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

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• Ep. 584 - FAN FAVORITE | Former KENNEDY24 Presidential Campaign Director Amaryllis Kennedy – How to Build an Unstoppable Political Campaign Machine 02.06.2026 1godz 2min

  What do you risk when you run a mission-driven campaign that breaks every rule in politics? Amaryllis Kennedy isn’t just directing the KENNEDY24 presidential campaign. She’s rewriting the playbook on grassroots leadership, digital disruption, and brutal operational honesty.In this Fan Favorite unfiltered episode, Cameron Herold dives deep with Amaryllis on the real strategies behind building a nimble, values-first organization in the most polarized landscape imaginable. She reveals the raw tension of building trust, keeping chaos at bay, and rescuing authenticity from a world addicted to power and performance. Hard-won lessons from Silicon Valley and the CIA collide with everyday realities of parenting, digital activism, and fighting the system from the inside.If you miss this conversation, you miss the forbidden playbook on what leadership really looks like when the stakes are generational. Listen now for a front-row seat on strategy you won’t get anywhere else and discover why the real power lies in what you’re willing to disrupt.Timestamped Highlights00:44 – The counterintuitive campaign strategy that energizes a disillusioned public05:17 – Why young people are secretly shaping America’s future08:05 – How breaking political storytelling rules actually breaks through13:04 – The brutal inside story behind government overreach19:47 – A behind-the-scenes look into a campaign where careers are truly on the line24:00 – The ballot access chaos that forces real innovation30:31 – Why authenticity beats perfection in a runaway grassroots movement35:32 – Democratizing campaign fundraising with bold gamified tactics47:44 – The sacred job of protecting your leader so they can really listen59:35 – The surprising benefit of Sabbath-style strategy in hypergrowthAbout the GuestAmaryllis Fox Kennedy is a former CIA intelligence officer, author, and advocate focused on diplomacy, conflict resolution, and public policy. She is the bestselling author of Life Undercover: Coming of Age in the CIA and host of Netflix’s The Business of Drugs. She also served as a senior advisor and campaign surrogate during Robert F. Kennedy Jr.’s 2024 presidential campaign. She currently serves as Deputy Director of National Intelligence for Policy and Capabilities.🔗 WebsiteMentioned ResourcesKENNEDY24 campaignNetflix – The Business of DrugsApple – TV series based on Amaryllis's memoirBobby Kennedy Jr.Conde NastHearstGenius NetworkBurning ManTwitter (as previous tech experience)Georgetown UniversityOxford UniversityBrown University (used as a reference for war statistics)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.
• Ep. 583 - NSBE CFO & COO Stanton Hill - How to Build Unstoppable COO Teams That Win 28.05.2026 46min

  What does it really take to sit in the second seat and do it with drive, grace, and guts? In this episode, Lindsay uncovers the journey and mindset of Stanton Hill, the Chief Financial and Operating Officer for the National Society of Black Engineers. From his unexpected path into leadership to the high-stakes pivots required during a crisis, Stanton Hill reveals the nuts and bolts (and the emotional work) of steering a student-governed organization with 25,000+ members.If you’re wrestling with hybrid teams, retention headaches, or scaling real culture, this is your masterclass. Avoid missing real-world tactics on delegation, resilience, and helping people thrive even when the world flips upside down. Listen now for the brutal, refreshing clarity on what it takes to lead from the number two seat while building a legacy that outlasts your title.Timestamped Highlights00:40 – The real reason student governance keeps NSBE thriving02:22 – The moment a father invests for life in his son’s future06:04 – How a COO earns trust and evolves during big leadership shifts10:06 – Brutal revenue risks when in-person events collapse overnight13:02 – The hidden reality behind hybrid events few executives know16:12 – Career fair hacks that build total confidence in seconds17:20 – The overlooked muscle every COO needs: leading with empathy29:07 – The ruthless approach to blocking out overwhelm, not just emails40:12 – How personal adversity can forge leaders who never flinchAbout the GuestStanton Hill brings two decades of experience in financial strategy and nonprofit operations. Prior to joining NSBE, he held several roles at the United Negro College Fund (UNCF), where he managed multimillion-dollar operating budgets, streamlined financial processes, and led grant management initiatives totaling over $30 million. He began his career with a focus on business analytics and process optimization and has since advanced through NSBE's leadership ranks: from Director of Finance and Accounting to Chief Financial Officer, and now Chief Financial & Operating Officer. Stanton Hill earned his Bachelor of Arts in Business Administration from Morehouse College and a Master of Business Administration with a concentration in Innovation, Entrepreneurship, and High Technology from Northeastern University. He resides in Georgia with his wife Adrienne and their sons Davis and Carter. 🔗 LinkedIn | WebsiteMentioned ResourcesUnited Negro College Fund (UNCF)Six SigmaProject Management Professional (PMP)About the Co-HostLindsay Smith is an experience-driven growth strategist and former Chief Strategy Officer who 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.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: http://www.redirectcoo.com/
• Ep. 582 - FAN FAVORITE | Somewhere COO Benjamin Surman – How Top COOs Slash Headcount and Boost Profits 26.05.2026 38min

