From Zocdoc to Cascade, COO Anna Elwood breaks down the systems, rhythms, and AI tools that turn chaos into execution. In this episode of Between Two COOs, Michael sits down with Anna Elwood, COO of Cascade, the strategy-execution platform helping companies turn plans into results. Anna shares how she evolved from Broadway actor to operator, scaling companies like Zocdoc, Knotel, and Teachable before joining Cascade to build the muscle of strategy execution. She explains how to create an “operating rhythm” that keeps teams aligned across time zones, the tension between governance and red tape, and how Cascade helps leaders link vision to measurable execution. The conversation dives deep into AI’s role in operations, the future of hybrid work, and what it takes to move from chaos to clarity in a global startup. Anna’s storytelling — especially her account of leading through Superstorm Sandy — highlights what real-time operational leadership looks like when everything goes sideways.

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo In this episode, Michael Koenig sits down with longtime friend and colleague Lance Willett, Chief Quality Officer at Automattic—the company behind WordPress and WooCommerce. The two dive deep into the evolution of open source at scale, the overlooked role of technical operations, and how quality shapes everything from uptime to user trust. They also unpack how Automattic is integrating AI across products, lessons from acquiring Tumblr, and the leadership values Lance learned directly from Matt Mullenweg.

Get 90 days of Fellow's AI meeting assistant at fellow.app/coo In this episode of Between Two COOs, I’m joined by Linda Tong, the CEO of Webflow. You probably know Webflow as one of the most popular visual development platforms on the internet, powering over 300,000 websites. What you may not know is that Webflow is going all-in on AI – not just in product, but across operations, marketing, and internal tooling. Linda and I get into the hard questions: • What happens to websites when bots, not humans, are the primary visitor? • What’s the real impact of agentic AI on company structure? • How do you lead a team when timelines are collapsing and the tech changes weekly? We also talk about why AI hasn’t just boosted productivity at Webflow — it’s let them build entirely new capabilities that weren’t possible before. Plus: how she thinks about scaling innovation inside a growing org, how her product background shapes how she leads, and a behind-the-scenes story of navigating the SVB bank run from the COO seat. This one goes deep — from tooling to team culture to what’s next for the internet.

Get 90 days of Fellow's AI meeting assistant at fellow.app/coo Doug Hanna, President & COO of Kustomer (acquired by Meta), returns to the pod for Episode 51 of Between Two COOs. This time, we’re talking about AI—specifically agentic AI—and how it’s reshaping customer service, GTM workflows, and operational leadership. Doug shares real examples of how Kustomer’s AI agents are resolving tickets, not deflecting them—and why the real power lies in agent-to-agent collaboration. We also cover RevOps structure, sales forecasting frameworks, the problem with over-relying on generic playbooks, and how to operate with high context at scale.

In this episode of Between Two COOs, Brad Rosen, President at Sales Assembly, takes us deep into the world of Revenue Operations (RevOps)—a critical function focused on aligning and optimizing sales, marketing, and customer success operations. Brad shares insights on why RevOps has become indispensable in driving sustainable and efficient growth, highlighting practical ways organizations can effectively leverage this function. He explores the challenges of defining and scaling RevOps, breaking down silos within teams, and managing the balance between strategic decision-making and tactical execution. Brad also shares his perspective on how AI is impacting RevOps, the role of human judgment, and best practices for leaders aiming to adopt or enhance their operational capabilities.

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo In this episode, Aydin Mirzaee, CEO and founder of Fellow, returns to discuss Fellow’s dramatic evolution from a meeting productivity tool into a full-fledged AI-powered operations assistant. Aydin shares insights into how Fellow pivoted successfully to an AI-first strategy, highlighting both the internal transformation and external market demands driving the shift. Key themes include implementing AI at scale, navigating significant organizational change, ensuring strong internal communication, and addressing security and compliance challenges inherent to AI. The conversation also explores how operational leaders can effectively integrate AI into workflows, and predictions on the future of AI-driven operations.

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo In this insightful episode, Flick Fisher delves deep into the newly enacted European Union Artificial Intelligence Act (EU AI Act), exploring its comprehensive framework aimed at regulating AI with a human-centric, risk-based approach. Fisher details the categories of AI defined by the Act—Prohibited, High-Risk, and General AI—and highlights the stringent compliance and transparency requirements now faced by global businesses. The conversation emphasizes the significant implications for companies operating internationally, enforcement mechanisms, potential penalties, and the broader geopolitical considerations between the EU, US, and China.

