Colleen Miller: Rocket Ship to Rooted
- Brick + Tides
- Nov 19
- 7 min read
Updated: 5 days ago
The wind was moving that afternoon in Biddeford, sharp enough to lift the last of October’s leaves and send them tapping against the tall windows of The Lincoln. Downstairs, the team at Batson River had started to hang Christmas lights, strings of gold flickering over the clink of glassware. Every terminal in sight ran on Toast. At Batson River, at Spinning Jenny’s, even in the cafe where we sat, the same platform powered orders, payments, takeout, and delivery.
Colleen smiled when she noticed. The platform she spent more than seven years building was right there on the counter, part of the everyday restaurant rhythm she once worked to steer. “That was the definition of a rocket ship,” she said. “My years there were the most formative of my career. The speed of product development and the rapid evolution of the company really pushed me to grow as a leader.”
Today she lives in Kennebunk, Maine, a place she calls calm, balanced, and just the right distance from Boston. “It could take you an hour and a half to drive seven miles in Boston,” she laughed. “Here, it is calm. I still love the work. I just love doing it from here.”
The Ride
Miller grew up in Brighton, Massachusetts, and stayed local for school at Boston Latin and then Boston College. Her career started at Harvard Business Publishing, just as e-commerce was beginning to hum.
“At the time, leadership was beginning to build the first website for Harvard Business Review and case studies, and they were looking for volunteers,” she said. “I raised my hand. I wanted to learn everything. I ended up convincing HBS professors to put their IP online for the first time, becoming a HTML developer coding the intranet, and learning everything about web development there.”
That single decision set her on a three decade climb through digital commerce. At Upromise, she built an online shopping portal with 800 partners to help families save for college. At Staples, she managed a $6B B2B business. Each step carried her closer to the intersection of technology and everyday life, the kind of work that changes how people shop, order, and connect.
Then came Toast.
“I was the first product leader the founding team brought in during Series B, so they were early in their journey,” she said. “None of us had any idea whether it was going to work, but we all felt this magic happening, and a strong belief in the idea. We were obsessed with solving customers' problems and tackling the issues they faced with their current technology.”
When she joined, Toast had about $15M in annual recurring revenue. By the time she left, ARR had passed $1.3B. The company grew from 20,000 restaurants to more than 140,000 locations worldwide.
She remembers the blur of those early days, testing, breaking, rebuilding, and the discipline that followed once the company went public. “Scrappy startup, you go fast, you test, you break things, you learn,” she said. “You are trying to find product market fit.”
By year seven, the rhythm was different. “You have more products, it takes longer to make decisions, and a lot more people are involved. You are a public company now. You have far more rigor around compliance and regulatory needs. You have to make sure that every release prioritizes quality. You cannot afford to push out a release that causes restaurants to go down or introduces a bug right before dinner service.”
She paused for a moment “The people are what make that company so great,” she said. “They are incredibly smart and customer centric, and you can see what they have done for restaurants by consolidating many different vendors into a single platform that now fuels a significant share of the US market.”
Behind those billions are countless moments of hospitality happening in real time. Tickets route correctly, payments clear, devices stay in sync, and teams keep moving. Her product leadership is not a trace in that system. It is one of the reasons it works the way it does.
Opening Doors
Within Toast’s rapid climb, Miller carried out another mission. “I was also the first female leader in R&D and needed to scale the product and design orgs” she said. “I hired more than fifty team members during my time there, many of whom were women and many of whom are still there today.”
She was determined to make sure their voices were heard. “It has always mattered to me to balance the conversation and the perspectives in the room,” she said.
That commitment did not end when she left the company. Colleen recently partnered with several organizations including LiftUp Connections, VentureFizz, and Label Sessions to build programs for women in tech who are navigating career pivots and AI transformation. “It has been deeply fulfilling to mentor and support women as they move through difficult stretches at work. I have lived through those chapters myself in environments defined by rapid innovation and fast scaling. Being a steady voice, a sounding board, and an advisor in those moments is meaningful to me.”
The mentorship runs both ways. Former Toast colleagues stay connected across time zones, sharing clients and lessons from intense years of growth. “There is a group of people who used to work at Toast who now work in these fractional capacities,” she said, describing product, sales and go to market advisors who help startups scale. “A new network of seasoned leaders is forming as people build their own consulting and advisory businesses.”
