This episode is powered by Fellow AI Meeting Assistant. Get 90 days free at fellow.app/cooKey Takeaways:• Hidden C-Suite Job Market: The majority of C-level roles are filled through networking, talent partners, and executive recruiters before job postings are even considered.• Role of Networking: Building strong relationships within your industry and maintaining top-of-mind positioning with decision-makers is crucial.• Non-Traditional Candidates: Market shifts, such as the rise of AI and post-COVID changes, are creating opportunities for candidates from unconventional backgrounds.• AI in Executive Recruiting: True Search uses AI-driven tools like Thrive to manage data at scale, identifying the best candidates more efficiently.• Career Advice for COOs: Gaining hands-on experience in both value creation (product/tech) and value capture (go-to-market) functions can prepare COOs for CEO roles.• Culture Fit: Evaluating culture fit involves assessing how a candidate aligns with and enhances the company’s existing culture without disrupting it.• The Board Member Journey: To be considered for a board position, candidates need specialized expertise and experience managing boards or navigating complex organizational challenges. Notable Quotes:• “Position yourself within your network as someone ready to step into a C-level role—start those conversations early.”• “If everyone’s a thought leader, no one is a thought leader. Focus your voice and expertise on what truly adds value.”• “To be a successful CEO, you need to have hands-on experience in both product and go-to-market functions.” Evan’s Unforgettable Moments:• Two finalists in a CEO search accidentally meeting mid-interview process due to scheduling overlap—illustrating the small-world nature of the C-suite ecosystem.• Delivering news to two candidates while they stood together on the sidelines of their kids’ soccer game, showing how interconnected the executive world can be. Be sure to check out Fellow's AI Meeting Assistant and get 90 days free at fellow.app/coo.

Episode OverviewIn 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 Covered1. 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 HostMichael 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 COOs00:16 Valentin Gruber's Background and Home2Go Overview01:01 Home2Go's Market Position and Public Listing01:57 Home2Go's Business Model Evolution05:16 Scale and Transactions at Home2Go07:19 Subsidiaries and Acquisitions15:36 Strategic Planning and Problem Solving22:39 Leadership and Company Culture24:20 Management Approach and Decision-Making Techniques25:45 Balancing Learning and Expertise28:59 The Importance of Pre-Reads in Decision Making32:41 Leaders Staying Connected to Problems33:54 Understanding SPACs and HomeToGo's Public Journey38:20 Strategic Use of SPAC Funds39:18 Evaluating and Executing M&A Deals42:05 Memorable Moments and Financial Discipline46:26 Conclusion and Farewell 

Navigating Leadership and Innovation at School of Rock with Stacey RyanIn 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 Ryan00:28 The Real School of Rock: Beyond the Movie00:52 Empowering Women Leaders: The Mission of Frontwoman.org02:10 Navigating Challenges: Pandemic Response and Innovation at School of Rock12:49 Operational Insights: Building a Global Music Education Empire25:21 Empowering the Next Generation: Talent Assessment and Retention31:25 Frontwoman.org: Championing Women's Leadership and Empowerment40:40 Closing Thoughts and Resources

Fellow CEO, Aydin Mirzaee, discusses optimizing meeting efficiency with AI, emphasizing the epidemic of unproductive meetings, the inception of Fellow as a SaaS product to revolutionize meetings, the importance of structured management processes, the role of AI in decision-making, setting meeting norms, and balancing security with innovation. Also, shares personal AI integration anecdotes for brainstorming and learning.

Cameron Herold, founder of COO Alliance and author of 'The Second In Command,' discusses his transition from COO to CEO, the mindset shifts that accompanied this change, and the importance of delegating and focusing on critical tasks. The podcast also explores promoting from within versus hiring externally for COO role and strategies for fostering a safe environment where feedback is welcomed. Additionally, the episode touches on using Fellow to solve the meeting problem, embracing AI as a tool, and the importance of adapting and thriving as a leader.

Flick Fisher, leading privacy specialist and partner at Fieldfisher, discusses the EU's AI Act and its risk-based approach to regulating AI systems. They explore high-risk systems, prohibited AI, and the implications for business operations. They also discuss concerns about stifling innovation and speculate on the global impact of this regulation.

COO of Productboard, Greg Strickland, discusses embracing new opportunities, mentorship in early-stage companies, continuous learning, innovation with AI, scaling up to enterprise market, fostering empathy and collaboration, and personal anecdotes of executives fighting over candidates.

