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Toast's Kelly Esten Balances Dual C-Suite Roles as CMO and COO
ReToast's Kelly Esten Balances Dual C-Suite Roles as CMO and COO
Kelly Esten has served as both chief marketing officer and chief operating officer at restaurant technology company Toast for nine years, developing a leadership approach centered on delegation, written communication, and knowing when to step back from day-to-day execution.
Kelly Esten holds two of the most demanding roles at restaurant technology company Toast, serving simultaneously as chief marketing officer and chief operating officer. Over nine years at the digital ordering and payments firm, she has run product launches, led partnerships, and helped grow the company's business with larger restaurant groups. The dual title spans marketing and operations, pushing her to think about the business as a whole rather than through the lens of a single function.
Making room for that expanded remit has required Esten to regularly decide which parts of her former jobs should no longer be hers and which tasks to hand off. «I get to supervise, but I don't get to do the work anymore,» she said. With two C-suite roles, she acknowledges that the operator side «certainly dominates,» making her increasingly deliberate about where she invests her «time and, more importantly, energy and attention.»
Her threshold for diving into details has risen accordingly. Esten still weighs in on work she once owned, but she tries to reserve that involvement for moments when she believes her opinion could genuinely change a business outcome. If decisions routinely depend on her input, she treats that as a signal that her team needs more authority to make those calls independently. Otherwise, she becomes the bottleneck.
Delegating authority only works when people have enough context to use it well. As Esten moved from managing managers to overseeing executives, she became more intentional about sharing information so teams could make decisions without waiting for her. She first recognized the need while running product marketing, when leadership decisions and discussions did not always reach her team and her team's insights did not always make their way back up the chain.
To close that gap, Esten began writing weekly updates describing what she was thinking about, working on, and prioritizing. She still sends two every week, one to marketing and another to the enterprise organization, giving both teams more of the information they need to operate without her direct involvement.
Esten discussed her approach in the latest episode of Fortune Next to Lead, where she reflected on what she has learned from moving between marketing and operations, how holding both roles shapes the way she runs them, and why artificial intelligence could further blur the lines between functions across the C-suite. She also addressed what that shift means for leaders who take on more than one remit.
Her experience illustrates a broader challenge facing executives at growing technology companies, where overlapping responsibilities and lean leadership structures increasingly require top managers to supervise work they once performed themselves. For Esten, the answer has been a deliberate combination of delegation, structured communication, and a higher bar for personal involvement in day-to-day decisions.
