“I think I’ve always been a problem solver. I love crossword puzzles and analytical types of tasks. Once I started working at Harvard Business Publishing, there were just so many great problems to solve and analytical challenges about building a new eCommerce business. My transition into the tech space was a little bit unusual, but it was being at the right place at the right time and falling in love with the work,” explained Colleen Miller, Senior Director of Product and UX at Toast.
Colleen grew up in Brighton and attended Boston College where she studied French and Psychology. She got her first job at Harvard Business Publishing working in Customer Service.
“This was back in ‘96 when people were trying to figure out eCommerce, how to transition content offline to online, monetizing the web and things like that. My boss at the time said, ‘Does someone want to work on this new website thing?’ and I happened to be in the right place at the right time. As a person who was interested in the web and what was happening there, I raised my hand. I ended up taking a project manager role and working to get the first version of Harvard Business Review and case studies online.”
“I think for me with HTML, it was just another language. You have to understand the syntax, you have to understand how things are formatted. You have to practice it. I think it was kind of a natural thing for me to pick it up pretty quickly. I stopped that piece after a while because I realized I could concentrate on what I was more effective at, driving things forward, being organized, having a plan and working with engineers to help them understand the business side.”
After eleven years at Harvard, Colleen decided to pursue her passion for eCommerce and user experience at Upromise.
“Upromise helps families save for college. I worked on a project to overhaul their online shopping experience. They have an online shopping portal where consumers can shop online and get a percent back in a college fund for their kids. I spent about four years there. I started out as a manager and ended up as a VP. I went through the ranks there and got some of my first management experience there with some great mentorship.”
Staying in the eCommerce industry, Colleen transitioned into a Product Lead role at Staples. She oversaw Staples Business Advantage, the B2B arm of Staples, where she had the opportunity to design and develop their mobile experience from the ground up.
“I worked in the Staples Velocity Lab in Kendall Square and had the opportunity to build out the team, hire the folks that I wanted and really start mobile first. I worked on their iOS, Android and mobile web applications there. Once I got mobile up and running, I transitioned to running the desktop eCommerce site.” After several years at Staples, Colleen read an article about the changing landscape of restaurant technology and what Toast was doing. “That’s when I reached out to one of my LinkedIn connections, Steve Fredette, who was one of the co-founders of Toast. He & I had worked together when I was at Upromise and he was at Endeca.”
Colleen was drawn to Toast because she found it to be the perfect blend of two things she loved - technology and restaurants. She was energized by the passion the leadership team showed when she met them in person and their enthusiasm for helping their restaurant customers succeed.
“They have some great stories about how they started in a basement with three or four guys and an idea. Then after spending a lot of time at different restaurants, they discovered they had greater pain points they could solve for them, and pivoted to another idea. I got very excited about the opportunity to lead a team there. It wasn’t just about the game-changing technology, it was also about being a partner to the restaurant and helping them grow their business. My product and design team is amazing. I’m very fortunate to be here,” Colleen smiled.
Colleen’s day to day at Toast is pretty diverse. She oversees a team of fifteen people in product and design. Her daily tasks can range from design reviews, discussions with large enterprise customers, new product research, quarterly roadmap planning or one on ones with her team members.
“We’re doubling the size of the team—we’re hiring like crazy. We’re also taking on more customers. In fact, more customers are knocking on the door than we can even get to right now, which is a really good problem to have! We’re working on some really exciting new products and projects on the software and hardware side. Lots more to come from Toast, keep an eye on us.”
Rapid Fire Questions
BS: How do you manage stress?
CM: I do hot yoga and that really helps. I sweat it all out!
BS: How many cups of coffee do you typically drink in a day?
CM: One… it might be a big one though.
BS: What do you like to do in your free time?
CM: I have two kids, they’re teenagers so they keep me pretty busy. I like to travel, and I like to exercise. I like to keep up with new technology so whether it’s going to meetups or talking to people in the community, just those types of things.
BS: Where is your favorite spot in the Boston area?
CM: Hmmm that’s a tough question. I was going to name a few Toast restaurants but I don’t want to leave anyone out! I love Portland, Maine. I think it’s a great town with all these great restaurants and breweries within walking distance. Always fun to visit for a weekend.
BS: If you had to choose one thing, what would you say is your greatest accomplishment other than family?
CM: I always pride myself on the teams that I’ve built. I think building teams that work well together and enjoy working together is a great accomplishment. When you’re hiring, it’s another type of puzzle. What skill set will add to the team, who will bring out the most in this team, what will make this team productive. Some of it is psychology. You really have to get to know the people, learn their strengths and adjust accordingly. I like to understand what makes them tick, learn how they like to get feedback, and their working style. Those are all soft skills that I feel like people overlook sometimes. People will ask me ‘Your team loves you! How do you do it?’ The answer is, don’t overlook team dynamics and their effect on results.
BS: Ten years ago, is this where you would have seen yourself?
CM: Probably ten years ago, yes. Probably twenty years ago, I was still thinking I’d be living in Paris somewhere. But once I got into the product side, I had always seen myself leading a team for a company that I was really excited about.
BS: What one piece of advice would you give to a recent college graduate?
CM: I think there are a couple of things that come to mind. One is to volunteer for opportunities that come up, things that are going to stretch you, things that you might not know anything about, but you’re interested in. I wouldn’t be in my position if I hadn’t done that. Also, be authentic. I think that’s something that has helped me throughout my career. I think that if you’re authentic, open and honest with the people you work with, that builds trust, and trust is an important part of any team. Working in a number of different companies in a male-dominated tech industry, you’re going to hear from lots of different people that you should try this, do this and be more like this person. Obviously, you take some of that feedback if it’s relevant and apply it. But bottom line is, just be true to yourself.
Images courtesy of Colleen Miller and Toast.