Jennifer Zimmerman, 37

It’s tempting to call Jennifer Zimmerman a multi-hyphenate. First, there’s her full-time job: she works remotely in event sales. She’s mother to two young children. And then there’s her business — Heel Hoodie, a reusable shoe cover brand that’s attracted clientele nationwide.

How does she do it all? It’s a question she’s obviously been asked before. 

“I always say to everybody that you just have to turn off,” she says. “I did have a time where I was trying to do everything all the time and I would get frustrated. I was like, ‘This isn’t fun,’ and I want to enjoy this.” 

The idea that work is something to be enjoyed and not simply tolerated is a value imparted to Zimmerman by her mentor and father, a former scientist and professor at Dartmouth College. Despite his intelligence (Zimmerman calls him a “very, very smart man”), he always made you feel like his equal. And his passion for his research and teaching has stuck with her all these years later.

“I loved that he was so happy in what he was doing,” she says. “He just did all of these really amazing things and he loved it.” 

Zimmerman’s path to becoming a business owner was full of fits and starts. The idea for Heel Hoodie came to her in 2013 when she was traveling frequently for work and had to pack high heels. Instead of dirtying her clothes with shoe detritus or wrapping them with a plastic bag, she cut up socks and sewed them together as a shoe cover. Colleagues took note and suggested she sell them on Etsy.

Fast forward, and she’s a multimillion-dollar business owner, right? Wrong. It’s been a slow-going process of business tweaks on Zimmerman’s end. She really hit her stride at the start of the pandemic, when customers started requesting wearable shoe covers. Etsy records show her business went up 418% from 2019 to 2020. 

“It takes a lot of time, because it’s just back-and-forth,” Zimmerman says. “Everything’s just kind of progressed so slowly, and things take a long time. People want success overnight.” 

One person is missing as Zimmerman’s business fully blossoms — her father. He died unexpectedly shortly after her first Heel Hoodie event. Her success was one of the last things they talked about before he died. 

“He was always a huge supporter of me doing it,” she says. 

Name: Jennifer Zimmerman

Age: 37

City of Residence: Naples

Employer: Heel Hoodie

Title: Owner / Creator

Birthplace: Boston

Years in the area: 8

Marital Status/Children Married / 2 children (2.5 & 4)

Alma Mater/Degree: Bachelors in Events Management

What community group or organization are you most involved with? Currently I am the Service Project Coordinator for Moms Club of Naples

What's the weirdest job you've ever had? Giving event surveys out at the Bass Master Classic in Chicago

What's your top tip for being productive?

Make sure to make time for yourself and your family. Otherwise all the work you're doing becomes stressful and if you're not having fun with what you’re doing, you will resent your work — which is no good.

If you could have a side hustle, what would it be? Honestly, my business IS my side hustle. I also work full time for an events company during the week, and am a full time mommy to 2 toddlers. :)

What's your favorite off-hours activity? Being with my family outdoors

Have you gone to the movies in 2021? If yes, what did you see? With the little ones, it’s hard to get out. We love Netflix movies on the weekends and our current favorite is Vivo!

What's the top item on your bucket list? Run a marathon in a big city! I have done a half...so I’m halfway there! ;)

What's your favorite podcast? I love Football, and Kyle Brandt has an awesome podcast!

Where is your happy place? Maine

Describe yourself in three words: Trustworthy, Hardworking, Fun

Who is your mentor for your career and why? My Dad, he loved his job and never "worked" a day in his life.

What are the biggest lessons you have learned from your mentor? Love what you are doing, appreciate the people that got you there, and return the favor to others. Never forget where you started.