The Next Chapter
Through Kennebunk Product Ventures, the company she founded last year, Miller advises startups and private equity firms on product diligence, product strategy, organizational design, and AI transformation. “This next chapter of my career has been more about balance,” she said. “I love the work itself, whether it is shaping product strategy, digging into design details, finding real product market fit, or guiding an investment firm through a turnaround. But I can also take a walk by the ocean in the middle of the day.”
Colleen recently joined the board of Grateful Giving, a nonprofit micro-donation platform. “It is a perfect blend of my Commerce experiences, building a micro donation platform where every purchase can do good. I am helping them design the right user experience,” she said. “I am their first hire in Maine.”
AI has become her latest focus. “Big AI nerd,” she said, laughing. “Companies are struggling because there is pressure to ‘just do something’ with AI. Some people are checking a box and creating a report or a support agent without thinking about how to transform workflows or how to give time back to time strapped users. I help clients understand the most transformative use cases and move their workflows into automated systems of action”
Advice for Maine Restaurants
When the conversation shifted to Maine’s restaurant scene, the one Toast helped modernize, Miller’s answers felt like mentorship for every Main Street business owner.
“There are great restaurants that do not offer takeout or delivery, or do not have a website,” she said. “In Maine, many restaurants use Facebook pages, which only reach certain groups. Younger people are living and working in Maine, and they are not going on Facebook to look at menus.”
She pointed to the tools already available. “Platforms like Toast have website generators that handle this in a few clicks and integrate with Google,” she said. “A lot of small business owners get into hospitality because they love making great food and serving guests. They are not always tech forward. Platforms that take these tasks off their plate are incredibly helpful and help drive additional revenue.”
Then she leaned forward, talking about the future. “Agentic commerce is going to be the next wave,” she said. “How do you find restaurants through ChatGPT? You already see that when you search for something, you often read the answer at the top instead of going into the results. So how will restaurants be discovered inside chat based AI agents?”
She smiled again at the idea. “I want to say, I would like to order a cheese pizza on ChatGPT, and it should tell me the three restaurants near me that deliver and the three that offer pickup. Then I can choose.”
That is the future she is helping shape, a world where a Maine chef’s menu appears inside a digital conversation halfway around the globe.
Passing It On
As Miller talked about Maine’s growing tech scene, her enthusiasm turned to the people behind it, the next wave of doers and dreamers she now supports from Kennebunk. Her career may have been built in Boston, but her energy today belongs to Maine.
She encourages young Mainers to adopt the same bias toward action, stepping into opportunities even when the way forward is still developing, a trait that matters in any growing innovation hub.
She has connected with a growing circle of innovators through NexusMaine.com, founded by George Matelich and Jimmy Haight, as well as the Northeastern Roux Institute, StartUp Maine and Maine Tech Week. She credits these groups for building momentum and creating bridges between local founders, remote professionals, and students who once believed they had to leave Maine to work in tech.
Her story makes the case that they don’t. Maine, she believes, is ready for its version of rocket ships.
Maine, Finally
When the conversation turned from work to life, her expression softened. “Maine was always our happy place,” she said. For years she and her fiance, Jason, drove north on weekends. “We loved bar hopping in Portland, going to the beach, taking a boat ride in Camden, and hiking in Acadia. Every time we came up, we tried to explore somewhere different, and we loved it every time.”
The move took courage. “Even the transition was a little scary. I am a city person and I still need to be able to walk to something. You need to be able to walk to get coffee,” she said. “But we found the right happy medium.”
Her favorite places are close to home now. “Parsons Beach in Kennebunk is a hidden gem,” she said. “Love Mother’s Beach, love walking there. We like the Saco Heath Preserve. It is a fun walk with a colorful boardwalk.”
Worth the Ride
The light in The Lincoln shifted as the sun dipped lower, bright across the brass railing of the mezzanine. Downstairs, a barista wiped the counter beside a Toast terminal, a small reminder of the care Miller’s teams put into every feature so restaurant staff could breathe a little easier during a busy day.
She didn't point it out, but it was impossible not to notice. Those screens and that product will follow her for the rest of her life. They are symbols of a company that changed an industry and of a woman who helped steer it.
She looked out the window as another guest moved through the leaves. She breathed in the quiet. The work still mattered, but doing it from this place felt like exhaling after a long hike, the kind of calm you only earn by making the climb.