  What if cutting half your team could be the secret to explosive growth?In this Fan Favorite episode, Cameron Herold sits down with Benjamin Surman, COO of Somewhere (formerly Support Shepherd), a company that rocketed from $1M to $25M and is still hungry for more. The conversation tackles the real-world, often-unspoken operational questions: When do you fire instead of hire? Where’s the hidden margin in automation? Why are so many leaders clinging to headcount when systems could do the job faster, cheaper, and with less chaos?If you’re addicted to the idea that bigger is always better, this episode will shake your assumptions. Miss it and risk drowning in legacy thinking while your competitors eat your lunch. Listen now for the strategic edge you won’t hear anywhere else.Timestamped Highlights00:48 – The real reason behind a bold global rebrand02:29 – How one contractor quietly took the reins as COO08:54 – Why bootstrapping (not VC money) set the right culture11:00 – The micro-influencer lever that brings 4,000 referral partners13:25 – What no one tells you about hiring in Latin America17:41 – The $3M decision: Slashing 120 employees with zero regrets20:13 – Behind the curtain of an automated sales pipeline25:37 – The COO playbook for uncovering invisible inefficienciesAbout the GuestBenjamin Surman is the Chief Operating Officer of Somewhere, a hyper-growth headhunting agency revolutionizing global talent acquisition. With a relentless focus on automation and operational excellence, Benjamin Surman has scaled the business from $1M to over $25M in just three years.🔗 LinkedIn | WebsiteMentioned ResourcesMy First Million PodcastSean Puri, Sam Parr, Nick HuberHubSpotRecruit CRMMichael Gerber – The E Myth RevisitedImportant 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.
• Ep. 581 - CoinMe COO Sung Choi - Life After Acquisition: Surprising Wins and Brutal Costs 21.05.2026 41min

