Shows
Between Two COO's with Michael KoenigKustomer COO & President, Doug Hanna, on Building Agentic AI, Running Sales, and Structuring Modern Ops Teams for the AI EraGet 90 days of Fellow's AI meeting assistant at fellow.app/cooIn this episode, Doug and I cover:Why “AI agent” is more than just a buzzwordThe difference between deflection and resolution in AI-powered supportHow Kustomer structures RevOps, GTM, and forecastingWhat it means to operate with high-context vs. generic playbooksHow Doug thinks about team structure, ownership, and cross-functional clarityPredictions for agent-to-agent communication: “Your AI agent will talk to my AI agent—and we’ll both just read the summary.”Timestamps:(02:00) Defining agentic AI in customer service(06:30) From deflection to resolution: Kustomer’s AI in action...2025-06-0446 min
Between Two COO's with Michael KoenigSales Assembly President, Brad Rosen, on Unlocking Growth and Why RevOps Is Critical for Sustainable ScalingGet 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 judgment remains crucial.Metrics and KPIs in RevOps must directly correlate to revenue growth, profitability, and organizational efficiency.B...2025-04-2946 min
Between Two COO's with Michael KoenigThe Bold Pivot: From Meetings to AI with Aydin Mirzaee, CEO of FellowTry Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/cooTimestamps:(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 build an AI-first company from scratch.(40:00) Why existing companies struggle to adopt AI effectively.(44:00) Practical advice on starting AI...2025-04-1547 min
Between Two COO's with Michael KoenigAI and Privacy: Navigating the EU's New AI Act & the Impact on US Companies with Flick FisherTry Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/cooAI and Privacy: Navigating the EU's New AI Act with Flick FisherIn 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 navigating AI in business, this episode provides crucial insights into managing AI technology within regulatory...2025-04-0136 min
Between Two COO's with Michael KoenigCut Your SaaS Costs: COO Justin Etkin on Smarter ProcurementDon'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 toward...2025-02-0543 min
Between Two COO's with Michael KoenigVestwell COO Jon Mark on applying strategy and tactics to build a multi-billion dollar companyEpisode 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 i...2025-01-0851 min
Between Two COO's with Michael KoenigEU vs AI: What You Need to Know About the EU's AI Act - The Legal Opinion with Flick Fisher, Partner at FieldfisherCould 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...2024-01-3033 min
Between Two COO's with Michael KoenigProductboard COO Greg Strickland on how to balance growth and innovation, collecting mentors and personal development, managing through change, SMB to enterprise shift, and the competitive advantage of startupsJoin 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 d...2024-01-2452 min
Between Two COO's with Michael KoenigPrisma COO, Nitin Gupta, explains tech to my mom, operationalizing hackathons, the balance of commercializing open-source, planning, and a team psychologistUnlock 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 venture into the world of remote hackathons and the operational challenges within. Nitin highlights anticipating potential issues within a remote team a...2023-09-2645 min
Between Two COO's with Michael KoenigProductiv COO, Munish Gandhi on Harnessing AI for Streamlining Contract Renewals and Procurement, Optimizing SaaS Costs, Governance and Risk Management, SVB's Collapse, and moreJoin 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 procurement. We also delve into the issue of SaaS underutilization, considering how incentives from SaaS companies, the excitement of software purchases, and the...2023-08-0140 min
Between Two COO's with Michael KoenigFormer Workrise COO and current CEO of Gigs, Allen Narcisse on transforming the labor market, building Uber Eats, Lyft, and Gigs, and the impact of AI and automation on jobs 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 second part of our discussion, we explore the intricacies of operating a gi...2023-07-1844 min
Between Two COO's with Michael KoenigEmbracing the Future of Food: The Rise of Sustainable Indoor Urban Farming with Square Roots CEO Tobias PeggsCan 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 shared fascinating insights on how Square Roots uses cutting-edge technology to minimize its environmental impact, reduce its carbon footprint, and...2023-06-2738 min
