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.

In this episode of Between Two COOs, host Michael Koenig sits down with Valentin Gruber, COO of HomeToGo, to explore the inner workings of the vacation rental aggregator and its strategy. HomeToGo went public via a SPAC in 2021, reaching a valuation of $1.2 billion after raising $150 million in VC funding. Valentin shares insights into the company’s growth, its approach to balancing marketplace and software solutions, and the strategic importance of acquisitions. The discussion delves into leadership principles, decision-making frameworks, and how HomeToGo navigates market complexities while competing with giants like Airbnb. Valentin also provides an entertaining look at innovative cost-saving measures the company employed, highlighting the unique culture at HomeToGo. This episode is a must-listen for anyone interested in strategic growth, leadership, and the evolving landscape of the vacation rental market.

00:00 Introduction to Between Two COOs

00:16 Valentin Gruber's Background and Home2Go Overview

01:01 Home2Go's Market Position and Public Listing

01:57 Home2Go's Business Model Evolution

05:16 Scale and Transactions at Home2Go

07:19 Subsidiaries and Acquisitions

15:36 Strategic Planning and Problem Solving

22:39 Leadership and Company Culture

24:20 Management Approach and Decision-Making Techniques

25:45 Balancing Learning and Expertise

28:59 The Importance of Pre-Reads in Decision Making

32:41 Leaders Staying Connected to Problems

33:54 Understanding SPACs and HomeToGo's Public Journey

38:20 Strategic Use of SPAC Funds

39:18 Evaluating and Executing M&A Deals

42:05 Memorable Moments and Financial Discipline

46:26 Conclusion and Farewell

Navigating Leadership and Innovation at School of Rock with Stacey Ryan

In this episode of Between Two COOs, host Michael Koenig interviews Stacey Ryan, the COO of School of Rock - a global music school franchise. Stacey debunks a common misconception about the business's origin, noting it predated and inspired the 2003 film. She discusses the operational challenges of managing a global franchise, particularly through the COVID-19 pandemic, and highlights the innovative pivot to remote lessons and live-streamed shows. Stacey also delves into her role in founding Frontwoman.org, aimed at empowering women in leadership roles across various industries. The discussion covers her career trajectory, the importance of mentorship, operational strategies for scaling, and the significant impact of maintaining a supportive and innovative culture for both students and franchisees.

00:00 Welcome to Between Two COOs: Meet Stacey Ryan

00:28 The Real School of Rock: Beyond the Movie

00:52 Empowering Women Leaders: The Mission of Frontwoman.org

02:10 Navigating Challenges: Pandemic Response and Innovation at School of Rock

12:49 Operational Insights: Building a Global Music Education Empire

25:21 Empowering the Next Generation: Talent Assessment and Retention

31:25 Frontwoman.org: Championing Women's Leadership and Empowerment

40:40 Closing Thoughts and Resources