Second in Command: The Chief Behind the Chief with Cameron Herold

What if the key to scaling your business wasn’t more people, but ruthless focus combined with relentless speed?Cameron Herold teams up with Sean Kim, the former President and Chief Product Officer at Kajabi (ex-Amazon, ex-TikTok) and the current Chief Product Officer at HighLevel, to crack open the playbook that turns chaos into proven, compounding wins. Inside this conversation: why leaders who say “no” more often grow faster, how to make data the backbone of every decision, and the real story behind powering a $1.7B creator platform without burning out your team or chasing shiny objects.Listen now to dodge the trap of feature bloat, hiring sprees, and slow, clunky execution. These are unfiltered insights and backed-up frameworks from the inside that you simply won’t get anywhere else, unapologetically blunt, deeply actionable, and designed for COOs and founders ready to scale, not just survive.Timestamped Highlights00:23 – Why Sean Kim said “hell no” to TikTok… at first. The surprising conversation that changed everything01:10 – “Discovery” is the real unlock… how it built TikTok’s domination and sparked Sean Kim’s obsession08:18 – What happens when you leave Amazon’s scale for pure startup chaos… scrappy desks, no process, and surviving the LA office09:24 – The secret power of the “doc writing” culture… how writing, not slides, became TikTok and Amazon’s unfair advantage12:24 – Ruthless speed… fail fast, double down faster, and outmaneuver every competitor. This is how TikTok really operates14:45 – Why Kajabi never bloats its teams… and how knowing exactly when to hire is a massive competitive edge17:13 – The impact calculator… predicting revenue, retention, and customer wins before a single feature ships25:40 – How to crush “feature creep” and avoid turning your SaaS into a Frankenstein’s monsterAbout the GuestSean Kim was previously the President and Chief Product Officer of Kajabi, the all-in-one platform powering $1.7B+ in annual creator revenue. He previously led product teams at TikTok and Amazon Prime, shaping global growth strategies and a customer-obsessed culture. With a reputation for world-class execution and a bold, systems-driven mindset, Sean stands out as a top operator for scale-minded founders and COOs. He is currently the Chief Product Officer at HighLevel.🔗 LinkedIn Mentioned ResourcesTikTokAmazon PrimeBulletproof CoffeeDave AspreyByteDanceThe “doc writing” process (Amazon framework)Impact calculator for product decisionsImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiNote: This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside.The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Ever wonder why some COOs quietly double revenue while others burn out cleaning up someone else’s mess?Cameron Herold unpacks the “second in command” reality with Rick Marini, serial entrepreneur, private equity veteran, and former COO powerhouse at iconic brands like Grindr. They dive into the realities most leaders dodge: gutting toxic teams, the cost of misaligned culture, and the real career advantage of NOT being CEO. You’ll get the battle-tested playbook for earning team trust, breaking through stagnant growth, and building companies where A-players fight to stay.Miss this episode, and you risk leading a team that resents you, losing your top talent, or—worse—sleepwalking into irrelevance while your competition surges ahead. Listen now before your window to upgrade your influence and execution closes. This is unfiltered COO intelligence you won’t find anywhere else.Timestamped Highlights15:05 – How do you fix a company doing $100M with a 1.8-star Glassdoor? The turnaround playbook starts here.17:15 – Three straight owners, one legendary LGBTQ brand: The wild truth about trust-building at Grindr20:08 – Held hostage for a million? Why Rick Marini and team had to moderate user content—and what it taught the company21:04 – The one line that made an exec break down in the NYSE lobby, and how you really know your team would run through walls for you25:16 – A-players vs. B-players: The uncomfortable signs you’re settling, and how to actually spot (and hire) difference-makers31:08 – Do you really have the right COO? How private equity calls BS on CEO/COO dynamics42:00 – With AI moving this fast, how do you NOT get blindsided? The war room approach to offense vs. defense46:06 – Mentorship, “work from home,” and why Gen Z will lap you if you hide behind ZoomAbout the GuestRick Marini is the Co-Founder and Managing Partner of Catapult Capital and the Co-Founder, President and COO of Rails, and a renowned operator, investor, and board leader with over 25 years scaling and transforming businesses. Previously CEO/COO at Grindr and Rails, Rick specializes in high-stakes turnarounds, talent strategy, and innovative culture design for tech and consumer brands.🔗 LinkedIn | WebsiteMentioned ResourcesRailsTickleHarvard Business SchoolJames CurrierGlassdoorTinderAugust CapitalYPOHamptonSam ParrSean MagennisMy First Million (podcast)Montreal (Grinder Restaurant)BumbleGino Wickman’s “Traction”Taps (movie)Committee on Foreign Investment in the United States (CFIUS)TikTokNew York Stock ExchangeImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.Sponsored by:Redirect Health - Affordable healthcare benefits designed to make traditional insurance optional, with 24/7 access to primary care and Rx support that helps businesses reduce costs while keeping employees covered.Learn more: https://www.redirecthealth.com/

Ever feel like you’re drowning in urgent tasks and legacy processes, wondering how real COOs actually turn chaos into clarity?Meet Arnold le Rutte, COO of The Virtual Hub, COO Alliance member and bronze partner, who went from retail entrepreneur to running the nerve center of a 300+ strong offshore team. Together with our new podcast co-host Lindsay Smith - appearing in her first episode in the co-host role - they pull the curtain back on ruthless prioritization, AI survival strategies, and the misunderstood art of building bulletproof, scalable systems that actually unlock human potential. No corporate platitudes, just real stories on managing explosive turnover, navigating the tricky CEO handoff, and how the best operators weaponize client-side empathy.Listen now, or risk drowning in the overwhelm that kills too many leaders. These are insights you will not find on LinkedIn, and you’ll wish you’d heard them before your next hire, your next pivot, or your next fire to put out.Timestamped Highlights01:19 – The pizza delivery gig that rewired Arnold le Rutte’s approach to problem-solving (and what