A Week in the Life: Sara Mauskopf of Winnie

Winnie is a caregiving marketplace designed to make it easier for parents to find daycare and preschool options that meet their needs. Founded in the Bay Area in 2016, Winnie is now available in cities nationwide. We asked CEO and cofounder Sara Mauskopf to share a glimpse behind the scenes.

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My cofounder Anne Halsall and I met in 2015 when we were both working at Postmates. I was a brand-new mom at the time and Anne had two young children. After I came back to work after maternity leave, we both bonded over our challenges as working moms. We discussed everything from childcare to breastfeeding. Having both worked for various great tech companies, we realized that the world class engineers we were used to working with were not working on solving problems for parents.

We saw a big opportunity to bring technology to parenting with over 90% of new parents being millennials and used to having technology at their fingertips.

Me and my Winnie cofounder Anne Halsall in our board room. We had our hair and makeup done for the photoshoot, which is one of the more glam parts of being a founder. Most of the job is not as glamorous. As a CEO my job is to fire myself from (almost) every job I'm doing. Either I need to get the work to a point where it can be handed off to someone else, or I need to decide it's not worth our time as a company to focus on. That means lots of meetings with my senior staff, external folks, and email and Slack galore!

Here I am currently very pregnant with my third child. I’ve been trying to document more of my day-to-day life on Instagram stories because I want people to see you absolutely can be a mother and a CEO at the same time. So, of course, I need to take a selfie first thing in the morning!

These are my girls in my kitchen at home. I try to hang with my kids in the mornings for a bit before I go to work. It’s hard during the week to spend a bunch of time together (and I’m usually also trying to get ready for work or doing chores at the same time) but I try to make our mornings and evenings really count.

Here is a Winnie team meeting in our cafeteria. We’re based in the Mission in San Francisco in an awesome, homey office space. Most of the Winnie team works in engineering, product, and design roles. We're building a pretty complex platform under the hood to match parents with childcare providers. The easy-to-use interface for parents and providers is all made possible by the incredible team we have.

Printing a new banner for Winnie at a local print shop for before we head to CES. Now that Winnie is a national product used by parents all over the United States, we’re finding more value in attending larger events where we can get in front of people who may not have heard of Winnie from just word of mouth or finding us online.

My kids running to hug me as I arrive home. They are the best fan club ever and also very competitive — I wonder where they get that from :-).

With my kids on the weekend at a local museum. We try not to have too many scheduled activities on the weekends so we can spend time together as a family and meet up with friends, discover new places, or just hang out at home and relax.