Between Two COO's brings incredible Chief Operating Officers together to share their insights, advice, and crazy stories. Learn from current and former COO's from companies like Tucows, Automattic, Shippo, Chopra Global, & VC firms.
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Automattic's Chief Quality Officer, Lance Willett, discusses the evolution of their open-source culture, maintaining quality at an immense scale, and their innovative AI strategy including support bots and site builders. He shares insights on managing technical operations, driving culture change with standard tooling, and lessons from stabilizing Tumblr. The conversation culminates with profound leadership takeaways, including a quarter-million-dollar mistake that reshaped his perspective.
Get 90 days of Fellow's AI meeting assistant at fellow.app/coo Why Linda still codes on weekends — and what it teaches her about the future of AI (6:00) How AI is changing what Webflow builds — and how fast they build it (3:30–13:00) What happens when websites are no longer built just for humans (14:00) The rise of AEO (Answer Engine Optimization) and what it means for ops (17:00–21:00) Favorite LLMs and workflows — from Claude Sonnet to custom GPTs (23:00–26:00) How Linda builds a culture of in...
Get 90 days of Fellow's AI meeting assistant at fellow.app/coo In this episode, Doug and I cover: Why “AI agent” is more than just a buzzword The difference between deflection and resolution in AI-powered support How Kustomer structures RevOps, GTM, and forecasting What it means to operate with high-context vs. generic playbooks How Doug thinks about team structure, ownership, and cross-functional clarity Predictions for agent-to-agent communication: “Your AI agent will talk to my AI agent—and w...
Get 90 days free with Fellow's AI Meeting Assistant - https://fellow.app/coo Key Takeaways: RevOps aligns and optimizes sales, marketing, and customer success, ensuring efficient and sustainable growth. Effective RevOps requires balancing strategic planning, data-driven analytics, and tactical execution. Successful RevOps integration hinges on clear communication, cultural alignment, and strategic hiring decisions. AI is poised to significantly impact RevOps by improving efficiency, though human...
Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo Timestamps: (02:00) Fellow’s shift from productivity tool to AI assistant. (07:00) Implementing large-scale organizational change. (13:00) Managing change and internal communications. (20:00) Moving toward an agentic, automated workflow future. (23:00) Unexpected real-world AI uses at Fellow. (29:00) Privacy, security, and enterprise-grade compliance. (33:00) Selecting and utilizing LLMs and managing AI economics. (36:00) How to bui...
Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo AI and Privacy: Navigating the EU's New AI Act with Flick Fisher In this episode of Between Two COOs, host Michael Koenig welcomes back Flick Fisher, an expert on EU privacy law. They dive deep into the newly enacted EU Artificial Intelligence Act and its implications for businesses globally. They discuss compliance challenges, prohibited AI practices, and the potential geopolitical impact of AI regulation. For leaders and operators...
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 improv...
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 pos...
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 Vestw...
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 leade...
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 a...
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 act...
Presented by Fellow.app. Streamline your meetings and make them more efficient and meaningful. Get Fellow for you and your team today. Head to https://fellow.app/coo/ to get started and start having better meetings. (00:12) Advice for CEOs and COOs This chapter welcomes Cameron Harold, the founder of COO Alliance and author of "The Second In Command," as we celebrate the release of his new book and examine its content, which serves as a guide for both CEOs and COOs. We explore Cameron's transiti...
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 categori...
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 lear...
(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 Operatio...
(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...
(05:11 - 05:38) Memory and the Evolving Digital Age (06:56 - 08:05) Tech and Memory Retrieval (11:40 - 12:51) Chat GPT and Data Privacy Integration (17:34 - 18:44) Leveraging AI for Company Augmentation (22:34 - 23:47) AI for Efficiency and Exceptional Hiring (30:31 - 31:01) Pivoting to Capture Meeting Data (38:38 - 39:00) COO and Chief of Staff Collaboration (43:27 - 44:27) Using Cultural Values as a Guide (47:10 - 48:20) Accountability and Candor in Successful Teams (55:58 - 57:01) Impressions...
(00:12) Clean Tech and Disrupting Energy Market (06:15) Community Solar and Renewable Energy Innovation (15:37) Data Platform and Energy Transformation (24:21) Acquisitions, Integration, and Board Composition (29:05) Startup Board Management and Risk Balancing (35:51) Leadership, Growth Mindset, and Overcoming Challenges (42:18) Connecting Through Cold Emails (00:12) Clean Tech and Disrupting Energy Market We discuss Energy 101 today with Kate Hemington, co-founder and COO of Arcadia Power. Kate...
