July 26, 2017

Lead(H)er: Margaret McKenna, Co-Founder and CTO at Pepperlane

“At one point in my career, I ended up at a temp job and I was really bored. When I noticed they were using a basic programing language to do a lot of their automation, I spent my days figuring out how it worked,” explains Margaret McKenna, Co-Founder and CTO at Pepperlane.

“I quickly realized that I loved programming and wondered how I didn’t know about it my whole life!”

Ever since she was a little kid, Margaret wanted to be a writer. When it was time for college, she left her family home in western Massachusetts and went to study English and creative writing at Columbia.

“After graduation, I decided that Montana would be a great place to be a writer. I moved there and I wrote book reviews and short stories. After a while, I realized I needed health insurance and I wasn’t making any money, so I moved back east to Boston.”

Margaret fell in love with programming shortly after she returned home. Although she thought her temp job was boring, she became very interested in their use of automated tasks. In order to learn more, she befriended engineers and bought a bunch of programming books.

“After my temp job, I got a job in store planning at Talbots’ corporate headquarters and started automating everything I could get my hands on. The next place I went to was a startup called ChoiceStream where I again tried to sit with and learn from every engineer I could. I was very fortunate because people there were really generous with their time and expertise.”

While at the startup, Margaret picked up five coding languages and learned from her peers.

“This was in the mid-2000s, before the rise of online coding classes. When I first started learning, Google was around and there were forums for coding, but it was really old school. I’d just go buy programming books at Barnes & Noble and teach myself.”

After she felt she had learned as much as she could at ChoiceStream, Margaret left the startup. She wanted to travel and do something new with her technology experience so she moved to Ghana for six months.

“Once I got there, I started hanging out at this internet cafe. I met a bunch of local entrepreneurs and one of them was working on wireless mesh networks for rural areas. Basically, you could supply internet access to a whole community with a single internet connection by pinging that connection around the community. I spent my time working on that project, applying to grad school and trying to figure out if I wanted to go to business school or do something more technology related.”

Margaret decided to return home and to enroll at NYU’s ITP (Interactive Telecommunications Program).

“It’s kind of like the Media Lab in that it’s a mix of arts and technology. So there were people in my class who were professional dancers and painters and there were others from software and hardware engineering backgrounds. They kind of just threw us all together and had us figure out interesting things to do. It was really fun. I spent most of my time focused on data and data visualization during that time”

During her time at NYU, Margaret realized she wanted to work on consumer-facing technologies. There was a lot happening in the New York startup world and she was very excited to be a part of it.

“New York was an exciting time then. The founder of FourSquare went to ITP and the first version of FourSquare was developed there. I felt really tapped into the startup world and I was excited about what was happening.”

Shortly after Margaret graduated, however, her wife got a job at Harvard so they moved back to Boston. Margaret soon realized that one of her favorite apps, Runkeeper, was headquartered in downtown Boston so she sent them a note asking if they needed any software engineers. She was hired shortly afterward.

“When I started, I focused on the iOS app and the back end. I soon realized Runkeeper had this amazing amount of data about running and I proposed that we split off a team to analyze that data. I started the data team at Runkeeper. It was really exciting for the business to get these insights and we started to think about how we would introduce personalization into the app based on this accumulated data.”

Over time Margaret also led the Platforms Engineering team at Runkeeper, which included DevOps, back-end engineering, and data infrastructure and analytics. “I worked with an amazing team with diverse talents, and I learned a ton from and with them about managing infrastructure and software at the scale of 50 million users.”

After Runkeeper was acquired by ASICS last spring, Margaret felt she was ready to explore starting a company.  She connected with Jess Petersen who told her about a new company she was starting with Sharon Kan. Pepperlane was a great match for both her technical interests and skills and her desire to do work that helps others.

“I joined them last summer! We’re building a software platform and community to help mothers start and grow their small businesses. Instead of trying to get back into the workforce, we help women figure out how to do build their own business by pursuing the skills and the passions that they already have, on their own terms. We launched this past spring, and it’s been very inspiring to see all the amazingly talented women who have joined our platform.”

Pepperlane team doing some weeding on the banks of the Charles at a TUGG volunteer day.
Pepperlane team doing some weeding on the banks of the Charles at a TUGG volunteer day.

BS: How do you manage stress?

MM: I go for a run, and then I make a plan. Usually, when I’m stressed, it’s because there are a million things going on and I need to focus, so making a list helps.

BS: How many cups of coffee do you drink a day?

MM: Uh four… probably. All before 6am. My son gets up really early so the only quiet time I have is between 5 and 6:15am.

BS: What do you like to do in your free time?

MM: I like to play with my son, read books and go for hikes. I like to hike in the White Mountains but that’s been harder to do since I had my son. We’re starting to try with shorter hikes though!

Margaret McKenna hiking with her son
Margaret hiking with her son

BS: Where is your favorite spot in Boston?

MM: I have to admit I don’t cross the river very much now that I don’t work at Runkeeper anymore. I live in Cambridge, and Pepperlane works out of Accomplice’s offices near Lechmere, so my most common Boston outing is riding my bike to work. I take my son to daycare in a bike trailer, and then I ride along the river bike path to work. It’s a very beautiful ride, and a great way to start and end the day.

BS: If you had to choose one thing, what would you say is your greatest accomplishment?

MM: Having a happy family!

BS: Ten years ago, is this where you would have seen yourself?

MM: No, but I’d be psyched if I knew this was coming! Ten years ago, I was getting interested in technology but I didn’t even know what a startup was. I liked what I was doing and I wanted to do more but I didn’t really know what path to take. There weren’t a lot of people like me around.

BS: What one piece of advice would you give to a recent college graduate?

MM: I found things that were interesting and exciting to me by finding things that were broken and solving them. Just find problems and fix them.

Brianne Shelley is a Contributor to VentureFizz and an Account Representative at BlueGrace Logistics. Follow Brianne on Twitter: @MuddleandMix.

Images courtesy of Margaret McKenna.