Brad Feld On The Emotional Operating System of Great Leaders and Giving First

Get 90 days of Fellow free at Fellow.ai/coo In this episode, Michael Koenig speaks with Greg Keller, co-founder and CTO of JumpCloud, about identity access management and why it’s becoming one of the most important operational systems in the age of AI. Greg explains how traditional identity systems were designed for office-based companies running Microsoft infrastructure and why that model broke as companies moved to SaaS, cloud infrastructure, and remote work. The discussion then turns to the next big shift: the rise of AI agents and synthetic identities inside organizations. As companies deploy more AI tools, the number of machine identities may soon outnumber human employees. Managing what those systems can access will become a critical security and operational challenge.   Topics Covered What a CTO actually does Greg explains the different types of CTO roles and how technology leaders help companies anticipate where the market is headed. Identity Access Management explained simply IAM answers three core questions inside every company: Who are you? What can you access? How is that access managed?   Why the old IT model broke Traditional identity systems were built for on-premise offices and Microsoft infrastructure. Modern companies now operate across: SaaS applications cloud infrastructure remote work environments multiple operating systems How JumpCloud approaches identity JumpCloud was built to manage identity across devices, applications, and infrastructure regardless of platform. Where Okta fits in the ecosystem Okta helped modernize browser-based authentication through Single Sign-On, while JumpCloud focuses on broader identity infrastructure.   AI, Security, and Synthetic Identities Why COOs should push AI adoption Greg argues AI adoption is no longer optional. Companies must encourage teams to improve productivity and efficiency using AI.   The rise of synthetic identities AI agents, bots, APIs, and service accounts are becoming new actors inside companies that require identity governance.   Bots may soon outnumber employees Organizations will soon manage more machine identities than human ones.   AI as a potential insider threat AI systems can become security risks if they are granted excessive permissions or misinterpret policies.   The API key governance problem Many AI integrations rely on API keys, which are often poorly managed and can create hidden security risks.   Key Takeaway As companies adopt AI, identity access management becomes the control layer that determines what both humans and machines are allowed to do inside the organization. The companies that manage identity well will move faster and operate more securely.   Links: Michael on LinkedIn: https://linkedin.com/in/michael-koenig514 Greg on LinkedIn: https://www.linkedin.com/in/gregorykeller/ JumpCloud: https://jumpcloud.com/ Between Two COO’s: https://betweentwocoos.com Episode Link: https://betweentwocoos.com/ai-agents-identity-access-greg-keller

Get 90 Days of Fellow's incredible AI notetaker for free at fellow.ai/cooGuest: Seth LevineBook: Capital EvolutionPodcast: Between Two COOsHost: Michael KoenigWhat we coverWhy Seth wrote Capital Evolution and why nowWhy today’s economic shift is structural, not cyclicalHow power has moved from public institutions to businessesWhat companies are being asked to carry that they weren’t built forHow AI fits into this broader realignmentEarly signals that companies are adapting well to AIWhat strong executive teams do differently during uncertaintyCommon leadership traps when change happens too fastA real crisis from a portfolio company and what the executive team did wellThe new leadership muscle operators need for the next decadeEpisode Chapters / Timestamps00:00 – Introduction01:40 – Seth’s 30-second pitch for Capital Evolution04:05 – Why this shift is structural, not cyclical07:20 – What’s broken in the current economic model11:00 – The power shift from government to business15:10 – What leaders are quietly losing18:45 – Where AI fits into this realignment23:30 – What boards see when AI adoption works28:05 – How strong executive teams handle uncertainty33:40 – Leadership traps during rapid change38:10 – A crisis inside a portfolio company44:00 – The new muscle operators must build48:50 – A moment Seth never thought he’d see

Get Brad's new book, Give First.00:00 — Cold open: “Something new is fucked up in my world every day”02:00 — The Yoda t-shirt story + the mythology of Brad Feld04:00 — “Give First” vs. “Pay it Forward”: philosophy, not obligation07:00 — Why giving isn’t altruism — and how it works in complex systems10:00 — Positive-sum vs. zero-sum: tennis, trust, and long games13:00 — Does giving create outcomes, or just energy?16:00 — Why Brad writes books: longform thinking as meaning-making20:00 — Searching for meaning through mentorship and reflection23:00 — “I hate the phrase pattern recognition” — mentorship done right28:00 — The power dynamic between founders and mentors32:00 — Management through commitment, not control35:00 — Agile as an operating system for accountability38:00 — Emotional intelligence and the role of executive coaches41:00 — Mentor vs. coach vs. therapist vs. advisor45:00 — Trust as the foundation of all high-leverage relationships47:30 — Wild story: when the second floor of Sphero’s building collapsed52:00 — “They can’t kill you and they can’t eat you” – Len Fassler’s advice55:00 — Closing thoughts on being the Bill Murray of venture capital