  What happens when a regulated fintech meets the wild swings of crypto and then gets acquired by a Web3 giant?In this no-fluff conversation, Cameron Herold sits face-to-face with Sung Choi, COO of CoinMe, just months after their high-stakes Polygon Labs acquisition. They get blunt about what it really takes to survive in crypto, how to lead through M&A chaos without losing your best people, and why AI is rapidly rewriting the rules of operational excellence.If you want to hear war stories and hard-earned lessons from the frontlines of scaling a volatile, regulated business, this is your episode. Don’t risk missing the sharpest insights on leadership, remote culture, and how to stay relevant through uncertainty. Listen now for playbook-level takeaways you won’t get anywhere else.This episode is brought to you by our Silver Sponsor, Next Level Growth.They help COOs and leadership teams build Elite Organizations through a proven, customizable framework built around the Five Obsessions of Elite Organizations.If you and your leadership team are ready to operate at the next level, take the Elite Organizations Assessment and receive a free 20-page customized report based on your answers, plus a complimentary one-hour coaching session with a Next Level Growth Partner and Business Guide to begin implementing tools that will help you build an even more elite business.Complete the assessment here to get started - nextlevelgrowth.com/cooassessmentTimestamped Highlights00:06 – The brutal reality of CoinMe’s early hardware dreams11:10 – Why powering partners crushed owning infrastructure13:04 – “M&A is like polyamorous dating” and what nobody tells you17:14 – The tension of disclosure and keeping employees sane22:25 – A surprising pivot: from bitcoin hype to stablecoin utility26:29 – The regrets and rewards of abandoning office life30:26 – How “work from anywhere” delivers hidden productivity34:01 – Why AI is now their secret operating system44:23 – The one leadership skill every modern COO must masterAbout the GuestSung Choi is the Chief Operating Officer at CoinMe, a leading regulated platform for stablecoin and crypto payments. With full-stack experience in scaling teams and driving innovation, he steered CoinMe through its pivotal acquisition by Polygon Labs. Sung Choi is recognized for blending real-world grit with bleeding-edge tech in fintech.🔗 LinkedIn | WebsiteMentioned ResourcesPolygon LabsCoinstarPantera CapitalDigital Currency Group (DCG)Gemini (AI tool)Claude (AI tool)ChatGPTiTex (formerly ubarter.com)Goldman SachsOKRs frameworkImportant 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.This episode is brought to you by our Silver Sponsor, Next Level Growth.They help COOs and leadership teams build Elite Organizations through a proven, customizable framework built around the Five Obsessions of Elite Organizations.If you and your leadership team are ready to operate at the next level, take the Elite Organizations Assessment and receive a free 20-page customized report based on your answers, plus a complimentary one-hour coaching session with a Next Level Growth Partner and Business Guide to begin implementing tools that will help you build an even more elite business.Complete the assessment here to get started - nextlevelgrowth.com/cooassessment
• Ep. 580 - Rapid SOS President & COO José Mejia - Why Every COO Needs a Merlin-Style Leadership Edge 19.05.2026 56min

  What if the best leaders are the least visible? In this episode, José Mejia pulls back the curtain on how a Venezuelan teen with just $120 became a transformational COO, unpacking what it really means to be the “Merlin” behind the CEO. This intimate conversation unlocks how true leaders create common ground, give permission to execute, and wield vulnerability as a superpower, especially in high-stakes, purpose-driven companies like Rapid SOS.If you think AI will automate your edge, think again. José Mejia shows why the human element, experiences, handwritten notes, and emotional role modeling, drive outcomes tech never will. Miss this episode, and you keep searching for culture and leadership hacks, while the real magic quietly passes you by. Push play now for insights you won’t find anywhere else.This episode is sponsored by our Silver Sponsor, STS Capital Partners: Your expert guides on the journey to an Extraordinary Exit™. To learn more about STS Capital Partners and how they achieve maximum value by Selling to Strategics™, complete the inquiry form here: https://stscapital.com/coo-alliance/Timestamped Highlights00:33 – The unlikely airport arrival that rewired Jose’s confidence for life06:24 – The “self-directed team” principle that built a 40-year inner circle09:16 – Why leaders must channel Merlin, not the King, to win with teams11:18 – The brutal difference purpose makes when lives are on the line13:23 – What true CEO-COO alignment REALLY looks like behind closed doors16:44 – Underground, Battleground, Common Ground: The language that kills or creates culture20:12 – How AI quietly transforms operator decisions in real emergencies31:05 – The unspoken burden of leading a company where mistakes can cost livesAbout the GuestJosé Mejia is the President and COO of Rapid SOS, leading a team of 500+ to save lives at scale. With a career spanning IBM, Lucent, and high-growth startups, Jose has built self-directed teams and organizational cultures admired worldwide. His “Merlin” approach to leadership is redefining how rapid-growth companies scale with heart.🔗 LinkedIn | WebsiteMentioned ResourcesIBMDuke UniversityLucent and Bell LabsAndy Grove (former CEO of Intel; High Output Management book)Soul on Fire (book and movie)Magic Cabaret, ChicagoSlackGoogle DocsAbout the Co-HostLindsay Smith is an experience-driven growth strategist and former Chief Strategy Officer who 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.This episode is sponsored by our Silver Sponsor, STS Capital Partners: Your expert guides on the journey to an Extraordinary Exit™. To learn more about STS Capital Partners and how they achieve maximum value by Selling to Strategics™, complete the inquiry form here: https://stscapital.com/coo-alliance/
• Ep. 579 - Critical Control COO & Co-Founder Claudine Ripert - Warning: The Critical Mistake Leaders Make in Crisis 14.05.2026 38min