(01:20 - 02:44) The Travel Experience Market's Growth(04:36 - 06:03) Peer to Peer Tour Guide Platform(07:27 - 09:26) Learning and Customer Obsession Importance(12:35 - 13:56) Creativity and Execution in Strategy(16:11 - 17:06) Identifying Core Values for Company Culture(21:48 - 23:03) Accelerating Digitization and the QR Code(36:32 - 37:43) Investment Strategy and Flywheel Approach(39:48 - 40:47) International Tensions and Investment Impacts(43:17 - 44:43) Applying AGI and AI to Operations  (00:11) The Travel Experience Industry Journey This chapter welcomes Tao, COO of GetYourGuide, to share insights into the burgeoning travel experience industry. I explore how GetYourGuide, a company that started in a dorm room, grew into a $2 billion enterprise, selling over 80 million tickets to travelers seeking unique experiences, such as private tours of the Vatican Museum. We look at the travel experience market as an untapped online frontier, previously dominated by offline transactions and now worth $300 billion. Tao recounts the founding story of GetYourGuide, from its original concept as a peer-to-peer platform for tour guides to pivoting towards professional activity operators, marking the beginning of its success. We also touch upon the company's recent $194 million funding round and discuss the increasing trend of travelers preferring experiences over material possessions. (13:56) Adapting Culture and Surviving Crisis This chapter begins by exploring the integration of culture with changing strategies, emphasizing the importance of a consistent culture that supports shifts without causing disruption. I discuss the development of authentic core values by sharing a story of initial failure and eventual success through a reflective process with the leadership team, highlighting the key role of core values in determining who fits within a company. The conversation then pivots to the impact of COVID-19, recounting the immediate challenges and strategic decisions made in response to the pandemic, including the choice not to lay off staff and to continue investing in the future. The chapter concludes with an optimistic outlook, noting a strong recovery and promising prospects for the years following the initial crisis. (21:10) Travel Industry This chapter focuses on how businesses adapted during the pandemic, particularly addressing the balance between long-term planning and immediate operational needs. We touch on innovative measures like salary sacrifices for stock options and government-subsidized work hour reductions. We highlight the insights gained from having co-founders with molecular biology backgrounds, which helped us stay ahead in understanding the virus's impact on the travel industry. Additionally, we discuss the acceleration of digitization due to the pandemic, using the QR code's newfound ubiquity as a prime example. This digital shift significantly impacted operations, especially for our partnerships with historical attractions and museums, which had to quickly adapt to digital ticketing and queue management. Lastly, we examine the surge in travel as restrictions lifted, debunking the idea that the spike was merely 'revenge tourism' and noting the persistent trend towards domestic tourism. (31:53) Board Members, Funding, Global Network Effects This chapter focuses on the strategy behind assembling a board of directors for a private company, highlighting the importance of selecting members who bring expertise and accountability. We explore the company's recent Series F funding round, which includes a mix of cash and a revolving credit facility, designed to provide financial flexibility. The significance of raising funds during a period when many tech companies struggle is discussed, emphasizing the company's steady growth and prudent financial practices that have led to a successful up-round without resorting to complex financial instruments. I share insights into the deployment of the raised capital, underlining the company's investment into a technology-driven flywheel model, which encompasses building customer audience, enhancing the product, and acquiring a diverse inventory to support their mission of expansion, particularly in the U.S. market. (40:48) Travel and AGI Building Connections This chapter begins with reflections on the value of a connected world and the peace dividend concept, emphasizing how less military spending can boost investment in other sectors like technology and education. I examine the impact of decoupling on trade efficiency and express hope for the role of travel in fostering empathy and cultural understanding. I share insights on the potential of AGI and chat GPT to transform operations in various fields, including machine learning, translation, customer service, and personalized recommendations. I highlight the impressive capabilities of AI in instant translation, which can facilitate global communication and commerce. Lastly, I recount the startling experience of near-zero revenue during COVID-19 and discuss how resilience led to recovery. To keep up with these themes, I encourage listeners to use GetYourGuide for their travels and connect with me, Tao Tao, on LinkedIn. Links: Playing to Win: How Strategy Really WorksThe Mind of the StrategistAmazon's Leadership PrinciplesNetflix's Core ValuesDelivering Happiness Turning on the Lights at the VaticanGetYourGuideEpisode URLMichael Koenig on LinkedIn

(00:12) Interview With Remote COO Alan Christensen COO Alan Christensen shares his journey and Duist's success without institutional investment, pioneering remote work and dividing responsibilities with CEO. (11:48) Future of Remote Work and Communication Remote work's significance in shaping the future, utilizing asynchronous communication, transparency, and documentation for effective management. (22:28) Recruitment, Career Growth, and Feedback Processes Hiring, company culture, flat hierarchy, career development, and professional growth are emphasized by the speaker. (31:04) Challenges With Trademarks and Feedback Remote company Todoist's values, challenges, hands-on management, stable squads, feedback framework, and trademark infringement case.