Posted in Small Business Hacks | by: Kira Deutch

How an Anti-Startup Mentality Helped Winnie Grow to 100,000 Users

When Sara Mauskopf dashed back to work after maternity leave, she didn’t have any mom friends. After working at tech companies throughout her career, most of Sara’s friends were “young dudes,” a world away from her new life of less coffee dates, more playdates. Sara was exhausted, overwhelmed, and needed support. So she asked her co-worker, another mom named Anne Halsall, where she could get honest advice about childcare, what to do on weekends, and other nuggets of information. “You just kind of figure it out,” Anne told her. In that moment, they saw an opportunity. “If we don’t quit and work on this, who will?” asked Sara. “Or some dude will do it, and do it wrong.” They quit within a day of each other.

A year and a half later, Winnie, a Yelp for parents, now glows on the phones of over 100,000 parents in over 3,000 cities across the country. How exactly is Winnie winning so hard? By momming so hard.

Sara dished on how their “anti-startup” mentality has become their secret weapon when it comes to benefits, culture, and being able to get more done when the day is cluttered with responsibilities. “We’re doing a double experiment,” Sara explains. “We’re betting on the thing we’re building and the way we’re building it.”

Just say no… to happy hours. (But yes to other benefits)

Winnie is a six-person startup that doesn’t exactly look like one at first. The team has never ventured out for happy hour, they don’t fire off midnight Slacks, and there is no free lunch. But what does exist? A refreshing environment for people who want to nail the work they do and the lives they have.

At many startups, everyone is expected to be besties. From archaic hiring practices to events that are centered around drinking, it can feel like a lot of companies just want to find people like them who can chill all the time. “While that’s fun for young people, it’s off-putting to people with families or those who want to spend time doing other things,” says Sara. “So we took a different path.”

Start with the benefits that matter (and ditch the rest).

First, Sara and Anne listed out the benefits that mattered to them. It was a no-brainer: Comprehensive health coverage and flexible work arrangements were two necessities they needed to do their best work. So they decided to weave those two essentials into Winnie’s DNA. To sweeten their decision, cutting out a lot of the typical startup perks saved them a hefty sum, so they could invest it in things like quality health, dental, and vision plans for employees and dependants. “We rather spend that money on things that enable our employees to live better lives and provide for their families.”

The Winnie team also has unlimited time off, and they’re encouraged to use it (which isn’t always the case among companies with this benefit). In fact, a study from Project Time Off found that over half of Americans left some amount of vacation time on the table. At Winnie, that doesn’t fly. “Our brains don’t work well 24/7. You need time to rest and recuperate to be at your peak performance,” explains Sara. “So it actually makes a lot of sense.” Research also backs up our need for breaks throughout the day. Taking a breather makes you focus, prevents boredom from kicking in, and allows you to make more connections between the things you’re doing. The takeaway? Even if you’re tiny, flexible PTO may be something to consider.

But that’s just one of the thoughtfully selected perks Winnie offers. By going all in on the benefits that truly improve their team’s quality of life, the company is able to pour more money into each one. Instead of, for instance, pitchers.

Want to do more? Work less.

As a parent, you don’t exactly have pockets of free time floating around. Startups? Same story. At previous companies, Sara would eat dinner at work, do laundry, roll into the office on weekends—basically live there. But for most families, nights and weekends are sacred. “From the beginning, it was really important for us to build the company so it was unlike any other startup where you’re working crazy hours and never see your family.”

To do that, the entire team is expected to work fewer hours so they can do more with the precious time they have. It’s a little counterintuitive, but their no-workaholics-allowed culture forces people to hunker down on what they really need to do. People work during normal business hours and not at night—it’s that simple. They also have the freedom to step away when they need to in addition to using their unlimited PTO. “Preschool pickup or drop off? That’s cool. Just get your work done,” says Sara.

In practice, how do they get more done with fewer hours? Here are a few tips to GSD like the team at Winnie:

  • Stick to a routine: Upfront scheduling eliminates the need to second-guess yourself about what you should be doing at any moment. With a routine, you’ll always know exactly what has to be done.
  • Start your task right when you get to your desk: Instead of surfing the web in the morning, jump right into the task at hand. Once it’s completed, start your next task, or walk away if you’re done. The key is to always have a purpose.
  • Use long lunches as a treat, not the norm: It’s amazing how much you can get done (in addition to eating) with that extra hour. Plus when you decide to use it, it turns into a treat.
  • Blow out the midnight oil: Since the team doesn’t work at night, everyone is fresh when they arrive at work each day. Burnout doesn’t exist when you have set hours that are actually respected by everyone.
  • And do what you got to do: Childcare duties, doctor’s appointments, and other to-dos can help you pause throughout the day. Funny enough, taking care of the necessities helps you focus even more when you’re at work.

Not all Winnie employees are parents, but the flexibility is a huge plus for the team and is also a selling point for potential candidates. “We set up that culture, and the people we attract really want that.”

Could Sara and Anne have started a company without being parents? Probably. But there’s something about the fierceness of parenthood that powers the fierceness of entrepreneur-hood. By drawing on their experiences, Sara and Anne have been able to knit together the two parts of their lives while creating a workplace that allows their team to do so too. The coolest part? All that extraordinary energy comes from one extraordinarily difficult phase of adulting. “Being a mom is my superpower,” says Sara. “I just don’t mess around.”  

About Kira Deutch

Kira Deutch is on the content team at Gusto, where she focuses on telling stories that empower small businesses across the country. She has a background in publishing and content marketing for startups. You can get in touch with Kira here.