Between Two COO's with Michael KoenigGoodworld CEO, Dale Pfeifer on scaling social impact via tech, Mastercard, Citi, & BlackRock's leadership in corporate social responsibility, pandemic's impact on accelerating CSR, pitching President Obama, & moreDale Pfeifer, CEO of Goodworld, chats on scaling social impact through tech, the evolution of CSR (corporate social responsibility) from consumer targeted to greater corporate involvement, Mastercard, Citi, and BlackRock's leadership in CSR, the impact of the pandemic on accelerating CSR, the challenges of raising VC capital as a woman and as a social impact co., and what it's like to pitch President Obama & being on the front page of the NYTimes.Goodworld helps companies grow by making it easy to embed Social Impact into commerce, workplace culture and sustainability initiatives. Through our Social Impact experiences, sales...2022-08-0237 min
Between Two COO's with Michael KoenigBolster EVP, fmr Makerbot CEO & Techstars COO&CIO, Jenny Lawton on Makerbot's $400M exit, running one of the world's most successful seed fund & accelerator, Montessori framework in business, her advice to my daughters & moreJenny Lawton is the EVP at Bolster, an on-demand executive talent marketplace that helps accelerate companies’ growth by connecting them with experienced, highly vetted executives for interim, fractional, advisory, project-based, or board roles. Prior to Bolster, Jenny served in a variety of C-Suite roles which include her time as the Chief Strategy Officer and then CEO of MakerBot, the leader in desktop 3D printing technology that was acquired by Stratasys for over $400M. Jenny also served as the COO of LittleBits, the STEM learning division of Sphero (the company behind the adorable droid BB8 that captured our hearts in the...2022-06-1445 min
Between Two COO's with Michael KoenigHandshake COO, Jonathan Stull on democratizing access to opportunity, the journey to $100M ARR & a $3.5B valuation, building a three-sided marketplace, timing, global expansion, adding independent board members, the move to hiring specialists, and moreHandshake COO, Jonathan Stull, joins to talk about the journey of building a three-sided marketplace to $100M ARR at a $3.5B valuation with over 500 employees. We touch on the role of COO at Handshake; Jonathan's path from waiting tables to Capital Hill to PE to tech; compromising on tactics but not on vision or mission; adding independent board members; deploying $100MMs in funding; the move from hiring generalists to specialists; global expansion; timing and more.Handshake’s mission is to democratize access to opportunity: to help every student find the right job, no matter where they’re from...2022-06-0153 min
Between Two COO's with Michael KoenigGoGuardian COO, Cyrus Mistry, on joining at the same time as $200M in new funding, switching from Google to a startup, how SaaS ops are different than Disney ops, bringing millions of bricked Chromebooks back to life from a cruise shipGoGuardian COO, Cyrus Mistry, spent 14 years at Google as the Director of Product Management for Chromebooks bringing computers to schools, before joining GoGuardian as COO right when they raised $200M in new funding from Tiger Global Management. Cyrus has a wealth of knowledge not only stemming from his four advanced degrees but also from his operating experience at Disney prior to Google. Have a listen to hear about his story and what it's like to move from Google to a startup.Cyrus Mistry on LinkedIn: https://www.linkedin.com/in/cmistryGoGuardian: https://www.goguardian...2022-05-0229 min
Between Two COO's with Michael KoenigPeople.ai COO, Art Harding, on Supporting Ukrainian Team Members, E2T: Driving Efficiency, Effectiveness, & Transformation, Translating Chaos & Ambiguity into Structure, How Great Operating Leaders Think Like Project Managers, & MoreArt Harding is the COO at People.ai, and joins to share how People.ai has supported their Ukrainian team members, how coaching is inspiring for the right to inspect performance and provide timely and meaningful feedback, the operational mandate of E2T: driving efficiency, effectiveness, and transformation, how COO is the most interesting job in the world, launching new products, what healthy friction looks like, how great operations leaders think like project managers, and product and sales lead grow. Art Harding on LinkedIn: https://linkedin.com/in/arhardingPeople.ai: https://people.ai...2022-04-1146 min