This episode goes deep into the mechanics of scaling a company from steady growth to breakout velocity. Peter shares how Spreedly quadrupled ARR growth in his first year without increasing OPEX, why the “right people pointed at the right problems” is everything, and how to decide which problems are existential versus learn-as-you-go.We dissect how go-to-market organizations evolve from $20M to $100M ARR, the power of focus and role separation, and how to keep silos aligned around one customer story.Peter also explains the shift from “payments orchestration” to “open payments” and how Spreedly’s position as the original player in the space gives them unique leverage. We walk through the future of agentic commerce, Google’s new agent-to-agent payments protocol, and what it means when agents can transact faster than any human could ever shop.We close out with the Dodgeball acquisition, a primer on fraud orchestration, and a wild story about working an entire night shift at a nightclub during a meltdown launch.Topics Covered:How Peter defines the journey to presidencyThe “right person, right problem” frameworkOne-way vs two-way doors for staffing big problemsHow to scale a GTM org from $20M to $100MWhy open payments replaces orchestrationSpreedly’s unique market position and 15-year head startAgent to agent commerce and Google’s new payments protocolHow AI changes the velocity of money movementFraud orchestration and Spreedly’s acquisition of DodgeballBalancing profitable growth vs growth at all costsPerception vs reality in leadershipPeter’s wildest “I never thought I’d see that” story 

Get 90 Days of Fellow's AI Meeting Assistant FREE at fellow.ai/coo This week on Between Two COOs, Michael sits down with Harris Clarke, COO at GuideCX, to talk about what steady leadership actually looks like inside fast-changing companies.Harris started his career in protocol and operations for the U.S. Department of State, where “process” wasn’t just a buzzword — it was survival. He shares how those lessons translate to running a modern SaaS organization and why purpose, process, and payoff are the anchors of any good meeting.They dig into:How government discipline shaped Harris’s operating styleThe “three P’s” framework for productive meetingsWhy decision speed is overrated — and what Harris means by “Did anyone die or go to jail?”What he learned from executive coaching and board feedbackHow GuideCX built a new product category around customer onboardingHow AI is quietly reshaping how he manages teams and prepares communicationsWhy calm is a competitive advantage during crisis moments like SVBMichael also gives context at the top: this episode was recorded across two sessions, after a recording issue mid-interview (and yes, he’s now officially a Riverside convert).It’s a conversation about building trust, running tight systems, and keeping your head when everything around you is changing.Harris Clarke on LinkedInGuideCXMichael Koenig on LinkedInBetween Two COO's WebsiteEpisode Website 

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. Timestamps00:00 – Intro & sponsor01:00 – The chaos of Superstorm Sandy02:00 – Anna’s journey: from theater to tech06:00 – The making of a generalist10:00 – Joining Cascade and fixing retention11:00 – Creating a “working rhythm”14:00 – Governance vs. red tape17:00 – The 5 pillars of strategic maturity19:00 – Turning strategy into execution24:00 – How Cascade uses AI internally28:00 – OKRs, KPIs, and strategy frameworks33:00 – Who owns strategy?36:00 – Rebuilding a business overnight43:00 – Closing thoughts Between Two COO's - https://betweentwocoos.com Episode Website - https://betweentwocoos.com/anna-elwood-coo-cascadeAnna Elwood on LinkedIn - https://www.linkedin.com/in/annaelwoodMichael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514 

