards the end of my pregnancy). To many people at work I looked very different, but to me I was exactly the same person with the same drive, maybe even more. 

“I would encourage people who work with a pregnant woman to treat her the same as you always have and not assume she wants to slow down because she is pregnant.”- Sara Mauskopf (CEO and Co-founder of Winnie)

What is something true about being a parent that you wish more people understood?

Caring for children is a job — one that is too often assigned to women, and too often considered invisible and inconsequential. It deserves great tools and technology just like any other important job.

What do you wish was more common in startup culture or western business culture?

SARA: I don’t think many startups are very family-friendly. Many tech companies measure your performance by the amount of time you spend in the office or they require participation in nighttime events or worse, off-sites.

“At Winnie, we’re building a different kind of startup. We are led by women, have a majority-female engineering team, and the importance of family is built into our culture. We don’t require our employees to participate in work events outside of normal work hours and we bake in flexibility so they can work from home, or odd hours if they need to.  We measure performance by results, rather than the amount of time spent in the office.” – Sara Mauskopf (CEO and Co-founder of Winnie)

What was maternity leave like for you? How much time did you take off? Who designed the policy?

I took 6 weeks off and it was the right amount of time for me, but that doesn’t mean that it’s the right amount of time for all parents. There was no formal policy in place at the time.

How has being a mom transformed you? How has it transformed the way that you work?

Being a mom has made me a better worker. Because I have limited hours in the day to work, I’m forced to prioritize and really focus on what’s important. I don’t waste any time on low-value tasks. I probably spend more time working than before I had a child, because I am not wasting time.

How do you think work has influenced the way you parent and raise kids? What do you hope to share or teach your kids about work?

I am not cut out to be with my child 24/7. As much as I love my daughter, I need a substantial amount of time to myself to recharge. Having a break from parenting (yes I continue “working” to get a break!) allows me to be a better mom when I am with my daughter.

What are the most helpful and supportive practices you’ve taken on during the journey into motherhood and entrepreneurship?

I like to spend the weekend really focused on doing things with my family. We explore local parks, play at our favorite children’s museums, go out to eat, or just cook meals together as a family. This time helps me recharge for the week and also gives my daughter focus and attention that she doesn’t get from me during the week when I’m exhausted after a day’s work.

What is the most frustrating part of owning or working at a startup or small company?

SARA: Taxes and paperwork. I hate that stuff, but I have to do it!

Conversely, what is the most exciting thing and appealing thing about working at a startup or small company?

I love working with an extremely talented team of engineers that I was able to build from scratch. It’s amazing what you can achieve when you work with people who are more talented than you.

Do you believe startups need to work 60-plus hours a week to make their work happen?

No, in fact I believe it’s detrimental. When you work 60+ hours a week, it means you are probably not prioritizing and picking the most important things to work on. I think it’s better to work a 40 hour week but be laser focused on the things that move the needle for your business.

Any advice for other women or new parents out there?

SARA: It can be especially hard for working parents to get the information they need to be successful. I know this firsthand! A lot of information is offline, locked away in private mother’s groups, or learned through trial and error. That’s why we built Winnie. We want to easily connect parents to a local network of parents for information, advice, and recommendations, as well as help them find great places to go with their families. I’d encourage all parents to download our app (it’s definitely not just for moms!) and get access to the help they need. It definitely takes a village!


This essay is part of the Startup Pregnant Interview Series asking women and men about what it means to birth new businesses, grow in leadership at work, and bring new people into the world.

These interviews seek out the personal details as a way to inspire new thinking about what it means to be pregnant, to go through physical and emotional transformations, what it means to be your most creative self, and how that influences work as we understand it today. Outdated cultural thinking about what work looks like and traditional gender roles leave both men and women tired and searching for a different kind of meaning.