it means for COOs today)03:32 – What really happens inside a 100+ person offshore operation and why most clients completely miss the point06:39 – Bittersweet business: when growth isn’t enough, and the turning point that led to a radical career shift11:23 – The game-changing realization about SME clients that upended The Virtual Hub’s business model15:41 – How to blow up burnout: Supporting teams, slicing admin, and warning signs leaders mess up21:55 – The AI smokescreen: Why true capacity-building is about brains, not bots26:58 – The one question every client gets wrong about outsourcing and how Arnold le Rutte reframes it for explosive leverage44:31 – Undercover boss confessions: The invisible complexity behind every “simple” successAbout the GuestArnold le Rutte is COO of The Virtual Hub, a COO Alliance member and bronze partner, and a powerhouse operations executive and former founder who scaled retail and wholesale businesses before taking the reins at one of the world’s leading offshore virtual professional firms. Known for blending client empathy with brutal operational clarity, he transforms complex, people-centric businesses by driving process, deep tech adoption, and relentless culture-building across borders.🔗 LinkedIn | WebsiteMentioned ResourcesVancouver and Boston COO eventsBarbara TurleyAsana (software)About the Co-HostLindsay Smith is an experience-driven growth strategist and former Chief Strategy Officer. This marks her first episode as official co-host of the podcast. She previously scaled a new region without a traditional sales team or bloated marketing budget by turning relationships, culture, and execution into revenue. She is the author of No One Needs Another Company Mug. Stop Branding. Start Experiencing and helps leadership teams use experience as a competitive growth lever.🔗 Connect with Lindsay on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Lindsay Smith. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

What would happen if you finally ditched micromanagement and actually let your teams run wild, faster, riskier, and more creative than you’d ever dare on your own?Ben Plomion, COO of Pearl AI, joins Sivana Brewer for a sharp, no-fluff deep dive into the gritty reality of leading in markets where mistakes happen fast and growth is non-negotiable. Drawing from cross-functional battle scars in marketing, ops, and tech, Ben unpacks how he leveraged his CMO chops to become a next-level COO, why most leaders fail at “connecting the dots,” and exactly how he’s turning AI into his secret weapon for culture and operational scale.If you’re tired of theory and ready for the untold COO playbook that frees you from indecision, protects you from hidden traps, and gives you unfair access to what the best operator-leaders are actually doing, listen now. Stalling means losing team trust, missing radical growth, and getting left behind.Timestamped Highlights[00:03:42] – The shocking “dumpster” pitch that clinched Ben’s COO job—would you take this text?[00:05:10] – Connect the dots or die: Why leaders who only skim the surface always lose big[00:07:26] – Zero in-house finance, outsourced chaos—how Ben plugged the leaks before it was too late[00:10:51] – From chief cook to master delegator: The brutal art of giving up “employee benefits” and focusing where it matters[00:14:42] – CEO second-in-command: The secret archetypes and why most COOs get it wrong[00:18:29] – CMO to COO crossover: The superpowers that every operator should steal from marketing[00:21:23] – Ditching values for operating principles—radical new rules for building a creative, AI-savvy team[00:32:19] – “Let them run”: The unorthodox motto that keeps Ben’s teams breaking the rules, beating churn, and staying aheadAbout the GuestWith over two decades of experience in marketing, commercial and operational leadership across Artificial Intelligence, Computer Vision, and Blockchain, Ben Plomion is the Chief Operating Officer at Pearl—the leading AI Software-as-a-Service (SaaS) company in dentistry. Prior to Pearl, he served as Chief Marketing Officer at Dibbs, an Amazon-backed tokenization-as-a-service (TaaS) platform. He was previously Chief Growth & Marketing Officer at GumGum, where he played a pivotal role in advancing AI-driven contextual advertising. Earlier in his career, Ben led global digital media efforts at both Magnite and GE Capital. A Forbes contributor and trusted advisor to companies like Deanna.ai, PebblePost, and #Paid, he is also a committed educator in the realms of AI, marketing, and Web3.🔗 LinkedIn | WebsiteMentioned ResourcesGumGumAnthropic ClaudeChatGPTHubSpotGoogle DriveOKR (Objectives & Key Results)Amazon “70% data principle”Get Scalable by Ryan DeissAbout the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.Sponsored byNext Level Growth - A proven system designed to help entrepreneurs scale their businesses with clarity, accountability, and the right strategic support to reach their next stage of growth.Learn more: https://www.nextlevelgrowth.com/

Ever felt like your company is running in circles while you quietly burn out, stuck between drive and exhaustion?This episode is a blunt, emotionally raw exploration with Lindsay Gibson, COO of TextNow, a leader who’s walked away from the grind, returned for redemption, and rebuilt both companies and herself from the inside out. Sivana Brewer dives deep with Lindsay into the shock of losing vision, the chaos of remote work, and the brutal clarity that comes only after you’ve crashed headlong into career “success.”If you’re tired of vague leadership advice and want exclusive, no-BS strategies for authentic leadership, unclenching burnout’s grip, and making culture work for real teams, listen right now. Miss this, and you might repeat the pain Lindsay barely escaped. These lessons are battle-forged, urgent, and unlike anything the standard playbooks offer.Timestamped Highlights[00:01:11] – The brilliant but gritty origin of TextNow: solving real pain for people who have to choose between a phone bill and groceries[00:02:45] – Why Lindsay left her COO seat (twice) and what chasing “interesting work” really costs[00:04:34] – The BlackBerry “return rate” disaster: how fixing buyer’s remorse became a master class in real-world delegation[00:07:49] – The shocking truth: Engineering wasn’t the problem—here’s what really derails a company’s goals[00:10:11] – The brutal downside of remote-first culture… and the hardest part of rebuilding accountability across a fractured team[00:14:32] – Motherhood, loss, and the hidden price of ambition: Lindsay’s real talk on the boundaries she’ll never break again[00:19:04] – “Dead bodies in the process”—when leadership feedback stings and the rebirth of authentic management[00:27:54] – Why remote teams lose their soul (and how one-on-one connection fights back against isolation)About the GuestLindsay Gibson is the Chief Operating Officer of TextNow, a disruptive, ad-supported mobile carrier serving millions who demand true flexibility in mobile communications. With over two decades shaping iconic tech cultures, including a 16-year run at BlackBerry, she’s mastered the hard edge of scaling, comeback leadership, and authentic team connection. Known for leading through crisis and comeback, Lindsay is a straight-talker driven by integrity and obsession with growth.