December 12, 2019
CEO Spotlight: Meet the Co-Founders of Winnie

We're delighted to present the next spotlight in our series of CEO. This time, we're talking to a kicka$$ duo: Anne Halsall and Sara Mauskopf, Co-Founders of Winnie. They are running and leading the fast-growing business and team at Winnie. If that wasn't enough, they each have two young children and both are expecting a 3rd child in early 2020. Oh, and they've raised $9M in the process. We're inspired by the hustle and determination to make a seamless app for modern parents and their dedication to their families. It's an incredible team and we're thrilled to have them part of Team Bloomwell. 

Happy Reading! 


First, tell us about Winnie! 

Winnie is a marketplace for child care and early education. We help over 4M parents across the United States find daycare and preschool. We started Winnie because we both struggled with finding child care and realized there wasn’t a destination you could go to and learn about all your options. Winnie has all kinds of information you can’t find anywhere else like whether a provider has open spaces, reviews from parents who sent their child to that provider, and prices.


Co-Founders in Bloomwell: Anne Halsall (in Mockneck Dress- sold out!) and Sara Mauskopf in the Julie top.


How did you two meet? 

We met at Postmates. At the time Sara had just come back from maternity leave after having her first child and Anne had two young children. We bonded over some of the challenges we faced as working moms. We also both have a background in product and engineering so we couldn’t help but nerd out about technology we could build to help parents. We got so excited that we quit our jobs to start Winnie!

You recently closed a $9M Series A round- congrats! Meanwhile you're each growing your business while growing humans! Can you share with us how your pregnancy is shaping this stage in your business? What feedback or insights have you seen from your team, your investors, or your user community?

For each of us this is our third child so we feel like pros at this by now. Our team at Winnie and our investors have all been super supportive. We told both groups really early on because pregnancy is something to be celebrated and we wanted to set the example that women can absolutely grow and raise humans and be awesome at their job at the same time. 


Werk Werk Werk: Sara Mauskopf (in Elizabeth Blouse) and Anne Halsall (in Mockneck Dress- sold out!) 

What do you think is the secret sauce/ special advantage of having two female co-founders? 

We have seen a number of folks tackle the child care space and fail. I think a lot of these founders see big dollar signs because it’s a massive market, but they are missing the actual pain points that parents face because either they are not parents themselves or they don’t take on the majority of the child care burden themselves. It’s not necessarily being women that is our secret sauce but more that we are parents and have directly faced these child care challenges ourselves.


How are you thinking about parental leave? 

Parental leave is really important but it’s only a small part of what it means to support working parents. When we set out to build Winnie, our goal was to create a family-friendly startup where parents could do meaningful work while being awesome parents. Some examples of our family-friendly culture are we don’t work nights or weekends, we provide work from home and flexible work, we encourage everyone to take a generous amount of vacation, and we have an epic lactation room. As far as parental leave, we believe it should apply equally to men and women, at the birth or adoption of a child and should be fully paid. At Winnie, every employee gets 12 weeks of fully paid leave.

What is your biggest work challenge right now?

Prioritization! We are growing so fast and know there are a million and one things we can build to help families and caregivers so it’s always a challenge to figure out what to do first.

What has been an a-ha moment (either good or bad) as you’ve launched Winnie?

When we first started Winnie, we didn’t know that we were going to build a child care marketplace. We started by building a product that helped parents with a number of different aspects of their lives. What we found from our community was that everyone was trying to use Winnie to find daycare or preschool. This was the big a-ha moment for us — we realized that connecting parents with high-quality, affordable childcare was the most important & meaningful thing we could build.

Who’s your current Female Founder or Female exec crush?

We love Amy Nelson from The Riveter. She’s a mom of 4 which is already super impressive by itself and has not only built her company while growing her family but she also advocates for other women.


Hot Seat Questions!  

What Bloomwell piece would you choose first or give to your BFF?

Sara: I’m obsessed with the Elizabeth Blouse. I wear it with leggings and it’s instantly fashionable. I get compliments all the time (even my daughter was like “wow mom you dressed up”)

Anne: Same. I don’t care if I’m wearing the same outfit as Sara. It’s a great outfit. I would wear it everyday if I thought I could get away with it. 

If you have an hour to yourself…what do you do?

Sara: Oh that’s easy. I’d sleep.

Anne: Womanly bath. Candles, bubbles, trashy novel. The full nine yards.

Superpower: invisibility or super strength?

Sara: Super strength. I’m going to need to be able to lift 3 kids at the same time!

Anne: Super strength, no question.

Best book you’ve read recently?

Sara: Super Pumped by Mike Isaac. 

Anne: The Broken Earth trilogy by N.K. Jemisin.

Favorite vacation spot?

Sara: Disneyland :-)

Anne: Disney Aulani. Your resort stay includes childcare… need I say more?


Huge thanks to Sara and Anne! Check out Winnie and follow Sara and Anne on Twitter!