In this episode of Between Two COOs, Michael Koenig sits down with Justin Etkin, COO of Tropic.io, to discuss how procurement has evolved into a strategic function in today’s businesses. Justin shares his insights on how companies can use procurement as a growth lever rather than just a cost-saving measure, the impact of AI on procurement, and best practices for negotiation. If you’re a COO, CFO, CEO or anyone dealing with vendor contracts, this episode is packed with actionable insights on optimizing procurement. Don't forget to check out www.fellow.app/coo for a 90-day free trial of their AI Meeting Assistant.

In this episode of Between Two COOs, Michael Koenig interviews Evan Grossman, partner and head of the CEO and board practice at True Search, one of the world’s leading executive recruiting firms. Evan shares insights into the hidden C-suite job market, the importance of networking, and how to position yourself for a top executive role. The conversation delves into the nuances of executive hiring, including mitigating risk with non-traditional candidates, leveraging AI for scale in recruiting, and how companies identify and evaluate board members. Evan also discusses career growth strategies for COOs aspiring to become CEOs, emphasizing the value of cross-functional experience and self-awareness. Anecdotes about the tight-knit nature of the executive ecosystem underscore the importance of humility and relationships in the hiring process.

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.

In this episode of 'Between Two COOs,' host Michael Koenig interviews Valentin Gruber, COO of Home2Go. The conversation covers Home2Go's history, its public listing via SPAC in 2021 with a valuation of $1.2 billion, and the company's strategic direction. Valentin discusses their approach to navigating the crowded vacation rental market, emphasizing their transition from a meta-search platform to a marketplace providing tech solutions for smaller partners. The discussion also delves into Home2Go's strategic acquisitions to augment their offerings and Valentin’s views on maintaining a culture of self-critique and detailed understanding among leaders. The conversation is enriched with anecdotes about their cost-effective IPO celebrations and unique M&A experiences.

Empowering Leadership and Innovation with Stacey Ryan of School of Rock In this episode of Between Two COOs, host Michael Koenig interviews Stacey Ryan, the COO of School of Rock, a global music school franchise. Despite common beliefs, the School of Rock predated its namesake 2003 film, with Stacey clarifying that the film was, in fact, inspired by the school’s real-life operations. Stacey discusses the significant impact of the global pandemic on the business, highlighting the shift to remote music lessons as a major innovation that the School has retained post-pandemic. She emphasizes the importance of community and mental health support for students, demonstrating how challenges like COVID-19 spurred innovation and team cohesion within School of Rock. Additionally, Stacey delves into operational challenges, the franchise model, and strategic international expansion. She also speaks on her personal journey, shedding light on creating frontwoman.org, a nonprofit focused on empowering women leaders across industries. Throughout the episode, Stacey shares insights on leadership, the value of community, and the transformative power of music education. 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: The Pandemic's Impact on School of Rock 05:27 Innovating Through Crisis: Adapting to a Pandemic World 08:58 Building a Community: The Power of Music and Belonging 12:49 Operational Excellence: Stacey's Approach to Efficiency 22:28 Expanding Horizons: International Growth and Master Franchising 31:25 Empowering Future Leaders: The Vision Behind frontwoman.org 40:40 Closing Thoughts and Future Directions

In an insightful episode of 'Between Two COOs,' host Michael Koenig converses with Aidan Mirzaee, the founder and CEO of Fellow, about the art and science of optimizing meetings. The discussion dives into the staggering statistics of daily meetings in the U.S., the inception of Fellow as a product to optimize structured management processes, and Shopify's drastic measure to save hundreds of thousands of hours by canceling recurring meetings. Reflecting on personal experiences, Aidan shares his journey from managing a scrappy startup to embracing structured management processes post-acquisition by SurveyMonkey, leading to the realization that optimizing meetings is crucial for managerial efficiency. The conversation also touches on implementing Fellow at scale within companies like Shopify, the importance of action items in meetings, and the balance between meeting frequency and productivity. Additionally, they explore the role of AI in enhancing meeting efficiency and safeguarding proprietary information while fostering innovation. Aidan shares insights from leading Fellow, emphasizing the need for adaptable management styles, fostering company culture, and the transformative potential of AI in business processes. A lively discussion ensues about the uniqueness of remote meetings and the value of asynchronous communication. This episode not only provides a deep dive into the world of meetings and management but also offers actionable insights for leaders aiming to optimize their team's time and effectiveness.