🔗 LinkedIn | WebsiteMentioned ResourcesBlackBerryChatGPTCursorReclaimT-MobileAT&T“Burnout” (book)About the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Ever secretly wondered if success, early retirement, a big exit, and the CEO chair are as good as it looks? What if the “dream” of ownership leaves you restless, searching for meaning, and itching to build again?This episode pulls back the curtain on the real journey: Marcus Hantla, a relentless builder who’s seen both sides, reveals the wild emotional highs of exits and the raw, daily grind of COO life inside Contractor Foreman, a fast-growing SMB construction SaaS. He and Sivana get blunt about AI hype, hands-dirty delegation, and the gut-check moments that test even the toughest operators.The stakes: Stop winging it in your own career, team, or transformation or risk getting left behind. Listen now to confront the myths of growth, find new ways to thrive, and get the gritty, exclusive playbook you won’t hear in sanitized TED Talks.Timestamped Highlights03:41 – What no one warns you about early retirement and the uncomfortable truth about waking up “free.”06:43 – How a random plumber changed Marcus’s entire career (on his very own porch).09:10 – The COO/CEO “deciding dance” and why true empathy is a secret growth weapon.14:40 – Real talk: Losing a debate with the CEO (and why not every “brilliant” idea should win).17:25 – AI sales calls, live demos vs. real humans—what actually works right now.20:55 – Is the “beautiful” user interface dead? Why the next SaaS war is about simplicity, not design.26:14 – The dangerous side of AI consensus: Can chasing “truth” kill the next big breakthrough?35:03 – The sobering math of executive gratitude (and the crisis no leadership manual covers).About the GuestMarcus Hantla is the COO of Contractor Foreman, a leading construction management software platform engineered for small and mid-market builders and contractors. With 25+ years in construction and tech—plus multiple exits—Marcus is renowned for his hands-on leadership and hard-won insights at the intersection of trades, SaaS, and rapid growth.🔗 LinkedIn | WebsiteMentioned ResourcesCetdigitAsk the Foreman (Contractor Foreman feature)GoogleChatGPTRedditFacebookGiftology by John RuhlinSlackAbout the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.Sponsored by:Genius Network - An exclusive community for highly successful entrepreneurs, connecting you with top-tier leaders, strategic insights, and powerful relationships to help you grow your business faster and smarter.Learn more: https://www.geniusnetwork.com/

What if the single greatest unlock for scaling your company has nothing to do with strategy, and everything to do with how much you care?In this gut-level conversation, Sivana Brewer sits down with Amit Shah, COO of Virta Health, a company on a mission to reverse metabolic disease in a billion people. They reveal the raw mechanics, hard decisions, and emotional realities of building a culture where real feedback, personal mission, and relentless impact actually drive bottom-line results. Expect stories that challenge your comfort zone, a blueprint for turning skeptics into true believers, and a rare glimpse into what makes teams (and COOs) last a decade or more through hyper-growth.If you’re tired of surface-level advice and want the proven, exclusive tools to protect your culture (and your soul) as you scale, hit play now. The risk of mediocre leadership has never been higher, and these lessons simply can’t wait.Timestamped Highlights[00:00] – The rebel truth about why people don’t care what you know until something shocking happens[00:03:23] – Inside Virta’s billion-person mission and the radical evidence that built unwavering belief[00:06:57] – The jeans, Disneyland, and moment a clinical trial changed thousands of lives[00:13:17] – The single conversation that blew away a hardened healthcare skeptic[00:17:13] – Why LIVE patient stories kick off every company meeting and what that does to culture[00:21:24] – How Virta built a team that actually sticks (and outgrows their own roles)[00:25:41] – When your job changes every 12 months: The hidden playbook for surviving hyper-growth[00:33:24] – The care vs. candor tightrope—how to love your team while pushing for relentless resultsAbout the GuestAmit Shah is the Chief Operating Officer of Virta Health, where he leads growth, product development, and patient care delivery for a hyper-growth company that’s transforming metabolic disease care. With a track record spanning executive roles at Paladina Health, McKinsey, and Amazon, plus roots as a mission-driven entrepreneur, Amit is known for building high-performance teams that scale with heart and precision.🔗 LinkedIn | WebsiteMentioned ResourcesTruliaZillowDr. Steve FinneyDr. Jeff VolekDr. HallbergUnited AirlinesUS FoodsBlue Shield of CaliforniaAlex & Layla HormoziGoogle Docs, Google Sheets, Google CalendarAbout the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Ever feel overwhelmed by growth or haunted by the worry that your team’s success might derail the mission?This is your inside pass. Sivana Brewer dives deep with Dan Murphy, COO of D1 Training, to uncover what really separates winning brands from chaotic burnout. From scaling a nationwide fitness franchise by 100+ units fast, to building a culture where passion crushes bureaucracy, and tough metrics make or break careers, this episode exposes the choices, pivots, and vulnerable moments every top operator faces.Listen now if you want to avoid stalling your company’s growth, escape the COO loneliness trap, and get proven, unconventional takeaways on reinventing your playbook in a frantic market. This is real talk you won’t find anywhere else, straight from the second in command.Timestamped Highlights[00:01:01] – The wild origin story: Losing a pro career, the CEO’s game-changing invention, and how it launched a new franchise model[00:03:39] – Why D1 threw out the playbook and planted