Source: Fortune
Summary
Kelly Esten, CMO and COO of Toast, has held both titles for over nine years, overseeing product launches, partnerships, and business growth. She has shifted responsibilities, delegating tasks and focusing on strategic oversight. Esten emphasizes the importance of sharing context with teams to empower decision-making. She sends weekly updates to marketing and enterprise teams to reduce dependency on her direct involvement. Esten says the COO role now dominates her focus, and she prioritizes where her time and energy go. She believes in giving teams authority but only when they have enough context to act independently.
Our Reading
The numbers tell one story.
Esten holds two C-suite roles at Toast.
She delegates and focuses on strategy over execution.
She sends weekly updates to keep teams informed.
She believes in empowering teams with context.
Author: Evan Null
Leadership Through Delegation
Kelly Esten has built a career at Toast by taking on multiple C-suite roles. Her leadership style is defined by the ability to let go of certain responsibilities. This approach allows her to focus on broader strategic goals rather than getting bogged down in day-to-day tasks.
Strategic Shifts in Role
Over nine years, Esten has transitioned from product marketing to operations. This evolution has required her to rethink how she manages her time and energy. She now prioritizes where her input is most needed, ensuring she doesn’t become a bottleneck.
Communication as a Tool
Esten uses weekly updates to share insights and priorities with her teams. This practice ensures that teams have the context they need to make decisions without constant oversight. It also helps maintain alignment across different departments.
Empowerment Through Context
She believes that giving teams authority is only effective if they have enough information to act. This philosophy has led her to be more deliberate in how she shares knowledge, especially as she manages more senior leaders and executives.
Future of C-Suite Roles
Esten sees AI as a force that could further blur the lines between C-suite functions. As roles become more interconnected, leaders like her will need to adapt their strategies to manage multiple responsibilities effectively.









