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June 4, 2019

Lead(H)er: Stephanie Choi, Co Founder and COO at Sawyer

Everything you could ever want to do or find out is online, in an app, and available with just a click—or so Stephanie Choi once thought.

When Choi decided to sign her daughter up for early childhood education activities, like music classes to help with language development or gym classes to work on motor skills, there wasn’t an app for any of that—just outdated mom blogs and pages of Google search results. And when she did find a class? She had to print out and turn in a paper enrollment form.

“It was a piece of the Internet that hadn’t been worked on yet,” Choi said. “Nobody had brought technology into the space.”

At the time, Choi was working on inventory planning and growth at Rent the Runway. If she could figure out how to get a dress to a customer in a matter of hours, she knew she could figure out how to consolidate class listings and make it easier for parents to enroll their children. Her colleagues Marissa Evans Alden and Andrew Fernandez were equally intrigued by the idea. They soon left Rent the Runway to start Sawyer, which provides registration software for activity providers and consolidates those activities into one easy-to-use marketplace for parents.

The move into entrepreneurship was a natural one for Choi. She had always been interested in business and entered a training program at Macy’s after graduating from the University of Oregon with a bachelor’s degree in business. As the retail industry consolidated, she moved on to merchandise inventory planning at Bloomingdales.

“I loved what I did, but I was also really interested in what was happening in e-commerce,” Choi explained. “Department stores were not innovative places where you were going to find what was happening on the Internet.”

Rent the Runway, meanwhile, was in its early stages, and Choi joined the inventory planning department about a year and a half after the company launched. The experience taught her about what it takes to build a business, and eventually, Choi began to take on a more cross-functional role.

“It was a nice transition phase between the department store world and creating a startup from day one,” Choi said.

While Choi enjoys the early stages of business development, she’s now focused on a new challenge: how to grow the company she co-founded without losing sight of its identity.

Sawyer is currently available in New York and Los Angeles, with a beta running in Chicago, and the team is looking forward to expanding to more cities soon. They’re also working to build the consumer side of their dual marketplace, which is currently focused primarily on giving activity providers the software and support they need to get online and get found in the first place.

Some startups entering this scaling-up phase may find themselves struggling to hold onto core values, but for Choi and her team, those values have always taken center stage.

Once per month, the team hands out awards to members who have exhibited core values like “embracing yes—always” and “solve for tomorrow.”

“That’s been a big part of workplace culture and something we felt really strongly about defining as a team,” Choi said.

Thanks to that prioritization, Sawyer is poised to continue growing in line with what its founders originally set out to accomplish.

“What’s been really fun as the business gets bigger is that the challenges change for myself and my co-founders,” Choi said. “Today, it’s really thinking about the next phase of growth and how we keep the foot on the gas.”

Stephanie Choi family


Quick Q(uestions) and A(nswers)

What do you enjoy doing in your free time?

I have two kids, so most of my free time is spent with them and my husband. We like to explore different parts of the city and get outside to do different things. I also really love to travel, so whenever we can get away, we love seeing new parts of the world.

How do you handle stress?

I make a lot of lists. I still do like using a paper notebook so that I can cross things off. Digital solutions are great, but there’s something satisfying about crossing something off. I also like exercise and running when I have time. That clears my head and just works wonders.

How many cups of coffee do you drink in a day?

I’m from the Northwest, so coffee is in my DNA. I have two to three cups in a day – one before I leave the house and at least one when I get to the office for sure.

What’s one of your favorite places in the NYC area?

I love Brooklyn. It’s where I live and where I work. In the summer, we really like going out to the Rockaways and going to the beach. It’s amazing that there are these awesome beaches right in New York City.

What do you consider one of your greatest accomplishments so far?

I’m proud of the business that we built and our integrity, values, and approach. We always try to do right by our customers, and that has continued to be part of the business. I’m proud of the point that we’re at and the way that we’ve done it. We did core values early in the business, and I think the way we live in them every day is a special thing.

How does where you are right now compare to where you thought you might end up 10 years ago?

I didn’t necessarily see myself in this spot. Ten years ago, I was still at Bloomingdales, which is a very different business. I was just very open to what the possibilities could be. I’m happy with where I am, but I got here because things sort of came together and led to it, and I decided to say yes to things.

What’s your advice for recent college graduates?

Be open to a lot of different experiences. Some people have a clear idea of what they want when they come out of college, but being open to different opportunities and experiences can help bring you to a place that you didn’t even know existed.


Samantha Costanzo Carleton is a Contributor to VentureFizz. You can follow her on Twitter @smcstnz