flags everywhere plus what they learned scaling from 1 to 160 locations[00:05:17] – The counterintuitive “avatar” that drives most revenue and why it’s probably NOT who you think[00:09:57] – How the right “spark” can reveal your company’s true North—advice for COOs looking for their next big thing[00:13:37] – The brutal scale-up pivot: When to walk away from side businesses, passive owners… and old friends[00:16:11] – Outsourcing secrets, bringing it all back in-house, and the moment when cost control meets franchisee happiness[00:21:28] – The biggest “aha” that changed their growth trajectory—what actually gets local buyers to care and buy in[00:25:34] – When loyalty isn’t enough: Handling hard conversations with passionate, under-performing leaders[00:27:48] – Managing egos, CEO/COO conflict, and why “freedom to dream” requires radical focusAbout the GuestDan Murphy is the Chief Operating Officer of D1 Training, a national franchise leading the youth and community athletic training space. A former Division I soccer player and West Point graduate, Dan has decades of leadership experience spanning military and high-growth franchise operations. He’s known for his relentless execution, passion-driven leadership style, and community-building expertise helping D1 scale from a single Nashville gym to 160+ locations and counting.🔗 LinkedIn | WebsiteMentioned ResourcesWill BartholomewPeyton ManningTim TebowChris PaulExosCrossFitRay Dalio’s “Principles”About the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.Sponsored by:Redirect Health - Affordable healthcare benefits designed to make traditional insurance optional, with 24/7 access to primary care and Rx support that helps businesses reduce costs while keeping employees covered.Learn more: https://www.redirecthealth.com/

Ever question if you’re truly moving the needle in a high-stakes, fast-growth role or just treading water in chaos?In this unfiltered replay, Cameron Herold gets radically real with Asana’s COO, Anne Raimondi, a powerhouse operator with a track record scaling iconic SaaS brands from eBay to Zendesk. Their candid conversation delivers hard-hitting truths and breakthrough strategies for COOs, VPs of Ops, and ambitious seconds-in-command. From conquering boardroom friction to onboarding at scale, and from navigating imposter syndrome to wielding conscious leadership, this episode is your no-nonsense roadmap to building culture, resilience, and runaway growth.The window for operational greatness closes quickly. Don’t risk getting left behind as your competitors dial in these proven systems. Press play now for a front-row seat to rare, real-world tactics you won’t hear anywhere else.Timestamped Highlights[00:00] – Why this Asana episode is a record-breaking, fan-favorite comeback[00:03:02] – The one skill that built Anne’s “uncommon” career and why she doubled down on curiosity[00:05:33] – A dot-com crash, a diamond startup, and how obsession with customer pain points kept Anne in the tech arena[00:07:47] – Is product obsession really the COO’s unfair advantage? Anne reveals what sets true ops leaders apart[00:13:14] – How Anne’s onboarding at Asana destroyed all her old assumptions about exec transitions[00:15:10] – The joy of “extra delights”—what most SaaS products miss about human motivation[00:25:34] – The real source of company politics (and how transparency kills it dead)[00:44:38] – Anne’s most vulnerable answer: How she faces down imposter syndrome and winsAbout the GuestAnne Raimondi is the Chief Operating Officer of Asana, a global leader in work management software empowering teams to orchestrate their work with clarity and impact. With 20+ years scaling technology giants, including senior roles at Zendesk, TaskRabbit, SurveyMonkey, and eBay, Anne brings deep boardroom and operational wisdom to fast-growth SaaS. She’s also a lecturer at Stanford Graduate School of Business and has served on the boards of Gusto, Patreon, and more. Anne is renowned for her mission to build workplaces that blend high performance with humanity.🔗 LinkedIn | WebsiteMentioned ResourcesFacebookMicrosoft ProjectBlue NileeBayTaskRabbitGuru (knowledge management)SendGridGustoPatreonBlockThredUp15 Commitments of Conscious Leadership (framework/book)Stanford Graduate School of BusinessKozmo (Seattle delivery)Important LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiNote: This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside.The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

When was the last time you felt your vision misunderstood, your partnership undervalued, or your operational roadmap tangled? If you’re a COO wrestling with translating big ideas into real impact, this conversation is your lifeline.Sivana Brewer welcomes Stephanie Kauffman, Chief Operating Officer at Melanoma Research Alliance, for an urgent episode that lifts the veil on what actually moves the needle for COOs. From converting financial “legends” into game-changing board allies to crafting story-driven partnerships that triple outcomes, you’ll hear how real-world translation builds trust fast, drives innovation, and prevents career-stalling burnout.Press play now. Don’t risk getting stuck in your leadership bubble. Every minute here arms you with exclusive, proven techniques to connect, influence, and scale before someone else beats you to it.Timestamped Highlights[00:10] – A stunning perspective shift: why “second in command” is really “dual in command” for COOs everywhere[00:02:25] – The myth of melanoma: deadliest form of skin cancer, massive underestimation, and breakthrough facts COOs should know[00:08:21] – Surprising everyday tips for preventing melanoma beyond just sunscreen (plus one you’ve likely never heard)[00:10:39] – How legendary finance leaders shaped Stephanie’s radical “private equity” nonprofit strategy—what every COO can steal[00:18:49] – The $12.7 million secret: bold partnerships that defied board skepticism (and the power of gaming for social impact)[00:27:11] – Data-driven storytelling for buy-in: How Stephanie translates emotional conviction into actionable board wins[00:31:47] – Professional translation: the vital COO role in turning CEO vision into operational clarity for every stakeholder[00:43:15] – The “3 Bs” formula and simplifying the complex: brief, brilliant, be done—your solution to communication chaosAbout the GuestStephanie Kauffman is Chief Operating Officer of the Melanoma Research Alliance, the world’s largest nonprofit funder of melanoma research. Known for high-impact storytelling and cross-industry partnership wins, she previously held SVP roles at Universal Studios and Breast Cancer Research Foundation. Stephanie is recognized for translating visionary ideas into scalable operations, bringing decades of experience across finance, media, and biotech.