Episode Overview

In this episode of Between Two COOs, host Michael Koenig interviews Jon Mark, COO of Vestwell, a leading provider of digital platforms for workplace savings and investment programs. Vestwell supports nearly 25,000 small businesses, over a million savers, and $25 billion in assets under management across all 50 states.

They discuss Vestwell’s mission to close the savings gap, its innovative approach to financial wellness, and Jon’s career journey from Bridgewater to COO at Vestwell.

Key Topics Covered

1. Vestwell’s Vision and Product Offerings

• Simplifying workplace savings through innovative digital platforms.

• Expanding beyond 401(k)s to include student debt paydown, 529 education savings, and more.

• Recent acquisition of Gratifi from Morgan Stanley to help employers support student loan repayment.

2. The Retirement Crisis

• Addressing the lack of sufficient retirement savings in the U.S.

• The role of state-sponsored retirement programs and employer-provided plans.

• Larry Fink’s warning about the coming retirement flood.

3. AI in Financial Wellness

• Vestwell’s integration of AI to enhance user experiences, including a new AI chatbot.

• Using AI to simplify complex financial concepts and empower financial advisors.

4. Jon Mark’s Career Path

• Transition from VP of Strategy to COO at Vestwell.

• Mentorship, curiosity, and deep problem-solving as key drivers of career progression.

• Lessons learned from working at Bridgewater and applying them to operations at Vestwell.

5. Navigating Risk and Strategy

• Managing risk by tying decisions to money, time, and outcomes.

• Balancing mission and growth by focusing on small and medium-sized businesses.

• Using a “chassis” approach to consolidate financial tools for broader impact.

6. Operational Challenges in a Regulated Industry

• Overcoming complex regulatory requirements.

• How Vestwell builds scalable, efficient processes within strict constraints.

7. The Role of the COO

• A COO’s need to handle diverse domains—engineering, HR, healthcare, and more.

• Strategies for managing imposter syndrome and fostering collaboration.

• Building a transparent culture through metrics and regular communication.

8. Mission-Driven Decision Making

• How Vestwell aligns its strategy with its mission to close the savings gap.

• Clear objectives, OKRs, and open communication as tools to drive alignment.

Memorable Moments

• Jon’s story about solving three major operational issues in one night before an acquisition deal closed.

• Insights on how Vestwell is innovating in financial wellness while maintaining a mission-oriented approach.

Key Quotes

• “You can’t just approach problems with jargon—you need to deeply understand the substance.”

• “Having a tangible North Star is critical. For us, it’s funded accounts—it’s the metric that matters most.”

• “At the end of the day, strategy and tactics are just bets with different time horizons.”

About the Host

Michael Koenig is the host of Between Two COOs, a podcast that dives into the stories, strategies, and advice of today’s top Chief Operating Officers. Learn more at betweentwocoos.com.