Don't forget to check out www.fellow.app/coo for a 90-day free trial of their AI Meeting Assistant.

[00:00] Introduction – Michael introduces Fellow as a trusted AI meeting assistant.
[01:00] Welcome to Between Two COOs – Introducing Justin Etkin and Tropic.io.
[02:00] The evolution of procurement – From cost-cutting to strategic value creation.
[05:00] When should companies start formalizing procurement?
[07:00] Common mistakes businesses make in procurement.
[10:00] Using data and AI to improve procurement efficiency.
[12:00] Negotiation strategies and dealing with vendors.
[16:00] The role of AI in procurement and automation potential.
[20:00] How companies are shifting towards integrated procurement platforms.
[23:00] The intersection of procurement and legal, finance, and security.
[28:00] Justin’s wildest COO experience – Painting walls before an office move-out.
[30:00] Closing thoughts – Where to follow Justin and learn more about Tropic.io.

Tropic - https://www.tropicapp.io/

Between Two COO's - https://betweentwocoos.com

Episode URL - https://betweentwocoos.com/tropic-coo-justin-etkin

Michael Koenig - https://linkedin.com/in/michael-koenig514

Justin Etkin - https://www.linkedin.com/in/justintropic/

Don't forget to check out www.fellow.app/coo for a 90-day free trial of their AI Meeting Assistant.

This episode is powered by Fellow AI Meeting Assistant. Get 90 days free at fellow.app/coo

Key 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 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

Maximizing Meeting Efficiency and Navigating Management Challenges: Insights from Aidan Mizrahi of Fellow

This episode delves into the complexities and potential inefficiencies of meetings in the professional world, emphasizing the staggering number of unproductive meetings held daily. Highlighting the innovative approach of Shopify in canceling recurring meetings to save significant time, the conversation introduces Fellow, a SaaS product aimed at optimizing meeting structures, agendas, and action items to enhance management processes. Aidan Mizrahi, the CEO of Fellow, shares his journey from being unaware of structured management processes to creating a platform that serves as a manager's co-pilot, focusing on the intricacies of managing differently for every team member and adapting over time. Furthermore, Mizrahi discusses the pivotal role of asynchronous meetings in remote work, the significance of setting meeting norms, and leveraging AI to improve efficiency and decision-making in organizations. The episode also explores the balance between security and innovation when integrating AI into business processes and concludes with Mizrahi sharing a personal anecdote on how AI has become a part of his daily routine for brainstorming and learning.

00:00 The Meeting Epidemic: Unveiling the Problem

00:58 Introducing Fellow: The SaaS Revolutionizing Meetings

01:42 A Deep Dive into Fellow's Origin and Mission

01:50 From Startup to Acquisition: A Journey of Learning and Growth

05:14 The Power of Structured Management Processes

09:43 Implementing Effective Meetings at Scale with Fellow

15:51 Optimizing Meetings for Action and Accountability

20:00 Redefining Meeting Culture: Strategies for Efficiency

29:06 Embracing Remote Work: The Future of Meetings

32:37 Unlocking the Power of Asynchronous Meetings

33:43 The Value of Time and Asynchronous Work

35:18 Inside the Operations of Fellow: Mastering Efficiency

35:44 The Art of Meeting Types and Decision Making

40:21 Leveraging AI for Business Efficiency and Innovation

45:58 Navigating AI Ethics and Security in Business

48:34 AI Presentations: Sharing Knowledge and Inspiring Innovation

56:03 The Impact of Super Managers Podcast on Leadership

01:02:07 Exploring New Frontiers with AI: A Personal Experiment

01:04:41 Connecting with the Community and Wrapping Up

Could the EU's new AI Act be the cornerstone of global AI regulation? That's what we're here to unpack with the expert insight of Flick Fisher, a leading privacy specialist and partner at Fieldfisher. As the digital age accelerates, the European Union is setting a precedent with the AI Act, a groundbreaking legislation designed to navigate the complex terrain of artificial intelligence. Flick and I dissect the Act's risk-based approach, dissecting the prohibited and high-risk AI systems categories, while giving a nod to the lighter touch on low-risk innovations. Our conversation delves into how this monumental regulation could shape data privacy and ethical AI practices on the world stage.

Join us as we explore not only the definitions and distinctions within the AI Act but also its everyday implications for business operations, from HR decisions to the product safety landscape. With generative AI technologies like ChatGPT on the rise, understanding the nuances of this legislative framework has never been more crucial. We'll navigate the potential new compliance roles the Act may create and predict whether this regulatory move could become the global gold standard. Tune in for a comprehensive analysis that will equip COOs and business leaders with the foresight needed to thrive in an AI-governed future.

(00:06) EU AI Act and Its Impact

(11:50) Regulations and Definitions of AI

(27:38) The Implications of the AI Act

Links

Episode link: https://www.betweentwocoos.com/the-eu-vs-ai-the-legal-opinion-with-flick-fisher-partner-at-fieldfisher/

Flick's previous episode on GDPR: https://www.betweentwocoos.com/data-privacy-gdpr-flick-fisher/

Flick on LinkedIn: https://www.linkedin.com/in/felicityfisher/

Fieldfisher: https://www.fieldfisher.com/

Between Two COO's: https://www.betweentwocoos.com/

Michael Koenig on LinkedIn: https://linkedin.com/in/michael-koenig514/