🔗 LinkedIn | WebsiteMentioned ResourcesBreast Cancer Research FoundationBlizzard Entertainment (Overwatch partnership)Universal Studios (media/partnerships)Leverage Finance Fights Melanoma platformUPF apparel (sun protection clothing)Mafia Wars (gaming partnership)About the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Ever felt like you’re carrying the weight of growth, but struggling to shift your company from band-aids to real, sustainable breakthroughs?Meet Nicki Baty, COO at Freshpet, who’s rewriting the playbook for second-in-command leadership inside a rocketship culture. In this revealing conversation, Nicki Baty opens up to host Sivana Brewer about pioneering a COO role from scratch, installing trust (in teams and at home), and building a business fueled by missionary drive, not mercenaries.Explore how to turn constant change into your secret weapon, earn buy-in when the North Star keeps moving, and design a culture that scales with speed without chaos.You can’t afford to run on autopilot or yesterday's wins. Discover the steps that separate successful COOs from those stuck in a cycle of busyness. Listen now for exclusive insights you can’t afford to miss. The next wave of growth is already here, and this episode holds the edge.Timestamped Highlights[00:00] - The one guarantee for every COO—how to win when change is constant[03:41] - Missionaries vs. mercenaries: Why purpose-driven teams deliver differently[07:40] - Moving a family across continents for growth—what business leaders really learn[12:11] - “Making room in the boat”: Building trust, networks, and resilient teams on the fly[19:12] - Nicki reveals how to plan post-onboarding in a brand new leadership role[23:35] - Finding your “most valuable pet parent” and reshaping the company around them[28:35] - The surprising power of Freshpet's pioneering spirit—and what big companies still get dead wrong[37:13] - The real difference between strategic priorities and tactical noise (and how most teams get stuck)About the GuestNicki Baty is the Chief Operating Officer at Freshpet, a company redefining the pet nutrition industry with its human-grade, refrigerated pet food. Formerly President and General Manager of Hill’s Pet Nutrition US (Colgate-Palmolive), Nicki’s career has spanned the globe—from the UK and Europe to Asia and the Americas. She is recognized for her track record in scaling organizations, her passionate belief in purpose-driven work, and her relentless focus on building trust and sustainable growth in fast-moving environments.🔗 LinkedIn | WebsiteMentioned ResourcesColgate-PalmoliveUnileverHill’s Pet NutritionWalmartTarget10X Is Better Than 2XBryan Johnson (longevity/biohacking)Wellness DaddyAbout the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

What if the biggest threat to your company’s growth is how you show up every day—burned out, distracted, or just going through the motions? Most COOs know the cost of chaos, but few stop to ask what’s driving it inside themselves.Enter Sunil Rajasekar, former President and CTO of Mindbody, who sits down with Cameron Herold for a no-holds-barred conversation about burnout, resilience, and building a global wellness empire with gratitude at its core. From the backstage mechanics of a platform used by millions to the secret link between world-changing tech and personal wellbeing, this episode delivers the eye-opening truths every leader needs.Listen now before your stress becomes your biggest blind spot. Actionable, exclusive, and radically honest. These insights aren’t just a luxury, they’re your lifeline.Timestamped Highlights[00:00] – What nobody tells you about burnout (until it’s too late)[00:03:31] – Why Sunil reversed the script: an origin story you didn’t expect[00:06:15] – The real reasons high-powered execs flame out (and how Sunil rebuilt himself)[00:14:23] – Two CEOs, one mission: Navigating seismic leadership transitions[00:16:50] – Under the hood of Mindbody: Why perfection on the surface means wrestling chaos behind the scenes[00:24:28] – The make-or-break moment for small businesses—and why most lenders get it wrong[00:29:32] – The war for tech talent and how to keep your team’s soul intact[00:33:35] – What COVID proved about wellness, grit, and the “missionary vs. mercenary” divide[00:40:50] – The gratitude ritual that saved Sunil—and could save youAbout the GuestSunil Rajasekar is the former President and Chief Technology Officer at Mindbody, the global platform powering the wellness industry in over 100 countries. With more than two decades leading technology and product transformation at eBay, Intuit, Lithium Technologies, and then Mindbody, Sunil is renowned for scaling businesses that shape industries, without sacrificing the humanity at their core. His mission: Connect the world to wellness, one breakthrough at a time.🔗 LinkedIn | WebsiteMentioned ResourcesMindbody CapitalClassPassVista Equity PartnersBook: “The Mind-Body Connection” by John SarnoBook: “Buddha and the Badass” by Vishen LakhianiMindvalley (Vishen Lakhiani)Tim FerrissUberApple FitnessF45Orangetheory FitnessBooker (acquired by Mindbody)ClearBank (referenced as a similar financial product)Important LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiNote: This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside.The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Are you trapped in operational chaos, fighting burnout, and searching for a formula that actually scales? You’re not alone.This electrifying episode features Guillaume Bouvard, Co-founder, COO and CMO of Extend, as he sits down with Sivana Brewer to reveal the real-life victories and invisible battles behind explosive fintech growth. From his unusual rise at American Express to building a team of true experts (not just generalists), Guillaume exposes the proven rituals, painful lessons, and cultural shifts that unstick founders and COOs worldwide.If you’ve ever wrestled with hiring mistakes, boardroom pressure, or the fear of letting go, this conversation is your playbook for escaping overwhelm right now. Tune in for exclusive strategies you won’t hear from the usual talking heads—and avoid the pain of staying stuck another quarter. Listen now, because your breakthrough can’t wait and these field-tested insights are only found here.Timestamped Highlights[00:00] – The daring anti-micromanagement view that reshaped a whole company’s culture[00:07:08] – Why Guillaume became COO and what most founders never tell you about picking