Between Two COO's with Michael KoenigUplight COO & fmr Symantec CSO, Angela Tucci on Reaching a $1.5B Valuation in 3 Years, Business as a Force for Good, B Corps, Reducing Carbon Emissions, Merging 6 Companies, and How Diversity Creates SafetyAngela Tucci, COO at Uplight, joins to talk about running a $1.5B company created from the M&A of 6 companies, advocating for voice & equity for women in the workforce, finding an inspiring CEO, working with utility companies to reduce their carbon footprint, taking private equity vs. VC funding, integrating acquisitions remotely during covid, the impact of politics, and systems thinking.Prior to Uplight, Angela was Chief Strategy Officer at Symantec, Chief Revenue Officer and Chief Marketing Officer at Rally Software, and Chief Executive Officer at Apto, so she's a clear underachiever. :)Uplight is a technology...2022-03-1749 min
Between Two COO's with Michael KoenigFrom the White House to a $20B IPO, Hiptrain COO & fmr Lyft Exec, Steve Taylor, on Managing a $500M P&L, the Why Behind the Pink Mustaches, Making the Analog Digital, Global Labor Arbitrage, & 3 ExitsSteve Taylor is an operating executive with experience building high-performing teams and scaling high-growth, category-defining companies. After spending the early part of his career flying E-2C Hawkeyes in the US Navy, he received a Masters of Policy Management from Georgetown University and spent five years as a management consultant. Steve joined Lyft in 2015 with just 220 employees, led two of the company's largest territories, launched multiple product lines, and managed a P&L with >$500M in annual revenue as we grew to 5,500 employees and a $20B IPO. In 2020, as COO at Fixt, with just 20 employees and $6M raised, he...2022-03-0335 min
Between Two COO's with Michael KoenigKettle COO, & White House Innovation, Nathaniel Manning on Balancing Risk In A Changing Climate, Structure Without Bureaucracy, Evolution By Design, Good Decision Making, the Social Contract of Insurance, and Sitting on a Monastery Cushion for 3 MonthsKettle COO, Nathaniel Manning, talks about balancing risk in a changing climate, structure without bureaucracy, evolution by design, good decision making, the social contract of insurance, and sitting on a monastery cushion for 3 months. He also talks about old guard vs new guard, building the plane while it's flying, making the implicit explicit, and evolution by design.Nathaniel has a long career of founding and leading companies including Fellow Robots, BRCK, the largest provider of public wifi in Africa, and Ushahidi the world’s largest open-source platform for crisis response. Along the way, he worked on furthering cl...2022-02-1547 min
Between Two COO's with Michael KoenigHatch COO, Dave Weiss, on Selling 2 Million IoT Devices, Cofounding a Company with His Wife, Shark Tank to VC Funding, Moving From CTO to COO, and Visiting Customers' HomesDave Weiss, co-founder, and COO of Hatch, joins us to discuss what it takes to confound a hardware company with his wife, sell 2 million IoT devices, the heightened consumer expectations of hardware, visit customers' homes, going from Shark Tank to VC fundraising, moving from CTO at BabyCenter to COO, and believing in wet paint.Prior to co-founding Hatch, Dave was the CTO of BabyCenter, where he was responsible for software engineering and product. Dave Weiss on LinkedIn: https://www.linkedin.com/in/daveweiss99Hatch: https://www.hatch.coMichael Koenig on L...2022-02-0833 min
Between Two COO's with Michael KoenigPart 1: Catherine Stewart on Scaling Operations and People Management at Shippo and AutomatticCatherine Stewart is the former Chief Operating Officer at Shippo and Chief Business Officer at Automattic (WordPress), joins us in part one of a special two-parter, to talk about the craft of scaling operations at hyper-growth tech companies. Topics include shifting strategic priorities at Automattic to also focus on revenue generation and e-commerce through the acquisition of WooCommerce, the shift from Facebook to Automattic, balancing the entrepreneurial mindset with the need for processes, not sugar-coating it, and why her time at Random House yielded some of the most valuable learnings of her career.Part two, coming next m...2022-01-1943 min
Between Two COO's with Michael KoenigPart 2: Grafana Labs COO, Doug Hanna on Scaling the Go-To-Market Machine of a $3B Tech CompanyDoug Hanna, COO at Grafana Labs, joins us to discuss scaling a company to $3B in valuation after raising $330M in funding. As a former Zendesk VP of Ops, Doug has had front seats at both companies, during hyper-growth. This episode, Part 2, focuses on scaling the go-to-market machine of a multi-billion dollar company. Grafana Labs is the company behind the lead open source observability platform, Grafana, used by the likes of Salesforce, Paypal, Verizon, Ebay, and 750K other instances.Part 1 of Doug's session dropped on January 4th, 2022 and focuses on Doug's path to COO and scaling people...2022-01-1142 min
