In this insightful episode of Between Two COOs, host Michael Koenig sits down with Jon Mark, the COO of Vestwell, a trailblazing digital platform revolutionizing workplace savings and investment programs. Vestwell is on a mission to close the savings gap in the U.S., serving 25,000 small businesses and managing over $25 billion in assets. Jon discusses how Vestwell simplifies savings plans for small and medium-sized businesses, including offerings like 401(k)s, 529 education savings plans, and student debt repayment tools. He shares how Vestwell leverages AI to enhance user experiences and support financial advisors, and he highlights the company’s commitment to making retirement planning accessible to all Americans. Jon also provides a behind-the-scenes look at his transition from VP of Strategy to COO, his problem-solving approach in a highly regulated industry, and his strategies for navigating risk and aligning operational goals with mission-driven objectives. This episode dives deep into the role of the COO, offering valuable lessons on leadership, career growth, and building scalable operations while staying true to a company’s purpose. Whether you’re a COO, an aspiring leader, or just curious about how innovative companies like Vestwell are reshaping financial wellness, this episode is packed with actionable insights and inspiring stories.