  Ever felt that urge to take total control, only to realize it throttled your team’s growth and your own sanity?Claudine Ripert, COO and co-founder of Critical Control, and COO Alliance member, joins this fierce, truth-telling conversation about leading a fast-scaling restoration business through chaos, disaster, and family dynamics.You’ll hear what it really takes to balance everyday emergencies with unplanned catastrophe, all while steering a company with your own son as CEO. Expect real talk on delegation, brutal lessons learned, what women face in construction, and the psychological traps that kill momentum.Miss this episode, and you risk driving your business into burnout, not breakthrough. Listen now for raw, exclusive wisdom you won’t find in glossy leadership books—only from those who have lived it and bled for it.Timestamped Highlights06:12 – The real chaos of disaster recovery nobody tells you10:05 – Why chasing growth can sabotage your core business overnight14:05 – The unexpected curse of working with family17:00 – The radical communication exercise that finally changed everything22:29 – Brutal truths about enabling and hiring for potential27:15 – The moment Claudine Ripert stopped being a control freak30:06 – The shift from “majoring in the minors” to critical thinking41:46 – Why the right broker referral beats insurance programs every timeAbout the GuestClaudine Ripert is the COO and cofounder of Critical Control Restoration, and COO Alliance member, leading regional disaster recovery operations in California with a national footprint during major catastrophes. Known for scaling her family business through intense market disruption and emotional upheaval, she blends operational rigor with human vulnerability that few in her industry will discuss.🔗 LinkedIn | WebsiteMentioned ResourcesWho by Geoff SmartCAFE (Canadian Association of Family Enterprise)Maslow’s Hierarchy of NeedsCollege Pro Painters1-800-GOT-JUNKGerber Auto Collision/Boyd Auto BodyImportant 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 byGenius 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/
• Ep. 578 - Savannah Bananas President Jared Orton – How Fun Became the Ultimate Competitive Advantage 12.05.2026 50min

  What happens when you set out to break every rule in one of America’s most traditional sports, and people flock to watch?In this Fan Favorite episode, Jared Orton, President of the Savannah Bananas, unpacks how a no-name baseball team triggered a movement by making fun non-negotiable and burning down industry norms. Discover how relentless experiments, cultural friction, player resistance, and pandemic chaos forced Jared Orton and his team to make brutal business choices, all while scaling from selling a few tickets to filling stadiums across America.Miss this episode, and you risk clinging to safe growth strategies while your competitors reinvent, electrify their culture, and claim your customers. Listen now. Get the raw, strategic truth behind explosive growth and team alignment that most leaders never hear about.Timestamped Highlights00:00 – Why telling fans “You can’t buy a ticket” made them desperate to get in03:34 – The culture playbook that turned baseball on its head07:59 – The brutal truth: fun was their only real competitive edge12:03 – The $15 all-you-can-eat gamble that shocked their market15:39 – How they engineer relentless fun without losing operational discipline20:44 – Why letting the wrong players walk is a proven culture win25:00 – The pandemic forced a do-or-die vision shift overnight34:00 – Their biggest tactical mistake and how it nearly cost everythingAbout the GuestJared Orton is the President of the Savannah Bananas, an electrifying baseball brand known for redefining the fan experience and selling out stadiums nationwide. With a proven track record in entertainment-driven growth, Jared Orton has transformed the Savannah Bananas from a struggling local team into a national phenomenon.🔗 LinkedIn | WebsiteMentioned ResourcesVision Driven Leader by Michael HyattMastermind Talks (MMT)Jim Collins – Good to Great, the “Hedgehog Concept”Stephen Covey – 7 Habits of Highly Effective PeopleBanana Ball rulesWalt Disney WorldPixar (Toy Story creative strategy)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.
• Ep. 577 - International Council for Small Business (ICSB) COO Skye Blanks - How To Turn Any Vision Into a Successful Reality 07.05.2026 44min