Join me, Michael Koenig, on a journey with business guru Cameron Harold, as we celebrate his latest literary achievement, "The Second In Command." Listen in as Cameron, the brain behind COO Alliance, unpacks the essentials of his new book, offering a treasure trove of guidance for CEOs and COOs alike. Discover the pivotal shifts Cameron experienced transitioning from COO to CEO and how this evolution informed his approach to balancing work and life. His candid sharing of early business challenges and the power of delegation, saying no, and zeroing in on crucial tasks provide actionable advice for any business leader. In our discussion, we tackle the nuanced decision-making process between promoting from within versus bringing in external talent. I share personal anecdotes, drawing parallels between the relentless improvement seen in elite sports and fostering a growth-oriented culture within organizations. We delve into the sentimentality of sports heroes, my encounter with Ken Dryden, and how these experiences shape our understanding of leadership. Furthermore, Cameron and I dissect the organizational agility, emphasizing a "bobbin' weave culture," and how a flexible mindset can steer a company towards its vivid vision. Wrapping up this enlightening episode, we explore the impact of AI tools in business efficiency, with a nod to COO Alliance members' innovative weekly AI experimentation. The conversation pays homage to lauded COOs like Cheryl Sandberg and Matt Rawlings, whose leadership exemplifies the blend of effective management and creativity. And finally, I extend heartfelt thanks to Cameron for his invaluable insights, underscoring the significance of his book for strengthening leadership teams and the overall health of organizations. Tune in for this engaging exploration of leadership, technology, and the potent dynamic between CEOs and COOs. Proudly sponsored by Fellow. Get better meetings today at https://fellow.app/coo/.

How you need to plan for the AI Act? What is permissible and isn’t? How the EU will regulate AI? What constitutes AI? 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.

Join us as Greg Strickland, COO of Productboard, and I explore the power of embracing new opportunities and the crucial balance between business outcomes and personal advancement. Greg shares his journey of growth through accepting challenges that push boundaries, and we reflect on the times when a strategic 'no' can pave the way for others' development and align with company goals. Listen in for an insightful discussion on the mentorship gap in early-stage companies and the trial-and-error learning that COOs like Greg navigate in the startup landscape. As the startup ecosystem continues to evolve, we dissect the influence of continuous learning on company culture, inspired by industry pioneers. I open up about the enriching experience of partnering with product and engineering-driven founders and how passion plays a decisive role in a startup's trajectory. We consider how startups like Productboard are innovating in operations and product management with the use of AI, highlighting the agility required to manage rapid change and the ethical considerations of handling customer data. In our conversation, we delve into the challenges of scaling up to the enterprise market and the importance of building a culture that can gracefully manage internal friction points. I share my approach to fostering empathy and collaboration across departments, revealing personal anecdotes and strategies for aligning diverse perspectives within a company. Tune in for a rich discussion full of practical insights, memorable moments, and tips for nurturing a successful startup environment. Follow Productboard on LinkedIn and check out their blog for more engaging content that can help steer your company towards growth and innovation.

Unpack the transformation of travel experiences with me, Michael Kanig, as Tao Tao, COO of GetYourGuide, reveals the secrets behind turning a dorm-room startup into a $2 billion industry titan. We're setting the stage for a fascinating tale of innovation, strategy, and resilience that's reshaping the way people discover and book their adventures. From the early days as a fledgling peer-to-peer network to its current stature as a global connector of travelers and professional activity providers, GetYourGuide's story is a masterclass in adaptability and foresight, particularly in embracing the digital revolution that's now a $300 billion opportunity. As we navigate the company's journey, Tao and I explore the crucial role of company culture in weathering the storms of the industry, including the unprecedented challenges of the COVID-19 pandemic. We share the strategic thinking behind maintaining a cohesive team, underpinned by core values that not only helped survive tough times but also primed the company for a vigorous comeback. The episode also delves into the pandemic's silver lining – a rapid transition to digital engagements that's redefining the travel experience for millions around the globe. Rounding out our conversation, we look at the art of crafting a board of directors that aligns with a company's vision and the nuances of navigating Series F funding amidst a complex tech investment landscape. Tao provides a window into GetYourGuide's future, driven by a technology-first approach aimed at enhancing customer experiences and expanding inventory. Plus, we contemplate the exciting potential of AGI and chat GPT technologies to revolutionize the travel industry further. If your wanderlust is calling, let this episode be the first step in your next journey, and don't hesitate to reach out to Tao on LinkedIn to continue the conversation.