partners[00:09:12] – How a “no two days alike” mindset powers world-class operations without chaos[00:12:27] – The little-known boardroom rituals that drive results, build trust, and end nasty surprises[00:19:44] – Guillaume’s radical philosophy for staying engaged, focused, and unshakable against daily setbacks[00:21:01] – The breakthrough hiring lesson that can rescue any leader from burnout (before it’s too late)[00:28:14] – Steal-this-process: Monday all-hands, relentless transparency, and celebrating the hidden heroes[00:34:29] – Real-life wins: How a single empowered team member triggered a market wave using curiosityAbout the GuestGuillaume Bouvard is the Co-founder, Chief Operating Officer, and Chief Marketing Officer of Extend, a venture-backed digital credit card platform revolutionizing spend management for banks and businesses. With more than two decades of leadership across American Express and international fintech, Guillaume blends corporate discipline with disruptive startup agility. His obsession with hiring world-class talent, building intentional culture, and empowering true ownership makes him a sought-after voice for COOs ready to scale with clarity and conviction.🔗 LinkedIn | WebsiteMentioned ResourcesAmerican ExpressBank of Montreal (BMO)HSBCPayPalUSCIS (U.S. immigration agency)SlackOKRs (Objectives and Key Results Framework)About the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

What if your next breakthrough isn’t more hustle, but ruthless focus on what actually matters?Scott Levy, Fractional COO of ResultMaps, joins Sivana Brewer for a candid, zero-fluff conversation on why most CEOs and COOs are drowning in distraction and what separates “second in command” leaders who skyrocket growth from those stuck grinding. They pull apart why ambitious teams spiral into task overload, the critical metrics every department truly needs, and the battle-tested rituals that free up your brain for high-stakes decisions.Ready to step off the treadmill of constant fires, endless meetings, and “yet another platform” promises? This episode exposes the cost of delay and throws you a direct path out, real systems, real clarity, real results. If you wait, you risk another year of burnout and missed breakthroughs. Press play now for inside strategies unavailable anywhere else.Timestamped Highlights[00:54] – Why “good” content became too dangerous for Speaker A to binge (and what that reveals about focus)[02:09] – The real operations heartbreaks hidden behind entrepreneurial success stories[07:09] – Why small teams will devour giants in the AI revolution (the Special Forces lesson nobody teaches MBAs)[10:34] – The shockingly simple hack for bypassing bloated CRMs and running your pipeline on autopilot[12:02] – How to extract a Vivid Vision in 30 minutes—no trust falls required[16:13] – “Eff your feelings, follow the plan?” Dissecting the truth (and limits) of systemizing emotional chaos[26:52] – The fatal flaw of cascading goals—and what truly separates winners from burned-out operators[44:36] – The raw moment CEOs finally break—and why some refuse to suffer the same mistakes twiceAbout the GuestScott Levy is the Founder and CEO of ResultMaps, a cutting-edge SaaS platform designed to help founders and leadership teams obliterate operational friction, scale clarity, and get real results. With a background spanning management consulting, software, and building systems for high-growth companies, Scott’s passion is turning entrepreneurial chaos into decisive execution. He’s especially known for integrating technology and coaching with powerful simplicity.🔗 LinkedIn | WebsiteMentioned ResourcesLeila HormoziGrok (AI tool)FigmaCole Gordon/Closers.iohttps://www.linkedin.com/in/cole-gordon/EOS (Entrepreneurial Operating System)OKRs (Objectives and Key Results)GrowRevJohn Humphrey, Connect Points frameworkTony RobbinsAppleTesla (re: Grok in-car integration)About the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Are you overwhelmed by nonstop chaos, endless stakeholder demands, or the fear you’ll break while scaling up? This episode delivers urgent answers for every COO, integrator, and senior ops leader pushing to get their head above water.Cameron Herold sits down with Kelly Knight, President and Integrator of EOS Worldwide, for a rare, candid look at the systems and mindset that power explosive growth and keep organizations aligned when everything feels impossible. Kelly lifts the curtain on EOS’s real role in revolutionizing the “second in command” function, gives you her hard-won playbook for winning over visionaries, and exposes how elite integrators preserve culture, even through private equity takeovers and seismic business model shifts.Stop guessing and start winning. Listen now to avoid burnout, grab proven EOS secrets, and finally align your team before something breaks. These insights are exclusive, actionable, and you won’t hear them anywhere else.Timestamped Highlights[00:00] – Chaos or clarity? How EOS aligns human energy when everything’s changing[00:02:41] – Why most “second in command” titles are missing the mark (and where EOS fits in)[00:03:27] – The system for managing human energy that built a raving fandom[00:07:14] – Inside the “VI Duo”—the secret sauce that powers badass leadership teams[00:10:11] – One killer meeting rhythm that keeps visionaries and integrators in lockstep[00:13:02] – From outsider to integrator: Kelly’s surprising first 90 days and the mistake even top COOs make[00:17:03] – Private equity chaos? How Kelly realigned 27 stakeholder groups and survived[00:27:01] – Navigating massive change: Candid truths about communication, relationships, and earning trust[00:29:44] – Why EOS failed at software and the power of doubling down on your “hedgehog”About the GuestKelly Knight is the President & Integrator of EOS Worldwide, the pioneering force behind Entrepreneurial Operating System®. Known for her expertise in scaling operations, leadership development, and stakeholder alignment, Kelly has guided EOS through private equity acquisition and global expansion. She regularly mentors visionary-operator duos around the world, helping them navigate change and build lasting company culture.🔗 LinkedIn | WebsiteMentioned ResourcesTraction (book)Rocket Fuel (book)Kolbe (assessment)Strategic Coach (Dan Sullivan)1-800-GOT-JUNKninety.io (software partner)Verne HarnishFirefly Group (private equity)Basecamp (training resource)StrengthsFindersMyers-BriggsChatGPTGrokImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