  What happens when you’re the glue holding a global mission together, but the glue starts to crack?In this electric conversation, Sivana Brewer digs into the trenches with Skye Blanks, COO of the International Council for Small Business, an entrepreneur, and a relentless global operator. They expose the raw truth behind cross-border team dynamics, the weight of relentless travel, and the personal toll of constant responsibility. This episode tears open the unfiltered reality of getting things done, teaching accountability, and building operational systems when the stakes and time zones are always changing.Listen now or risk missing the proven tactics and hard-won lessons that separate thriving leaders from burned-out managers. If you’re ready to weaponize transparency, claim your seat at the table, and cut through nonprofit noise, this conversation is for you.Timestamped Highlights00:31 – The “born operator” mindset that shaped a global COO02:36 – The hidden power of loyalty and facing down risks bigger than Deloitte05:35 – How do you keep policymakers, professors, and entrepreneurs moving together?10:34 – The stop-doing list: Skye’s ruthless system for switching hats daily15:06 – The radical transparency tactic that keeps remote teams accountable18:16 – What’s really at stake when culture fails, and no one steps up23:58 – Skye’s blueprint for replicable, world-class events—anywhere29:23 – Why firing people and failed partnerships still sting at the top34:18 – The “humane entrepreneurship” concept that rewrites how leaders show upAbout the GuestSkye Blanks is the Chief Operating Officer of the International Council for Small Business (ICSB), where he works closely with executive leadership to scale operations and support small and medium-sized enterprises globally. He is also the founder of Premo Cannabis and serves in advisory and board-level roles, bringing a hands-on operator’s perspective shaped by building and leading organizations. His work centers on execution, governance, and being an effective second-in-command.🔗 LinkedIn | WebsiteMentioned ResourcesTaylor & FrancisUN MSME DayJournal of Small Business ManagementNotionMoneyball (film)Dr. Ki-Chan Kim – “Humane Entrepreneurship”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: http://www.redirectcoo.com/
• Ep. 576- Tilt COO Taylor McLemore - How To Approach Leave Management and Organizational Performance 05.05.2026 41min