Between Two COO's with Michael KoenigPart 1: Grafana Labs COO, Doug Hanna On Building a $3B Company with Open Source, Scaling Culture and Going From 70 to 500 PeopleDoug Hanna, COO at Grafana Labs, joins us to discuss scaling a company to $3B in valuation after raising $330M in funding. As a former Zendesk VP of Ops, Doug has had front seats at both companies, during hyper-growth. This episode, Part 1, focuses on people and culture: what goes into scaling from 70 to 400 net new employees in a mere 18 months. Grafana Labs is the company behind the lead open source observability platform, Grafana, used by the likes of Salesforce, Paypal, Verizon, Ebay, and 750K other instances.Part 2 of Doug's episode will air in a few weeks and...2022-01-0422 min
Between Two COO's with Michael KoenigNira COO, Marie Prokopets on Pivoting From Search to Security, Context Switching, Balancing Risk, and BreathingAfter doing $26B of M&A at Diageo, Marie Prokopets joined the startup world, and together with Hiten Shah, founded Nira.com a way to secure your company documents and access controls. As COO at Nira, Marie joins us to talk about pivoting from search to security, context switching, and what happens when vendors mess up access controls.Nira.com Marie Prokopets on Twitter: https://twitter.com/MarieProkopetsMarie Prokopets on LinkedIn: https://www.linkedin.com/in/marieprokopetsHiten Shah on Twitter: https://twitter.com/hnshahMichael Koenig on L...2021-12-1425 min
Between Two COO's with Michael KoenigTucows Chief Product Officer, Justin Reilly, on How Product Design Influences Operations and Where AI Fits In, Ting's Amazing Customer Care, and Photos Almost Pushing a LaunchTucows Chief Product Officer, Justin Reilly, joins as our first non-COO, and shares on your customer's best last experience, how product design influences operations and where AI fits, Ting's amazing customer care, and how photos almost pushed a launch.Justin focuses on building the next generation of consumer products, particularly where AI meets customer experience. Prior to Tucows, Justin was Head of Product & CX Innovation at Verizon. He founded Focus Health, Grey Seven Labs, and Qstir. He was a Director of Strategy and Experience at Macquarium, lead the Strategy and Innovation team at Arke Systems. He currently...2021-12-0635 min
Between Two COO's with Michael KoenigTrue Ventures COO, Jim Stewart, on Taking Four Companies Public, Venture Capital Firm Operations, Keeping a Cool Head, and Export ControlsTrue Ventures Chief Operating Officer, Jim Stewart, on what it's like to take four companies public, what goes into the operations to run a venture capital firm, how to take calculated risks, and what to do when you realize that you've just violated US government export controls when you're doing an IPO roadshow (don't panic).True Ventures is a venture capital firm with an astonishing track record of investing in the best companies like Peleton, Fitbit, Ring, Duo Security, Automattic, and Sweetgreen, which just went public on the New York Stock Exchange.Jim initially joined...2021-11-2926 min
Between Two COO's with Michael KoenigAllie Fleder, COO at SimplyWise on Changing Industries, How COO Roles Vary, Remote as an Extrovert, Clarity at Early Stage Startups, and Head WoundsAllie Fleder is the cofounder and COO of SimplyWise, an NYC-based fintech app helping Americans take control of their data. She previously founded and ran Sherpa, a British luggage delivery platform for busy travelers that was acquired in 2019. Before starting her own business, she consulted for VC-backed fintech and travel tech startups in London and NYC. She Chairs EUROUT, Europe’s largest LGBT+ business conference, and serves on the Digital Corps leadership committee of Out in Tech. Allie is a graduate of Columbia University and London Business School, where she received a full scholarship. Check out:A...2021-11-2128 min
Between Two COO's with Michael KoenigDeepak Chopra Global COO, Rich Wallach, on synchrodestiny, managing through uncertainty, and remote operationsRich Wallach, COO, and CFO of Deepak Chopra's Chopra Global, joins us to discuss:How a philosophy degree prepared him for everything and nothing at the same timeCredit Suisse's attempt to crush the humanity out of himCreating security, safety, and certainty for employeesOver-communicating without stressing people outHow processes can improve peopleGetting rid of the office and going fully remoteAnd lemurs. Yes, lemurs, the animals.Chopra Global: https://chopra.comChopra Global's Brand New Mobile App: https://chopra.com/appChopra Global's Upcoming Events: https://chopra.com/retreatsRich Wallach on LinkedIn...2021-11-2144 min
Between Two COO's with Michael KoenigIntroducing Between Two COO'sBetween Two COO's: www.betweentwocoos.comMichael Koenig: https://linkedin.com/in/mkoenig514
2021-11-1801 min