Kelly Esten has spent nine years at Toast building a rare kind of executive stack: chief marketing officer and chief operating officer at the same time. The restaurant technology company now relies on her to bridge marketing, product launches, partnerships, and operations across a business that serves digital ordering and payments.
Esten says holding both roles has forced her to become more selective about where she spends her time and energy. 'I get to supervise, but I don’t get to do the work anymore,' she says. That line captures the central challenge of modern management: when a leader keeps too many hands on the controls, the organization slows down.
Her operator role now dominates, and she says her threshold for getting into the details has risen. She still weighs in on work she once owned, but tries to do so only when her input can actually change the business outcome. If decisions always depend on her, she sees that as a sign she has become the bottleneck.
That is a problem in any large company, especially one where information has to move quickly across functions. Esten says she first saw the need for better communication while running product marketing, when leadership decisions did not always reach her team and team insights did not always reach leadership.
Her response was straightforward: weekly updates. She writes them to share what she is thinking about, working on, and prioritizing. She still sends two each week, one to marketing and one to the enterprise organization, so both teams have more information to operate without her direct involvement.
That is the quiet discipline behind real scale. Capital rewards clear rules, and organizations do too. When the chain of authority is clear, managers can make decisions faster, and the business stops paying the hidden tax of waiting for one person to sign off on everything.
The market has already voted for this model in countless companies: leaders who delegate well create more leverage than leaders who collect tasks. Esten’s approach shows that the highest-value work in a modern company is often not doing the job yourself, but building the system that lets other people do it well.
