The assignment was meant to last three months. Kelly Sennatt Esten had started at UBS after college, entering through a rotation program that moved her among sales, finance, and strategy. Then came a chance to work in Switzerland. Three months became four and a half years in Zurich and London, an accidental European chapter that taught her something more durable than any title: before deciding what to say, notice the room.
She has described the habit as listening first. Living and working across cultures made her slow down, read context, and attend to the people around her. Today, that lesson travels between two jobs at Toast. Esten is the restaurant-technology company's Chief Marketing Officer and its Chief Operating Officer of Enterprise. One role shapes what Toast promises. The other follows how that promise survives sales, product, onboarding, and support.
Her shorthand is brisk: “Go fast and stay close to the customer.” The interesting word is not fast. Plenty of companies move quickly. It is close. Esten's career has been a repeated effort to shorten the distance between the person making the message and the person trying to run a business through a lunch rush.
01 / Learning the room
The internship she expected to dislike
Sales grabbed her before marketing did. At her father's urging, Esten took a college internship selling municipal bonds. She went in skeptical and came out captivated by the energy of the floor, the pace, and days spent talking with customers. After Dartmouth, UBS hired her full time. The rotation program gave her several angles on the bank, and Europe enlarged the frame.
Her undergraduate path had pointed somewhere else. Esten competed nationally in squash and chose Dartmouth in part for the sport. She studied environmental earth sciences and French, completed field study in Belize, and won the department's Upham Award for senior research. The combination is useful in retrospect: fieldwork rewards observation, and sales rewards attention. Both begin with what is actually happening, not what a plan says should be happening.
Tuck brought her home in more than one sense. Hanover was familiar. The close campus made accountability personal. She co-chaired the Entrepreneurship Club, helped lead Tuck Women's Hockey, and met Jordan Esten, her future husband, at orientation. She had one highly practical qualification for hockey: “I could skate backwards, so I was a hot ticket,” she joked in a Dartmouth alumni profile. Her team won the league.
A spring-break trip to China offered another telling scene. Professor Peter Golder spent the flight home preparing her for an internship interview. She got the role at Boston clean-energy company EnerNOC, then joined full time after graduating in 2012. Over six years, she built product marketing, worked on the go-to-market strategy for energy-intelligence software, and led enterprise sales. The move back into sales would later become, in her account, the essential stop on the route to CMO.
Clarity of thought is a big lesson I've carried with me.Kelly Esten, on what sales taught her
02 / Do no harm
A growing company with mismatched carpet
Esten arrived at Toast in 2017. The office sat in an incubator near Fenway Park. Desks had colonized the available space, the decor was improvised, and the carpet did not match. More important, restaurants were already buying the product. Her first mental instruction was “do no harm.” Learn what was working. Build on the early success. Do not mistake arrival for a mandate to rearrange everything.
She had found the company through someone she knew, but the category felt personal. Her father had worked restaurant jobs through high school and helped put himself through college at an Italian restaurant and a men's store. Esten had done summer hospitality work herself. Restaurant technology made a complicated B2B product legible because she understood the customer and cared about the setting. She also loved food and going out to eat, a modest but important source of conviction.
Toast's marketing team was roughly a dozen people when she joined. By 2024, it had grown beyond 200. Her own remit expanded too: product and partner marketing, pricing, market insights, partnerships, enterprise leadership, and eventually the CMO role. The through-line was not a channel or a campaign. It was the insistence that restaurants remain the protagonists.
“It's much more impactful and authentic when a restaurant can say, ‘Hey, here's how I'm using Toast, and here's my story,’ than what we can say,” she told Entrepreneur. The approach sounds obvious until one considers how often B2B marketing turns the customer's actual work into a decorative testimonial. Esten's version gives the operator the microphone and asks the technology to stay in a supporting role.
03 / The shutdown test
When proximity had to produce speed
In early 2020, Esten had just overseen a new line of point-of-service products when dining rooms stopped. From home, while she and her husband traded childcare shifts and their toddler occasionally entered a video call, she organized the fastest product launch of her career. Toast Now offered digital ordering, delivery, and digital gift cards to restaurants, including businesses that were not already Toast customers.
The work sat alongside Rally for Restaurants, a campaign that directed diners toward restaurant gift cards. The practical need was brutal and immediate. Esten knew operators personally, including a high school friend who had recently opened a restaurant outside Boston. In the line she gave Dartmouth, the scale of the crisis became individual: “Most of our clients are independent restaurants. They're someone's dream.”
Listen closely enough to identify the real constraint. Move quickly enough to matter. Let the people doing the work explain whether the solution helped.
Toast Now also demonstrated the organizational value of building with customers. Esten later called it one of the company's most significant launches and pointed to a companion video about how customers shaped the product. The lesson was not simply that listening is kind. Listening can be a form of product velocity because it cuts through imagined problems.
Her customer frame includes three people: the operator, the restaurant employee, and the guest. Each touches the same system with different needs. “The employee can't deliver a great guest experience if they don't have the tools they need,” she said on the Give an Ovation podcast. The operator needs a coherent view of the business. The guest wants hospitality without friction. Good restaurant technology has to respect all three at once.
In these moments, your regulars matter the most.Kelly Esten, on restaurant guest relationships
04 / Owning the seam
Two titles, one customer journey
The dual CMO and COO of Enterprise role makes that three-sided model an executive responsibility. Toast's enterprise customers bring more locations, layers, integrations, and handoffs. Esten has said the segment needed someone to pull the thread across the full journey, from sales and product to onboarding and support. The work puts her near operational detail, then sends her back to marketing with fewer abstractions.
There is productive tension in the arrangement. Marketing and operations keep different rhythms. One creates attention and expectation. The other manages delivery and exceptions. Esten told the Fortune COO Summit audience that running both is a balancing act, connected by keeping customers in the center of the frame. Her concise version is more portable: assign someone to the seam where a promise becomes a handoff.
Recent work makes the pattern visible. She has convened customer advisory boards where restaurant leaders critique products and roadmaps, argued for technology that protects simplicity as businesses scale, and spoken about AI as another wave of restaurant change. Her interest is practical: partners integrating faster, operators getting answers sooner, and teams preserving hospitality while systems handle more complexity.
Community sits beside the operating model. Esten joined the board of the Culinary Careers Program, which prepares high school students for culinary careers. She has also highlighted Toast's fundraising tools and the company's support for hunger-focused organizations. On LinkedIn, her updates routinely return to advisory-board members, restaurant teams, and the people behind growing brands. The executive is present, but the post usually points the spotlight elsewhere.
The small details keep the portrait from hardening into a management diagram. Esten still likes the outdoors in bad weather. She once balanced career risk with her husband by treating their household like a portfolio. Her official Toast biography answers “favorite toast” with a cinnamon-raisin English muffin. She is direct about loving restaurant stories because she loves restaurants. None of this is a grand theory. Together, it explains why closeness is credible as more than a slogan.
A marketer can learn the language of a category from research. An operator learns where the promises break. Esten has spent her career moving between those perspectives: from a sales floor to an earth-science field study, from Zurich to Hanover, from energy software to restaurant software, from marketing into enterprise operations and back again. Each move added context. The job now is to keep that context intact as Toast grows.
Speed will always photograph better. Closeness is quieter. It looks like an operator asking another question, a leader leaving room for a team's judgment, or an executive getting back on the road because the customer-facing part of the work remains her favorite. The table, in Esten's story, is not a metaphor invented after the fact. It is where the work keeps returning.