What if you could transform a team of rookies into high-performing, loyal leaders and stay sane in the process?This episode delivers an unfiltered look inside the mind of Richard Comitz, Chief Operating Officer of American Corporate Partners, a West Point PhD and retired Army Lieutenant Colonel now leading one of America’s most mission-driven nonprofits. He sits down with Narrator to unpack the proven discipline, radical transparency, and mentorship strategies he honed in combat and now deploys to scale an 80-person organization serving over 5,000 mentorships nationwide.Want to dodge burnout, ignite next-gen talent, and finally get your CEO partnerships working for—not against—you? Listen now. Skip it, and you risk getting buried by the next Ops crisis. This is an urgent, inside-access episode you won’t find anywhere else.Timestamped Highlights[00:00] – The leadership power move that made junior staff instantly trust Richard Comitz[00:04:12] – Why a PhD, combat zones, and organic chemistry are COO superpowers (and how higher ed nearly cost him)[00:08:48] – How to “inherit” a role from a founder without clashing or caving[00:13:05] – The secret architecture behind training 60+ brand-new hires (and spotting future all-stars fast)[00:15:53] – Shocking truths of what actually works to fight young-employee burnout and what never does[00:19:30] – Hidden mentorship hacks that win powerful partners in Fortune 500s[00:23:16] – Does military “figure it out” energy work with Gen Z? The raw reality from the field[00:37:26] – Navigating founder-CEO rigidity and pitching bold new ideas (without ending up fired)About the GuestRichard Comitz is the Chief Operating Officer of American Corporate Partners (ACP), a powerhouse nonprofit connecting U.S. veterans and military spouses with Fortune 500 mentors for next-level careers. A retired Army Lieutenant Colonel, West Point organic chemistry instructor, and experienced higher education COO, Comitz is celebrated for turning disciplined military leadership into explosive organizational growth in both the public and nonprofit sectors.🔗 LinkedIn | WebsiteMentioned ResourcesPeter Attia (podcast, health and nutrition)Andrew Huberman (Huberman Lab, neuroscience podcast)Jocko Podcast by Jocko Willink (Extreme Ownership, Navy SEAL leadership lessons)Joe Rogan Experience (podcast)Extreme Ownership by Jocko Willink (book)West Point (U.S. Military Academy)About the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

What if the difference between scaling up and burning out comes down to just one overlooked decision you make today?In this exclusive Second in Command episode, Cameron Herold sits down with Jon McNeill, former President of Tesla and COO of Lyft, and current CEO and Co-Founder of DVx Ventures, for a bold, eye-opening deep dive into the raw realities of being second in command at companies that redefine entire industries.You’ll hear battle-tested lessons on navigating visionary founders, eliminating organizational bloat, and building operating systems that drive exponential growth, plus what most leaders get dead wrong about innovation, hiring, and execution at scale.If you crave real-world playbooks and not more recycled platitudes, hit play now. Miss this conversation and risk falling into the same chaos that sinks even the greatest companies. Listen today to steal field-proven COO frameworks you won’t hear anywhere else before your competition does.Timestamped Highlights[00:03:16] – The $108 million mistake: why Jon McNeill turned down Uber and Tesla before they became giants[00:07:22] – From Bain to boardrooms: how Cameron Herold went from $1.8B to $20B in 30 months[00:14:49] – What it really feels like to drop into Tesla’s leadership team—no roadmap, only chaos[00:17:04] – The pivotal moment Cameron Herold broke the rules at Tesla and why Elon Musk said “You’ll fit right in”[00:21:09] – The “Big Thing” meeting—the deceptively simple method Cameron Herold stole from Facebook’s top minds[00:26:43] – How to push back (and win) with the world’s most demanding CEO[00:36:11] – The ruthless self-topgrading system that kept Tesla lean—could you survive it?[00:47:11] – Tesla’s “Algorithm” revealed: the counterintuitive systems any leader can stealAbout the GuestJon McNeill is the former President of Tesla and COO of Lyft, a renowned serial entrepreneur, and current CEO and Co-founder of DVx Ventures. Recognized for multiplying company valuations and pioneering operational mastery at the world’s most innovative companies, Jon now empowers founders and operators to scale with speed and discipline. His latest book, The Algorithm, reveals the operating system behind Tesla’s success and is quickly becoming a must-read for growth-focused leaders.🔗 LinkedIn | WebsiteMentioned ResourcesTeslaLyftBain & CompanyBain CapitalAndreessen Horowitz1-800-GOT-JUNKFacebook (Mark Zuckerberg, Sheryl Sandberg)Uber (Travis Kalanick, Garrett Camp)Tim FerrissSolarCity (Pete Reeve, Lyndon Rive)College Pro PaintersSpaceXSalesforceYPOQueen’s UniversityHard Thing About Hard Things (Ben Horowitz – book)Good to Great (Jim Collins – book)Insanely Simple (Ken Segall – book)Important LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Ever wonder why some COOs scale businesses to legendary heights while others get swallowed by chaos and politics? If you’re craving clarity, confidence, and uncommon edge in your second-in-command role, this Fan Favorite episode is your wake-up call. Cameron Herold sits down with Matt MacInnis, COO of Rippling and co-founder of Inkling, for a raw, actionable conversation about the real challenges behind hyper-growth, hiring, trust, and culture. They dig into what makes the COO role so “special,” how to build a game-changing flywheel, and why patience, precision, and authenticity are the ultimate power moves.The pain of “going it alone” is real. Tune in to learn how to avoid disaster, dodge politics, and harness proven tactics you won’t find in any business book. Don’t wait until burnout bites. Listen now for fiercely exclusive COO insights, bold truths, and systems that will let you scale smarter, not harder.Timestamped Highlights[00:02:22] – The hidden pain in HR, IT, and how Rippling breaks the “original sin” of bad data[00:05:55] – Why Matt almost walked away—then got schooled by Parker’s contrarian “rocket ship” logic[00:08:30] – The untold power of preexisting trust between CEO and COO—and what happens if you hire without it[00:12:49] – Topgrading secrets: Why most executive hiring fails and how to get it right (even when everyone says they’re an “A player”)[00:15:44] – Copilot dynamics: How Matt and Parker run the company with surprisingly little contact (and why it works)[00:19:18] – Should you debate the CEO in front of the team? The cathartic, risky art of public disagreement[00:23:13] – Inside Rippling’s flywheel advantage—what Salesforce, Facebook, and Brex did differently and why you can too[00:31:04] – Killing bureaucracy and politics: The simple rule for hiring and process that most leaders ignore[00:39:29] – The brutal, proven formula for layoffs: What Sequoia teaches (and how to survive the “survivor’s guilt”)About the GuestMatt MacInnis is the Chief Operating Officer of Rippling, a revolutionary all-in-one HR and IT platform transforming how businesses scale and manage people. Matt was also the co-founder and CEO of Inkling, a mobile learning platform that raised over $100M before its acquisition. With deep roots at Apple and a Harvard engineering degree, Matt blends big-company brilliance with entrepreneurial firepower. He’s known for breaking boring business norms and igniting hyper-growth, all while refusing to tolerate politics, inefficiency, or shallow executive hiring.