One executive, two titles

Kelly Esten holds both CMO and COO roles at Toast, the restaurant technology company. Over nine years, she has run product launches, led partnerships, and grown the business with major restaurant groups.

The operator role dominates

Esten says the COO side "certainly dominates," forcing her to be deliberate about where she spends her time, energy, and attention. She no longer does the work herself, only supervises it.

“I get to supervise, but I don't get to do the work anymore”

Know when to step in

Esten only weighs in on decisions when she believes her input could truly change the outcome. If her team routinely needs her approval, she sees that as a sign they need more authority to decide independently.

Share context, enable decisions

Esten sends two weekly updates, one to marketing and one to enterprise, sharing her priorities and thinking. This gives teams the context they need to make decisions without waiting for her direct involvement.

Information flows both ways

Esten started sharing weekly updates after noticing that leadership decisions didn't always reach her team, and her team's insights didn't always make it back up. Two-way communication became essential.

AI could blur C-suite lines further

Esten believes artificial intelligence could further blur the boundaries between marketing and operations roles across the C-suite, creating new challenges for leaders managing multiple functions.