Are you ready for a deep dive into the world of remote work, productivity, and leadership? Let us whisk you away on a journey with our special guest, Alan Christensen, the COO of Duist, a trailblazing SaaS company. Alan’s story, which starts from humble beginnings in a family pipe business, catapults into an unlikely tech career, is an inspiration to us all. He sheds light on the dynamic relationship between a CEO and COO, and how their duties are divided at Duist. Get ready to be inspired, as we uncover the secrets of Duist's success without traditional institutional investments. Now let's shift gears and look to the future - a future where remote work is at the forefront. As we navigate this new landscape, we find ourselves pondering the role of asynchronous communication in remote work settings. What makes it so effective? How does it influence work-life balance? And even more tantalizing, how exactly does it promote a more productive work environment? Join us as we discuss these burning questions and share our experiences utilizing our product, Twist, to foster asynchronous communication within our own team. We delve into the crucial role of documentation and transparency in remote work, ensuring that decisions are not just made but also recorded for future reference. Lastly, we tackle the important topics of recruitment, career growth, and feedback processes. Hear about our unique hiring system and how it's shaped our company culture. Our discussion evolves towards career progression and the importance of having a proper framework for career growth. Learn how we have recently adopted a new platform for professional development, and how we manage the challenges of leading a remote team. And for a twist, you won't want to miss Alan's account of an odd trademark infringement case, displaying the lengths some will go, even without a case. So buckle up, and join us for this enlightening conversation about the evolving world of work.

We're thrilled to welcome Dan Sroker, co-founder and CEO of Rewind, and former CEO and co-founder of Optimizely, to Between Two COOs! This episode centers around an eye-opening conversation about the potential of AI to augment human memory, transforming every digital interaction into an AI-able, searchable database. Yes, you heard it right! We are talking about having a "superpower" that could change the way we perceive and utilize our memory. During the discussion, we also shine a light on the future of AI in operations, how it can amplify human capabilities, and importantly, the full impact on productivity. However, we don't shy away from the hard questions either. There is a crucial conversation on privacy and security in AI, and the stark warning that those businesses not getting on board may well struggle in the future. We also navigate through the role of AI in remote work and the possibility of smaller teams punching above their weight with the help of technology. Lastly, we touch upon the prime importance of STEM education in fostering creativity and problem-solving skills, and how it finds its place in the world of technology. We discuss the dynamics of having a COO and chief of staff, why company values matter, the importance of psychological safety in team building, and the art of conducting effective reference checks during hiring. This episode is a riveting exploration of how technology intertwines with our lives and how we can make it work for us. Tune in for an enlightening discussion!

The compelling Kate Hemington, co-founder and COO of Arcadia Power, joins us for a deep dive into the revolutionary world of clean tech and the disruption of the energy market. Her unique insights, stemming from her academic background at the University of Oxford and experience in corporate litigation, shed light on how Arcadia Power leverages digitization in the traditionally regulated energy industry. Through our enlightening conversation, we navigate the dynamics of energy monopoly and how the legal and policy perspective can create unique opportunities. We venture into the intricate world of community solar and renewable energy, unraveling how states incentivize third-party developers to build renewable power sources. Kate reveals how Arcadia Power simplifies this process for customers by providing a guaranteed savings rate. The conversation illuminates how community solar is not only beneficial for customers but is also instrumental in replacing dirty electrons with clean ones. Our discussion also explores how Arcadia Power's data platform, Arc, is used to retrofit billions of machines for maximum decarbonization. Get ready to uncover how this data empowers other companies to help their customers make micro-decisions. We also discuss the complexities of managing acquisitions, integrating products, and board composition in a startup environment. The dialogue emphasizes the importance of strong leadership, a growth mindset, and effective communication in overcoming challenges. The episode wraps up with an intriguing discussion on the power of cold emails to forge impactful connections. Tune in to this riveting episode to gain a deeper understanding of the clean tech revolution.