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    Business

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

    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.

    Advertise

    Copyright: © Copyright 2024 Second in Command: The Chief Behind the Chief

    • Apple Podcasts
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    Latest Episodes:
    Ep. 581 - CoinMe COO Sung Choi - Life After Acquisition: Surprising Wins and Brutal Costs May 21, 2026
    Show notes

    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/cooassessment

    Timestamped Highlights

    00:06 – The brutal reality of CoinMe’s early hardware dreams

    11:10 – Why powering partners crushed owning infrastructure

    13:04 – “M&A is like polyamorous dating” and what nobody tells you

    17:14 – The tension of disclosure and keeping employees sane

    22:25 – A surprising pivot: from bitcoin hype to stablecoin utility

    26:29 – The regrets and rewards of abandoning office life

    30:26 – How “work from anywhere” delivers hidden productivity

    34:01 – Why AI is now their secret operating system

    44:23 – The one leadership skill every modern COO must master

    About the Guest

    Sung 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 | Website

    Mentioned Resources

    • Polygon Labs
    • Coinstar
    • Pantera Capital
    • Digital Currency Group (DCG)
    • Gemini (AI tool)
    • Claude (AI tool)
    • ChatGPT
    • iTex (formerly ubarter.com)
    • Goldman Sachs
    • OKRs framework

    Important Links

    • Connect with Cameron: Website | LinkedIn
    • Explore the COO Alliance - The World’s Leading Community for Seconds in Command
    • Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
    • Take 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 Delphi

    The 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 May 19, 2026
    Show notes

    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 Highlights

    00:33 – The unlikely airport arrival that rewired Jose’s confidence for life

    06:24 – The “self-directed team” principle that built a 40-year inner circle

    09:16 – Why leaders must channel Merlin, not the King, to win with teams

    11:18 – The brutal difference purpose makes when lives are on the line

    13:23 – What true CEO-COO alignment REALLY looks like behind closed doors

    16:44 – Underground, Battleground, Common Ground: The language that kills or creates culture

    20:12 – How AI quietly transforms operator decisions in real emergencies

    31:05 – The unspoken burden of leading a company where mistakes can cost lives

    About the Guest

    José Mejia isthe 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 | Website

    Mentioned Resources

    • IBM
    • Duke University
    • Lucent and Bell Labs
    • Andy Grove (former CEO of Intel; High Output Management book)
    • Soul on Fire (book and movie)
    • Magic Cabaret, Chicago
    • Slack
    • Google Docs

    About the Co-Host

    Lindsay 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 LinkedIn

    Important Links

    • Connect with Cameron: Website | LinkedIn
    • Explore the COO Alliance - The World’s Leading Community for Seconds in Command
    • Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
    • Take 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 Delphi

    The 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 May 14, 2026
    Show notes

    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.

    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/

    Timestamped Highlights

    06:12 – The real chaos of disaster recovery nobody tells you

    10:05 – Why chasing growth can sabotage your core business overnight

    14:05 – The unexpected curse of working with family

    17:00 – The radical communication exercise that finally changed everything

    22:29 – Brutal truths about enabling and hiring for potential

    27:15 – The moment Claudine Ripert stopped being a control freak

    30:06 – The shift from “majoring in the minors” to critical thinking

    41:46 – Why the right broker referral beats insurance programs every time

    About the Guest

    Claudine 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 | Website

    Mentioned Resources

    • Who by Geoff Smart
    • CAFE (Canadian Association of Family Enterprise)
    • Maslow’s Hierarchy of Needs
    • College Pro Painters
    • 1-800-GOT-JUNK
    • Gerber Auto Collision/Boyd Auto Body

    Important Links

    • Connect with Cameron: Website | LinkedIn
    • Explore the COO Alliance - The World’s Leading Community for Seconds in Command
    • Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
    • Take 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 Delphi

    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.

    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. 578 - Savannah Bananas President Jared Orton – How Fun Became the Ultimate Competitive Advantage May 12, 2026
    Show notes

    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 Highlights

    • 00:00 – Why telling fans “You can’t buy a ticket” made them desperate to get in
    • 03:34 – The culture playbook that turned baseball on its head
    • 07:59 – The brutal truth: fun was their only real competitive edge
    • 12:03 – The $15 all-you-can-eat gamble that shocked their market
    • 15:39 – How they engineer relentless fun without losing operational discipline
    • 20:44 – Why letting the wrong players walk is a proven culture win
    • 25:00 – The pandemic forced a do-or-die vision shift overnight
    • 34:00 – Their biggest tactical mistake and how it nearly cost everything

    About the Guest

    Jared 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 | Website

    Mentioned Resources

    • Vision Driven Leader by Michael Hyatt
    • Mastermind Talks (MMT)
    • Jim Collins – Good to Great, the “Hedgehog Concept”
    • Stephen Covey – 7 Habits of Highly Effective People
    • Banana Ball rules
    • Walt Disney World
    • Pixar (Toy Story creative strategy)

    Important Links

    • Connect with Cameron: Website | LinkedIn
    • Explore the COO Alliance - The World’s Leading Community for Seconds in Command
    • Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
    • Take 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 Delphi

    Note: 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 May 07, 2026
    Show notes

    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 Highlights

    00:31 – The “born operator” mindset that shaped a global COO

    02:36 – The hidden power of loyalty and facing down risks bigger than Deloitte

    05:35 – How do you keep policymakers, professors, and entrepreneurs moving together?

