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

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...

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 mark...

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 vis...

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 C...

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 whe...

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 metr...

Ever question if you’re truly moving the needle in a high-stakes, fast-growth role or just treading water in chaos? In this unfiltered replay, Cameron Herold gets radically real with Asana’s COO, Anne Raimondi, a powerhouse operator with a track record scaling iconic SaaS brands from eBay to Zendesk. Their candid conversation delivers hard-hitting truths and breakthrough strategies for COOs, VPs o...

When was the last time you felt your vision misunderstood, your partnership undervalued, or your operational roadmap tangled? If you’re a COO wrestling with translating big ideas into real impact, this conversation is your lifeline. Sivana Brewer welcomes Stephanie Kauffman, Chief Operating Officer at Melanoma Research Alliance, for an urgent episode that lifts the veil on what actually moves the...

Ever felt like you’re carrying the weight of growth, but struggling to shift your company from band-aids to real, sustainable breakthroughs? Meet Nicki Baty, COO at Freshpet, who’s rewriting the playbook for second-in-command leadership inside a rocketship culture. In this revealing conversation, Nicki Baty opens up to host Sivana Brewer about pioneering a COO role from scratch, installing trust (...

What if the biggest threat to your company’s growth is how you show up every day—burned out, distracted, or just going through the motions? Most COOs know the cost of chaos, but few stop to ask what’s driving it inside themselves. Enter Sunil Rajasekar, former Presiden t and CTO of Mindbody , who sits down with Cameron Herold for a no-holds-barred conversation about burnout, resilience, and buildi...

Are you trapped in operational chaos, fighting burnout, and searching for a formula that actually scales? You’re not alone. This electrifying episode features Guillaume Bouvard , Co-founder , COO and CMO of Extend , as he sits down with Sivana Brewer to reveal the real-life victories and invisible battles behind explosive fintech growth. From his unusual rise at American Express to building a team...

What if your next breakthrough isn’t more hustle, but ruthless focus on what actually matters? Scott Levy , Fractional COO of ResultMaps , joins Sivana Brewer for a candid, zero-fluff conversation on why most CEOs and COOs are drowning in distraction and what separates “second in command” leaders who skyrocket growth from those stuck grinding. They pull apart why ambitious teams spiral into task o...

Are you overwhelmed by nonstop chaos, endless stakeholder demands, or the fear you’ll break while scaling up? This episode delivers urgent answers for every COO, integrator, and senior ops leader pushing to get their head above water. Cameron Herold sits down with Kelly Knight, President and Integrator of EOS Worldwide, for a rare, candid look at the systems and mindset that power explosive growth...

What if you could transform a team of rookies into high-performing, loyal leaders and stay sane in the process? This episode delivers an unfiltered look inside the mind of Richard Comitz , Chief Operating Officer of American Corporate Partners, a West Point PhD and retired Army Lieutenant Colonel now leading one of America’s most mission-driven nonprofits. He sits down with Narrator to unpack the...

What if the difference between scaling up and burning out comes down to just one overlooked decision you make today? In this exclusive Second in Command episode, Cameron Herold sits down with Jon McNeill, former President of Tesla and COO of Lyft , and current CEO and Co-Founder of DVx Ventures, for a bold, eye-opening deep dive into the raw realities of being second in command at companies that r...

Ever wonder why some COOs scale businesses to legendary heights while others get swallowed by chaos and politics? If you’re craving clarity, confidence, and uncommon edge in your second-in-command role, this Fan Favorite episode is your wake-up call. Cameron Herold sits down with Matt MacInnis, COO of Rippling and co-founder of Inkling , for a raw, actionable conversation about the real challenges...

Feeling the pressure to scale but terrified of losing your best people, or watching team morale dissolve as your business grows? This episode, guest host Sivana Brewer gets real with Isaac Tobelen, current CMO at Springs Rejuvenation and seasoned COO, on the inside challenges of recruiting, retaining, and motivating talent in rapid-growth settings. Isaac shares proven systems for hiring culture-al...

Ever wondered how legendary operations leaders onboard 800 seasonal hires for world-class performance in just 30 minutes? What if your biggest edge wasn’t tech, but radical clarity, proven systems, and the courage to democratize what most companies hide? In this revealing conversation, guest host Sivana Brewer sits down with Tom Root, Managing Partner at Zingerman’s Mail Order and a driving force...

Struggling to scale your law firm or lead expert teams without burning out or losing your edge? You’re not alone. In this episode, Cameron Herold brings you an unfiltered, radically honest conversation with Dan Cuneo, COO of Melone Hatley. Dan reveals the surprising truth behind law firm growth, why lawyers love culture but hate change, and the communication systems driving results in a multi-offi...

Are you tired of chaotic operations, burned-out teams, and the relentless pressure to execute big visions without breaking yourself in the process? In this can’t-miss fan favorite episode, Cameron Herold goes deep with Griff Long, former COO of Orangetheory Fitness, a leader who’s transformed personal growth and business results at some of America’s top brands. If you’re a second-in-command, exhau...

Ever wonder why some companies feel magnetic while others are just…a job? If you believe company culture is fluff, this conversation will put you on your heels. Cameron Herold sits down with Amy Emberling, Managing Partner of the legendary Zingerman’s Bakehouse—a $16M+ artisan bakery with a cult following and a blueprint for employee loyalty big brands envy. Together, they pull back the curtain on...

Are you tired of feeling trapped in the chaos of scaling, with too many projects and not enough clarity on what actually drives growth? In this episode, host Cameron Herold sits down with Josh Post, COO of Cabochon Group and longtime COO Alliance member, for an emotionally raw, practical conversation about breaking out of operational overwhelm. Josh reveals how he went from reluctant family busine...

What if the real key to scaling your business isn’t a revolutionary product, but your ability to build a culture where “weirdness” is an asset and radical respect transforms politics into partnership? In this electric episode, Cameron Herold sits down with John McDonald, Chief Operating Officer at Poshmark , to unpack how one of the world’s most beloved marketplaces keeps growing in spite of Golia...

What if the most valuable currency in your career isn’t money, but authentic relationships nobody can take away? In this urgent episode, guest host Sivana Brewer digs deep with John Rubino, COO and founder of JID Investments and a US naval aviator turned business leader. Together, they unravel how military discipline, open-book honesty, and relentless connection-building are the forgotten keys to...

Are you secretly worried your growth will wreck the “family” vibe in your business or that tighter systems will make top talent leave? In this episode, Sivana Brewer interviews Erica Wright, COO of VRA Realty, whose systems-first playbook catapulted the brokerage from 85 to 115 agents, spanning five states. They dig into the raw truth of building infrastructure for explosive scale (without losing...