A Game-Changing Solution for Solo Moms


A Game-Changing Solution for Solo Moms

Image credit: Winnie.com

An interview with Winnie founder Sara Mauskopf

A single mom who ventures out with a baby in tow faces myriad uncertainties: Where can I nurse my baby? Where is the nearest changing table? Which restaurant has high chairs that don’t look like they need the attention of a hazmat team?

Worry not. Tech veterans Sara Mauskopf (right) and Anne Halsall (left) have created Winnie, an app that takes the stress out of traveling with your little one.

Whether you’re planning a fun family outing or you’re caught in the middle of a mall with a preschooler who needs a restroom stat, Winnie gets you the 411 you need, ASAP.

(Note: Winnie cannot predict when your infant will spit up on your work blouse or warn you that your baby is about to have a diaper blowout to end all diaper blowouts in the checkout line at the grocery store. Some uncertainties will remain . . . uncertain.)

Recently Winnie cofounder Mauskopf talked with ESME about her new venture, her strategies for balancing CEO and mom life, her reflections on the tech industry, and her advice for Solo Mom entrepreneurs.

Q: What is Winnie?

A: Winnie helps parents and people who care for children find great places to go with their kids. It can help you find something to do on the weekend, tell you whether a restaurant has a kids menu or a changing table in the restroom, or show you a great spot to breastfeed your baby when you’re on the go. In addition to helping parents find great family-friendly places and activities, Winnie can help you find a daycare or preschool. It also has information for parents of older kids, such as reviews on schools, museums, and activities.

Q: What inspired this venture for you?

A: I started Winnie in January 2016 with my cofounder, Anne Halsall. I had recently given birth to my daughter, and I realized there was so much information I needed to know about where I could take her and what I could do with her. Did my favorite restaurant have a changing table in the bathroom? Was there anywhere indoors I could take her to play nearby? Winnie provides this information and more. It helps parents find great places to go with their children. It gives them local information from other parents about schools, doctors, playgrounds, and so much more.

Q: How will Winnie be useful to Solo Moms?

A: Parenting is a full-time job, and Solo Moms know this better than anyone because they are doing this job by themselves. The idea behind Winnie is to make this job easier by giving parents access to information that was hard to get before. We also want to enable parents to go to more places and do more things with their children. As a Solo Mom, you can’t necessarily just leave your kid with someone else while you go out to dinner. Finding places you can go comfortably with your child is key.

Q: At ESME, we define a Solo Mom as a mom who, by choice or circumstance, finds herself doing most or all of the parenting in her home. Recently your husband’s cancer diagnosis left you doing most of the parenting in your home. What has it been like for you, balancing CEO life and mom life, while supporting a spouse who is undergoing cancer treatment?

A: It’s been really hard! But from the beginning, we set up Winnie in a way in which we could be flexible and adapt to the fact that people had lives outside the office. This made it possible for me to work even during a crisis because I didn’t have to be in the office 24–7. I also had to be creative about how I got my work done. I pitched to venture capitalists from my husband’s hospital room. I took interviews and meetings while my daughter slept. It wasn’t easy and didn’t always go perfectly, but I was determined to figure out how to make it work.

Q: What was particularly helpful to you during this challenging time?

A: One thing I did a lot was say no. If someone wanted to “catch up” over a cup of coffee, I’d ask if we could do a phone call or e-mail instead or say I couldn’t do it at all. Saying no to things that were a waste of time was huge for my productivity. I also said no to things such as throwing my daughter an elaborate birthday party. Saying no is actually something that I want to keep doing even though I’m not in crisis mode anymore.

Q: Many women experience workplaces that are inhospitable to their roles as parents, especially as Solo Moms. Tech start-ups are notorious for expecting all-in, 24-hour-a-day dedication from their employees. This work culture can exclude Solo Moms, missing out on their perspectives, talents, and expertise. Winnie operates in a more sustainable way. How is the work culture at Winnie different?

A: Both my cofounder and I are moms, so from the beginning we knew we wanted to build a different kind of start-up. We work 9 to 5 (or 10 to 6, in my case), and we don’t work on weekends. Our weekends are really sacred time that we spend with our families. It’s really forced us to prioritize and focus on what’s important.

Q: What can tech companies do to support a sustainable work-life balance for Solo Moms?

A: I think the number-one thing companies can do is be flexible. Parents definitely have things come up—your nanny calls in sick or your kid has to stay home from day care—and workplaces need to accommodate that in order to retain top talent. We treat our employees like adults, and as long as they get their job done, it’s OK if they aren’t in the office all the time. Parents are some of the most productive employees you can have because they don’t waste any time, so figuring out how to retain them is just good business.

Q: Entrepreneurs pitching parent-related products to potential funders face a unique set of challenges. What challenges have you faced in procuring funding for your project? How have you overcome those challenges?

A: We’ve had to pitch not only our company but also the work parents do. A lot of the people we were pitching to (male venture capitalists) did not think this was a real problem. Even the ones who had children weren’t necessarily the primary caregiver, so they didn’t understand the unique challenges parents face. We had to work doubly hard to prove ourselves and our business. I think the standards we were held to were much higher.

Q: What advice do you have for Solo Mom entrepreneurs who have a vision they want to bring into reality?

A: Go for it! The number-one reason so many parenting companies have failed is that people work on it as a side project. This is not a side project for us. We are taking this space extremely seriously and giving it everything we’ve got. I’d encourage Solo Mom entrepreneurs to take their vision seriously and do everything in their power to bring it to fruition.

Q: Anything else you want us to know about Winnie?

A: We now have an iPhone app and an Android app. I’d love for Solo Moms to try Winnie and let me know if there is anything that could make it more useful to them. I love to hear from parents and how they’re using it because it helps me make sure I’m building something that can be useful to all parents, not just myself! You can reach me at sara@winnie.com.


Cheryl Dumesnil, ESME’s LGBTQ Resource Guide, is an author, educator, writing coach, all-around do-gooder, and one of two moms separately coparenting two amazing boys. You can follow her on Twitter at @cheryladumesnil.

Please feel free to contact us with any comments or questions.


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