  What would your workplace look like if every single leave of absence became a chance to build legendary loyalty and turbocharge retention?Sivana Brewer sits down with Taylor McLemore, COO at Tilt, for a conversation that slices through HR noise and exposes the uncomfortable truth: most companies fumble leave policies and lose their best people as a result. This episode unpacks the hidden costs (and wild upsides) of leave done right.From the real-world pain operators feel managing compliance chaos, to how AI is shaking the industry, and the “roles, responsibilities, expectations” framework that creates lasting clarity, this is actionable COO gold.Miss this, and you risk bleeding talent, tanking culture, and getting steamrolled by change. Listen now for raw lessons, war stories, and tested tactics you won’t hear anywhere else.Timestamped Highlights00:40 – The brutal truth about why leave management is your hidden loyalty driver02:07 – The jaw-dropping time and complexity HR teams actually face08:20 – A career-changing moment: what empathetic leave really looks like13:16 – The overlooked ROI of doing leave brilliantly14:23 – Why Tilt planted the flag as the AI leader (and what that really means)16:43 – The four principles that keep AI both fast and safe inside HR22:40 – The surprisingly simple doc that ends CEO-COO confusion29:15 – The unexpected power of letting people define “winning” in their own roleAbout the GuestTaylor McLemore is the COO of Tilt, revolutionizing employee leave with empathy and technology. Taylor is the founder of the Human Potential Summit. Previously, he was an EIR at Stand Together. Taylor is a venture builder, scale operator, community connector, and investor. Taylor served on the Colorado Banking Board and the Board of Trustees for Colorado PERA. Previously, he launched and built the Techstars Workforce Development Accelerator as a Managing Director at Techstars. Taylor was the Co-Chair of the DAV National Veterans Entrepreneurship Council. He previously served as an advisor to SHRM Labs and sits on a number of startup boards. Previously, he was Managing Director of Able, a venture and product studio. While at Able, he was a co-founder and investment lead for Codeable, a coding school in Latin America. Taylor was the founder and a board director for Patriot Boot Camp, a nonprofit that supports military veteran and military spouse entrepreneurs. Patriot Boot Camp was acquired by DAV in 2021.🔗 LinkedIn | WebsiteMentioned ResourcesTechstarsRipplingPaycorPaylocityWorkdayRay Dalio – Weighted BelievabilitySOC 2 ComplianceShort-Term Disability (US HR context)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 bySTS Capital – A global M&A advisory firm helping entrepreneurs achieve maximum value when selling their business, with a focus on strategic buyers and life-changing exits.Learn more:https://stscapital.com
• Ep. 575 - Trevanna Tracks COO Selina Meere - How to Energize Culture and Deliver Reliable Results 30.04.2026 44min

  Ever wondered why one song can instantly give you chills… while another makes you feel nothing at all?In this episode, Selina Meere, COO of Trevanna Tracks, pulls back the curtain on the invisible system behind the music you feel in films, ads, and media. From navigating complex rights and scaling music operations for global brands to leading without a playbook, this conversation dives deep into what it really takes to operate at the intersection of creativity, technology, and leadership.They explore the realities of being a COO, managing elite teams, making high-stakes decisions, and building trust in environments where there are no clear answers.If you want to understand how world-class operators think, lead, and execute under pressure, don’t wait. The cost of staying reactive instead of strategic is too high. Hit play now for insights you won’t hear anywhere else.Timestamped Highlights[00:00] – The hidden force behind why certain songs instantly trigger emotion in movies and ads[02:14] – Why music licensing became exponentially more complex, and what most people don’t realize[04:21] – The “Excel breaking point” that led to building a completely new category in media[06:37] – From book publishing to COO, the unexpected career pivot that changed everything[11:00] – The moment she had to learn DevOps, Agile, and engineering… from scratch[13:40] – The leadership mistake most companies make during major internal transformations[17:11] – How top teams actually prioritize when every client thinks their request is urgent[19:01] – The hardest part of being a COO, and why there’s no such thing as a playbook[28:12] – The real way to build confidence when making big, high-risk decisions[31:54] – Why asking questions can quietly destroy trust, and how to fix itAbout the GuestSelina Meere is the COO of Trevanna Tracks, a pioneering music rights and workflow platform serving some of the largest media and entertainment companies in the world. With a background in publishing and PR, she has built a career partnering closely with founders to scale businesses, optimize operations, and drive growth across industries. Known for her adaptability and strategic thinking, Selina specializes in leading high-performance teams in complex, fast-evolving environments.🔗 LinkedIn | WebsiteMentioned ResourcesChief (Women’s Executive Network)Random HouseWarner (client reference)Apple (client reference)Leila HormoziAlex HormoziAbout 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/
• Ep. 574 - FAN FAVORITE | Mailchimp former Chief Operation Officer Sheldon Cummings – Watch How Resilient Leaders Win BIG Inside Corporate Giants 28.04.2026 41min