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/cooGuest: Lance Willett, Chief Quality Officer at AutomatticTopics Covered:How Automattic’s open source culture evolved over 20 yearsWhat a Chief Quality Officer actually does—and why it mattersQuality = Craft × Context, and how that feedback loop scalesAutomattic’s AI strategy: support bots, contextual UI, and site generationThe importance of tools like Linear and Storybook in enforcing qualityHow Automattic balances speed, risk, and governance with AI experimentationLessons from stabilizing Tumblr during its post-acquisition rebootPrioritization and the dangers of unbounded optimismLeadership takeaways from working closely with Matt Mullenweg🕰️ Time Map00:00 – 03:00: Intro and Lance’s journey from freelancer to Automattic03:00 – 06:30: How Automattic’s open source ethos evolved over 20 years06:30 – 10:30: What it means to be a Chief Quality Officer—Craft × Context10:30 – 15:00: Scaling quality: repo sprawl, signal vs. noise, and auditing15:00 – 20:00: UX details like forms, performance, and speed as quality levers20:00 – 24:00: Driving culture change with standard tooling (Linear, Storybook)24:00 – 28:00: Guardrails for AI experimentation and internal governance28:00 – 32:00: AI at Automattic: support bots, contextual UI, AI site builder32:00 – 36:00: Competing with Webflow, Wix, and Squarespace through innovation36:00 – 38:30: Balancing ecosystem contribution with revenue and investor pressure38:30 – 41:00: Lessons from stabilizing Tumblr: cost, culture, safety, turnover41:00 – 44:00: Automattic’s long-term challenge: bounded optimism and focus44:00 – 46:30: Leadership wisdom from Matt Mullenweg: details always matter46:30 – 49:00: Lance’s $250K mistake—and what it taught him about leadership https://brodo.com/ (our other sponsor 😂)https://fullstackleader.blog/ (work topics: WordPress, tech, productivity, quality, & more)https://lance.blog/ (fun stuff: poems, stories, links; photos “on the go”)https://linear.app/https://clay.earth/ via https://automattic.com/2025/06/12/automattic-welcomes-clay/ Companies with dedicated quality efforts:https://anthonyhobday.com/blog/20240914.html > While fixing small bugs might not 10x your growth overnight> Not fixing them will make 10x growth impossible over timeCredit: Casey Winters – someone you should have on this show if you haven’t alreadyhttps://caseyaccidental.com/ Episode webpage - https://www.betweentwocoos.com/automattic-chief-quality-officer-lance-willett-wordpressMichael Koenig - https://linkedin.com/in/michael-koenig514 Between Two COO's - https://betweentwocoos.com 

Get 90 days of Fellow's AI meeting assistant at fellow.app/cooWhy 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 innovation — and why bad ideas are worth celebrating (29:00)Leading through operational ambiguity and defining what to say “no” to (49:00)How product thinking helps Linda prioritize and run the business (54:00)Creating an actual in-office “innovation lab” — and what worked (1:04:00)Wild story: how her team navigated the SVB collapse weekend (1:08:00) 

Get 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(10:15) How AI is changing the org chart and team design(14:00) The problem with low-context playbooks(17:45) RevOps structuring and ownership(22:00) Forecasting: visibility vs. execution(27:00) AI tooling, integration, and buyer psychology(31:00) Agent-to-agent interactions and AI futurecasting(34:30) What Doug’s watching next in ops and AI LinksDoug Hanna on LinkedIn - https://www.linkedin.com/in/douglashanna1/Kustomer - https://www.kustomer.com/Michael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514Between Two COO's - https://betweentwocoos.com 

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 judgment remains crucial.Metrics and KPIs in RevOps must directly correlate to revenue growth, profitability, and organizational efficiency.Brad emphasizes proactive disruption, transparency, and alignment to navigate the rapid evolution of sales operations.  Timestamps:(02:00) What is RevOps and how Brad transitioned into it from finance(07:00) Common misconceptions and early mistakes in RevOps(11:00) Building a robust RevOps foundation and data hygiene(15:00) Creating alignment across sales, marketing, and customer success(20:00) Key metrics and strategic decision-making in RevOps(24:00) AI’s impact on RevOps and potential pitfalls(30:00) Real-world experiences with AI-powered sales calls(33:00) RevOps vs. SalesOps and defining terms clearly(36:00) Advocating for RevOps budgets and demonstrating value(40:00) Lessons learned about effective communication and internal alignment Links:90 Days Free of Fellow's AI Meeting Assistant: https://fellow.app/cooBrad Rosen on LinkedIn: https://www.linkedin.com/in/bradrosen1/Michael Koenig on LinkedIn: https://www.linkedin.com/in/michael-koenig514/  Sales Assembly: https://www.salesassembly.com/Between Two COO's: https://betweentwocoos.com Episode URL: https://www.betweentwocoos.com/sales-assembly-president-brad-rosen-on-unlocking-growth-and-why-revops-is-critical-for-sustainable-scaling