Introduction

Kelly Esten’s dual leadership role at Toast represents a growing trend among C-suite executives who must balance strategic vision with operational execution. After nearly a decade at the restaurant technology company, Esten now serves as both chief marketing officer and chief operating officer, a combination that forces a reevaluation of how time, energy, and authority are distributed across an organization.

What Happened

Esten’s ascent to holding both the CMO and COO titles was not instantaneous. Over nine years, she led product launches, forged key partnerships, and helped scale Toast’s presence with larger restaurant groups. The dual appointment required her to consciously decide which remnants of her previous roles to relinquish and which responsibilities to delegate. She now focuses on strategic supervision rather than day-to-day execution, allowing her to direct energy toward higher-impact organizational goals.

Why This Matters

Combining marketing and operations under one leader creates a unique lens on how a company connects with customers and runs its internal processes. Esten’s approach highlights a critical tension: when one person oversees both functions, decisions in one area can directly impact the other. Her experience offers a case study in how C-suite leaders can restructure their authority to prevent bottlenecks, encourage team autonomy, and maintain strategic alignment without micromanaging every detail.

Key Takeaways

  • Leadership effectiveness increases when leaders deliberately offload tasks rather than hoard them.
  • Providing teams with sufficient context is essential for autonomy to work.
  • Regular communication, such as Esten’s weekly updates to marketing and enterprise teams, bridges gaps without requiring constant oversight.
  • Setting a higher threshold for involvement helps prevent leaders from becoming the single point of failure.
  • AI and automation may further blur the lines between marketing and operations, making this dual-role model increasingly relevant.

Conclusion

Kelly Esten’s dual CMO and COO role at Toast illustrates that holding two strategic titles is less about doing more work and more about redefining how work gets done. By consciously delegating, sharing context, and setting clear boundaries, she demonstrates a model for modern executives who must navigate competing demands while keeping their organizations agile and responsive.