  Ever worried you’re missing your shot at breakthrough growth because your leadership team is stuck in old patterns?This episode is a raw look inside the mind of Sheldon Cummings, former Chief Operating Officer at Mailchimp and current President and General Manager at Smarsh, who’s steered brands across continents and navigated acquisition into one of the world’s most powerful tech companies. Cameron Herold digs deep into resilience, ruthless prioritization, and the magic of connecting culture to results, all delivered with a straight-shooter’s clarity. If you’re tired of shallow “success stories” and want the playbook for leading teams through uncertain times, this is your urgent reality check.Don’t wait for your competitors to outpace you. Listen now! The invisible skills (and mistakes) revealed here will save you from costly setbacks, wasted energy, and slow, silent failure. These exclusive insights aren’t recycled elsewhere. Your team (and your sanity) can’t afford to miss this.Timestamped Highlights[00:00] – The one moment that reset Sheldon Cummings’s entire career path… and how he engineered opportunity from chaos06:42 – How a bold toolkit-first mindset kept propelling him up—across continents, industries, and uncertain times11:07 – “Can you run a business you don’t ‘make’?” The surprising truth from global CPG frontlines17:05 – The #1 underdog advantage in modern marketing—why Mailchimp doubled down on it during COVID18:36 – What nobody tells you about integrating remote teams after a billion-dollar acquisition22:58 – Ruthless prioritization in product roadmap: When discipline trumps ideas (and keeps customers loyal)24:41 – Find the real numbers that matter: How top execs slice through data noise (and ignore 9,000 distractions)35:40 – How to unfreeze middle management and create instant buy-in during relentless changeAbout the GuestSheldon Cummings is the former Chief Operating Officer for Mailchimp. Before stepping into his leadership role at Mailchimp, he had a dual role as a VP Intuit Sales in addition to serving as Intuit’s Chief Diversity, Equity, and Inclusion Officer (CDEIO). Since joining Intuit in 2017, Sheldon has led a number of leadership positions across Intuit’s Sales, Marketing, Global Partnerships, and Global Operations teams. Prior to Intuit Sheldon has had a number of roles across industries and countries, including leading a European business for 6 years headquartered in Zurich, Switzerland. Sheldon, a native of New York City, graduated with a BA from Wesleyan University, and received his MBA from Northwestern University’s Kellogg School of Management with concentrations in Finance, Marketing, and Strategy. He is currently the President and General Manager of Smarsh.🔗 LinkedInMentioned ResourcesMailchimpIntuitQuickBooksTurboTaxKellogg School of Management (Northwestern)Wesleyan UniversityMcMaster-CarrKimberly-ClarkKraft FoodsMondelezHuggies (Kimberly-Clark brand)ZVV transit app (Zurich)Design for Delight (Intuit framework)Clayton State Technology Program (Mailchimp/Intuit community initiative)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.
• Ep. 573 - WEBTOON Global CFO and COO David Lee - Why Most Leaders Play Small… and How to Escape 23.04.2026 41min

  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.
• Ep. 572 - FAN FAVORITE | Sean Kim (HighLevel CPO, Former Kajabi President, Ex-Amazon, TikTok): Conquer Imposter Syndrome and Lead Powerfully 21.04.2026 36min

  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.
• Ep. 571 - Grindr Former COO Rick Marini - How to Spot A-Players and Deliver Big Results Fast 16.04.2026 44min

  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: http://www.redirectcoo.com/
• Ep. 570 - The Virtual Hub COO Arnold le Rutte - How Strong Systems Create Hopeful Results 14.04.2026 53min

  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.
• Ep. 569 - Pearl COO Ben Plomion - How Top COOs Crush Chaos and Build Pro Teams 09.04.2026 46min

  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/
• Ep. 568 - TextNow COO Lindsay Gibson - How to Rebuild Culture (and Yourself) in Crisis 07.04.2026 46min

  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.
• Ep. 567 - Contractor Foreman COO Marcus Hantla - How Top COOs Overcome Vulnerable Moments 02.04.2026 46min

  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/
• Ep. 566 - Virta Health COO Amit Shah - Exclusive Lessons from Scaling a Mission-Obsessed Team 31.03.2026 44min

  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.
• Ep. 565 - D1 Training COO Dan Murphy - How to Scale Smarter and Avoid Leadership Burnout 26.03.2026 43min

  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: http://www.redirectcoo.com/