🔗 LinkedIn | WebsiteMentioned ResourcesInklingAppleHarvardParker Conrad (Rippling CEO)ADPGustoDropboxSlackWorkdayOktaBrexMarketoSalesforceSequoiaKleiner PerkinsBrad Smart (Topgrading) | Topgrading (book)Who (book) | Geoff Smart (Who)Elad Gil | The High Growth HandbookImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiNote: This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside.The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Feeling the pressure to scale but terrified of losing your best people, or watching team morale dissolve as your business grows?This episode, guest host Sivana Brewer gets real with Isaac Tobelen, current CMO at Springs Rejuvenation and seasoned COO, on the inside challenges of recruiting, retaining, and motivating talent in rapid-growth settings. Isaac shares proven systems for hiring culture-aligned operators, the brutal mistakes that cost him top performers, and how “Innovation Day” became a surprising game-changer for agency culture.If you want actionable tactics to build a resilient team and avoid silent exits, listen now, not later. Your next big hire, retention strategy, or culture upgrade may hinge on these lessons. Tune in for exclusive, hard-won insights that most COOs only learn the hard way.Timestamped Highlights[00:00] – The “quiet risk” that nearly cratered Isaac’s agency and why losing one key player can trigger a domino effect[03:08] – Rewiring direct response marketing for an unexpected industry and scaling it to $1.2M/month[08:59] – Why competitors keep stealing Isaac’s ads, but can’t touch his team’s execution[11:08] – The secret overlap of visionary CEO and practical COO—why it worked for Isaac and Ashton[13:49] – How teaching people “how to think” crushed micromanagement and burnout[15:02] – The counterintuitive hiring process that filters for real values (not just resume skills)[24:29] – Unconventional interview tactics, homework, and the non-negotiables that reveal true fit[32:00] – “Innovation Day” revealed – How letting teams fail forward built trust and inspired breakthrough creativity[38:11] – Isaac’s 2 biggest mistakes: concentrated risk and a disastrous acquisition—what he’d do differently[52:44] – Is AI really changing everything? Isaac’s blunt take on what’s hype, what actually matters, and why talent must upskill nowAbout the GuestIsaac Tobelen is the Chief Marketing Officer at Springs Rejuvenation, a leader in stem cell and exosome therapy. Previously, he was COO at Hemon Media, where he scaled the agency to $500K/month in 18 months, managed $36M+ ad budgets, and built high-performing teams from scratch. Isaac is known for his systems thinking, rapid operational scale, and real-world people development.🔗 LinkedIn | WebsiteMentioned ResourcesFrank Kern (Mass Control)ClickUpAsanaJim Collins (“flywheel” concept)EOS – Entrepreneurial Operating SystemAbout the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Ever wondered how legendary operations leaders onboard 800 seasonal hires for world-class performance in just 30 minutes? What if your biggest edge wasn’t tech, but radical clarity, proven systems, and the courage to democratize what most companies hide?In this revealing conversation, guest host Sivana Brewer sits down with Tom Root, Managing Partner at Zingerman’s Mail Order and a driving force behind its remarkable open-book management culture. Tom isn’t just running a $24M operation; he’s helping to architect the Zingerman’s way, a playbook that turns consensus, culture, and scientific thinking into a market advantage.Dive in to discover how Tom’s team hires 800 people for the holidays, keeps SOPs thrillingly relevant, leverages just-in-time knowledge systems, and makes “lean” truly work. If you crave real answers on scaling without chaos or losing culture, THIS episode is your exclusive playbook to operational victory. Listen now to avoid another year of stalled growth, outdated systems, and disconnected teams.Timestamped Highlights[00:00] – Why “democratization” is a double-edged sword for accountability[03:07] – Zingerman’s wild origin: Russian anarchists, consensus, no classic CEO—and their bold growth vision[06:37] – Why illustrated food (not photos) is marketing magic…and why it works[13:27] – The single ops lever for onboarding 800 people in 30 minutes (no, it’s not superstar managers)[17:28] – Secrets behind just-in-time knowledge, digital twins, and how training is dead[23:15] – “Tim’s Law”: What happens when only one person “knows everything” and how to fix it[28:41] – Radical SOP audits, the core mistake most leaders make (and how Tom solved it)[31:39] – How open-book management paid off $300K debt and kept Zingerman’s profitable every year since[42:09] – Scientific thinking vs. the “tools” trap, and why organizations resist outsidAbout the GuestTom Root is Managing Partner at Zingerman’s Mail Order, part of the legendary Zingerman’s Community of Businesses in Michigan. He’s recognized for championing open book management, building empowered teams, and pioneering proven operational systems that help Zingerman’s scale their beloved brand while keeping culture alive. Tom’s unique perspective joins hands-on leadership with a background in tech, manufacturing, and continuous improvement.🔗 LinkedIn | WebsiteMentioned ResourcesZingerman’s Community of BusinessesOpen Book ManagementLean Manufacturing / Toyota KataGoogle Sites (for internal wikis)The Great Game of Business by Jack StackZingerman’s BakehouseUniversity of Michigan (operations partnerships)About the Co-HostSivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.🔗 Connect with Sivana on LinkedInImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via DelphiThe Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.