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

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

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Welcome to the “Second in Command” Podcast hosted by Cameron Herold, brought to you by the COO Alliance, where top-level COOs share their insights, tactics, and strategies that made them the Chief Behind the Chief. Cameron Herold founded the COO Alliance with one simple goal in mind: to provide COOs with the same professional development and growth opportunities CEOs have enjoyed for many years. COO Alliance is the world's leading network for the Second in Command. Cameron Herold is a top business consultant, best-selling author, and speaker. He’s the mastermind behind hundreds of companies’ exponential growth and he’s touched thousands of businesses indirectly through his work.Copyright 2026 Second in Command with Cameron Herold Développement commercial et entrepreneuriat Entrepreneurship Gestion et leadership Économie
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  • Ep. 573 - WEBTOON Global CFO and COO David Lee - Why Most Leaders Play Small… and How to Escape
    Apr 23 2026
    What if the biggest thing holding your company back… is how you’re thinking about what’s possible?In this episode, David J. Lee, Global CFO and COO of WEBTOON, breaks down a radically different way to approach growth, leadership, and innovation. From scaling a global storytelling platform with 155 million users to partnering with visionary founders, David shares how elite operators think beyond “high probability outcomes” and instead build toward what must be true to achieve breakthrough success.This conversation dives into the realities of being a COO at scale, navigating public company pressure, leading global teams, and building trust with mission-driven founders.If you’re tired of incremental thinking and want to unlock bold, category-defining growth, don’t wait. The longer you operate within “safe” assumptions, the more opportunity you lose. Hit play now for a rare, high-level perspective most leaders never access.Timestamped Highlights[00:00] – The mental trap that keeps leaders stuck in “safe” growth instead of breakthroughs[02:32] – Inside WEBTOON: 155M users, 24M creators, and a global storytelling revolution[05:47] – Why the best operators don’t specialize, and the real cost of being a generalist[08:49] – The one question great leaders obsess over that most companies ignore[11:28] – The brutal reality of going public, and why it forces true discipline[15:41] – What separates high-integrity founders from the rest, and how it shows up daily[19:01] – When a COO should stay… and when it’s time to walk away[23:17] – How elite leaders stay calm in chaos, even in high-stakes environments[26:23] – The hidden danger of “oversteering” and why great leaders step back[33:14] – The “what must be true” framework used by NASA and top innovatorsAbout the GuestDavid J. Lee is the Global CFO and COO of WEBTOON, a global storytelling platform connecting millions of creators with over 150 million users worldwide. He has led major transformations across companies like Zynga, Impossible Foods, and Best Buy, bringing a unique blend of strategy, operations, and innovation to high-growth environments. Known for partnering with visionary founders, David specializes in scaling companies that are redefining entire industries.🔗 LinkedIn | WebsiteMentioned ResourcesImpossible FoodsZyngaBest BuyRhode Island School of Design (RISD)NASDAQAbout 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/Disclaimer: This episode was recorded on December 8, 2025. At the time of recording, David J. Lee had not yet assumed his current role. He is now the President of Wattpad and also serves as the Global Chief Financial Officer of WEBTOON Entertainment. Please note that any references in this conversation may not reflect his most up-to-date titles or responsibilities.
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    42 min
  • Ep. 572 - FAN FAVORITE | Sean Kim (HighLevel CPO, Former Kajabi President, Ex-Amazon, TikTok): Conquer Imposter Syndrome and Lead Powerfully
    Apr 21 2026
    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.
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    37 min
  • Ep. 571 - Grindr Former COO Rick Marini - How to Spot A-Players and Deliver Big Results Fast
    Apr 16 2026
    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/
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    45 min
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