    10:34 – The stop-doing list: Skye’s ruthless system for switching hats daily

    15:06 – The radical transparency tactic that keeps remote teams accountable

    18:16 – What’s really at stake when culture fails, and no one steps up

    23:58 – Skye’s blueprint for replicable, world-class events—anywhere

    29:23 – Why firing people and failed partnerships still sting at the top

    34:18 – The “humane entrepreneurship” concept that rewrites how leaders show up

    About the Guest

    Skye 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 | Website

    Mentioned Resources

    • Taylor & Francis
    • UN MSME Day
    • Journal of Small Business Management
    • Notion
    • Moneyball (film)
    • Dr. Ki-Chan Kim – “Humane Entrepreneurship”

    About the Co-Host

    Sivana 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 LinkedIn

    Important Links

    • Connect with Cameron: Website | LinkedIn
    • Explore the COO Alliance - The World’s Leading Community for Seconds in Command
    • Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
    • Take 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 Delphi

    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.

    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 May 05, 2026
    Show notes

    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 Highlights

    00:40 – The brutal truth about why leave management is your hidden loyalty driver

    02:07 – The jaw-dropping time and complexity HR teams actually face

    08:20 – A career-changing moment: what empathetic leave really looks like

    13:16 – The overlooked ROI of doing leave brilliantly

    14:23 – 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 HR

    22:40 – The surprisingly simple doc that ends CEO-COO confusion

    29:15 – The unexpected power of letting people define “winning” in their own role

    About the Guest

    Taylor 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 | Website

    Mentioned Resources

    • Techstars
    • Rippling
    • Paycor
    • Paylocity
    • Workday
    • Ray Dalio – Weighted Believability
    • SOC 2 Compliance
    • Short-Term Disability (US HR context)

    About the Co-Host

    Sivana 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 LinkedIn

    Important Links

    • Connect with Cameron: Website | LinkedIn
    • Explore the COO Alliance - The World’s Leading Community for Seconds in Command
    • Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
    • Take 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 Delphi

    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.

    Sponsored by

    STS 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 Apr 30, 2026
    Show notes

    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.

    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

    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 it

    About the Guest

    Selina 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 | Website

    Mentioned Resources

    • Chief (Women’s Executive Network)
    • Random House
    • Warner (client reference)
    • Apple (client reference)
    • Leila Hormozi
    • Alex Hormozi

    About the Co-Host

    Sivana 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 LinkedIn

    Important Links

    • Connect with Cameron: Website | LinkedIn
    • Explore the COO Alliance - The World’s Leading Community for Seconds in Command
    • Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
    • Take 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 Delphi

    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.

    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. 574 - FAN FAVORITE | Mailchimp former Chief Operation Officer Sheldon Cummings – Watch How Resilient Leaders Win BIG Inside Corporate Giants Apr 28, 2026
    Show notes

    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 chaos
    • 06:42 – How a bold toolkit-first mindset kept propelling him up—across continents, industries, and uncertain times
    • 11:07 – “Can you run a business you don’t ‘make’?” The surprising truth from global CPG frontlines
    • 17:05 – The #1 underdog advantage in modern marketing—why Mailchimp doubled down on it during COVID
    • 18:36 – What nobody tells you about integrating remote teams after a billion-dollar acquisition
    • 22:58 – 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 change

    About the Guest

    Sheldon 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.

    🔗 LinkedIn

    Mentioned Resources

    • Mailchimp
    • Intuit
    • QuickBooks
    • TurboTax
    • Kellogg School of Management (Northwestern)
    • Wesleyan University
    • McMaster-Carr
    • Kimberly-Clark
    • Kraft Foods
    • Mondelez
    • Huggies (Kimberly-Clark brand)
    • ZVV transit app (Zurich)
    • Design for Delight (Intuit framework)
    • Clayton State Technology Program (Mailchimp/Intuit community initiative)

    Important Links

    • Connect with Cameron: Website | LinkedIn
    • Explore the COO Alliance - The World’s Leading Community for Seconds in Command
    • Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
    • Take 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 Delphi

    Note: 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 Apr 23, 2026
    Show notes

    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.

    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/

    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 innovators

    About the Guest

    David 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 | Website

    Mentioned Resources

    • Impossible Foods
    • Zynga
    • Best Buy
    • Rhode Island School of Design (RISD)
    • NASDAQ

    About the Co-Host

    Sivana 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 LinkedIn

    Important Links

    • Connect with Cameron: Website | LinkedIn
    • Explore the COO Alliance - The World’s Leading Community for Seconds in Command
    • Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
    • Take 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 Delphi

    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.

    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 Apr 21, 2026
    Show notes

    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 Highlights

    00:23 – Why Sean Kim said “hell no” to TikTok… at first. The surprising conversation that changed everything

    01:10 – “Discovery” is the real unlock… how it built TikTok’s domination and sparked Sean Kim’s obsession

    08:18 – What happens when you leave Amazon’s scale for pure startup chaos… scrappy desks, no process, and surviving the LA office

    09:24 – The secret power of the “doc writing” culture… how writing, not slides, became TikTok and Amazon’s unfair advantage

    12:24 – Ruthless speed… fail fast, double down faster, and outmaneuver every competitor. This is how TikTok really operates

    14:45 – Why Kajabi never bloats its teams… and how knowing exactly when to hire is a massive competitive edge

    17:13 – The impact calculator… predicting revenue, retention, and customer wins before a single feature ships

    25:40 – How to crush “feature creep” and avoid turning your SaaS into a Frankenstein’s monster

    About the Guest

    Sean 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 Resources

    • TikTok
    • Amazon Prime
    • Bulletproof Coffee
    • Dave Asprey
    • ByteDance
    • The “doc writing” process (Amazon framework)
    • Impact calculator for product decisions

    Important Links

    • Connect with Cameron: Website | LinkedIn
    • Explore the COO Alliance - The World’s Leading Community for Seconds in Command
    • Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
    • Take 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 Delphi

    Note: 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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