--------- EPISODE CHAPTERS WITH SHORT KEY POINTS --------- (0:00:12) - Remote Company Operations and Knowledge Management Daren explains the importance of low context communication, compounding interest, and over communicating for successful remote teams. (0:08:59) - Embracing Remote Work as Operating Model Daren Murph and I discuss operations of successful remote companies, process definition, documentation, culture, macroeconomic downturn, investing in operations, and using history as a guide....
Unlock the secrets of remote team management and product explanation in our stimulating conversation with Nitin Gupta, the COO of Prisma. Nitin unveils how explaining technical products to non-technical people can be a challenge, but he makes it understandable, going as far as breaking down Prisma into simple terms for our mothers. Also, learn about Prisma University, a unique internal initiative to educate non-tech team members about their product's nuances. Beyond product explanation, we ventu...
Join us as we chat with Shanaz Hemmati, the COO of ZenBusiness, who gives us a fascinating insight into the workings of a public benefit corporation that generates more than $100M in ARR. Listen to her as she speaks about the various initiatives and programs that ZenBusiness undertakes to give back to the community and society. From a grant program to support their customers to her role evolution from CIO to COO, Shanaz’s experiences shed light on the strategies they use to navigate their respon...
Join me and our guest, Munish Gandhi, co-founder and COO of Productiv, as we unravel the intricacies of SaaS governance and optimization. We talk about how the rapid growth of SaaS applications, fueled by a wealth of funding, has led to a lax approach to purchasing and implementing applications. Munish expertly guides us through the function of Productiv, explaining how it provides valuable insights and recommendations for SaaS portfolio governance, rationalizing SaaS spending, and refining SaaS...
Join us as we sit down with Allen Narcisse, former COO at Workrise and co-founder and CEO of Gigs, for an enlightening conversation about his journey in the gig economy. Allen takes us through his career trajectory, starting from his initial venture, eBuyLine, to his stints building Uber and Lyft, and finally, to his current venture, Gigs. Listen in as Allen shares valuable insights on building marketplaces, the importance of a great first impression, and the inspiration behind Gigs. In the seco...
Can we really grow sustainable, delicious, and healthy food right in the heart of a bustling city? In this eye-opening episode, I had the pleasure of chatting with Tobias Peggs, co-founder and CEO of Square Roots, an innovative indoor urban farm tech company that's revolutionizing how we grow and distribute food in urban areas. Together, we explored the intricate operations of creating a successful indoor urban farm, from engineering and construction to farming and distribution processes. Tobias...
Stephan Jacob, Co-founder and COO of Cotopaxi, joins Michael to talk about building an impact-driven business, how sustainability drives Cotopaxi’s product development, managing a CEO transition, the proliferation of certified B Corps, donating revenue to fight poverty in developing countries, brand building and taking on North Face and Patagonia, and taking llamas on college campuses. With a humanitarian-drive and strong business acumen, Stephan’s career in the COO seat began at Cotopaxi, follo...
Woody Hartman, COO of Lime and former VP of Global Operations at Lyft, sits down with Michael to talk about the challenges in scaling a micro-mobility company, how Lime’s gained a competitive advantage over other players in the market, and why he chose to climb Mount Everest following his time at Lyft! A biz ops wizard, Woody’s career started as a Business Analyst at McKinsey in 2006, focused on M&A and private equity due diligence. With a passion for creating joyful customer experiences, Wo...
On this week’s episode, Michael’s joined by Felicity “Flick” Fisher, Partner and de facto COO of the law firm, Fieldfisher. Flick breaks down all things privacy and data related, including the European Union’s General Data Protection Regulation, where privacy and data laws may be headed, and the impact privacy advocates have had on the space. Now amongst the top InfoSec legal experts, Flick’s journey in the space began when she moved to the Bay Area in 2015. Initially joining her firm, Osborne C...
Holger Seim, co-founder, and CEO of Blinkist, speaks with Michael about how Blinkist emerged out of shifting consumption patterns, where the company may be headed in the future, and how to stay true to your long-term strategic vision while also incorporating the thoughts and ideas of other stakeholders. With an entrepreneurial spirit that emerged during his childhood in Germany, Holger’s journey has been guided by his unsatiated love of building things from the ground up. Leaning further into th...
Diego Camberos, COO of Vodafone Qatar and former CEO of Tigo Millicom Senegal and Rwanda, joins Michael to share insight into navigating cultural differences in different markets, how “radical simplification” has served as the bedrock of Vodafone’s success, and how to build a corporate culture that acknowledges and respects different cultures. A citizen of the globe, having spent time living in several countries outside his home country of Bolivia, Diego has expertise across various departments,...
