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

In this episode, Cameron sits down with Brett Bruggeman, Executive Vice President and COO of Land O’Lakes, a 104-year-old, $16B cooperative spanning dairy foods, animal nutrition, and crop inputs. Brett shares how Land O’Lakes manages scale across 20 business units, supports more than 4,000 cooperative owners, and touches half of America’s farmland.He and Cameron dig into the cooperative model, growth challenges in shrinking markets, how the company is driving new productivity for farmers, and their bold new initiative that partners with retail owners to invest in late-stage ag-tech. Brett also talks about outside-in thinking, the power of data, how to stay ahead of the customer, and why the future of agriculture requires both AI and human EQ.If you’re a COO navigating large-team complexity, shifting markets, or innovation inside a legacy organization, this conversation is a masterclass in clarity, discipline, and strategic focus.Timestamped Highlights00:00 Brett and Cameron kick off the conversation (with a quick cameo from Brett’s comms lead, John).01:03 How Brett discovered the podcast and the purpose of “the COO story.”03:30 Land O’Lakes overview: 104-year history, cooperative structure, and national footprint.07:14 The company’s roots: dairy farmers searching for a market for cream.08:26 How Land O’Lakes evolved into dairy, animal nutrition, and crop inputs.10:24 Purina brand clarification: Land O’Lakes vs. Nestlé internationally.10:44 Revenue breakdown across business units.12:00 How Brett avoids getting pulled into every detail while leading a massive enterprise.14:10 How outside-in thinking reshaped corporate strategy.15:17 The “vital few” → the three-or-four priorities that guide the entire company.16:49 The six transformation “big bets.”18:46 Becoming a data-first company: insights, segmentation, and new markets.20:29 The strategic questions Land O’Lakes uses to break stagnation.22:45 Their stance on hybrid work and why face-to-face still matters.25:05 Growth challenges: farmers under pressure, shrinking markets, and opportunities.26:05 Introducing AgRogue: the new retail growth fund (70–100M) to invest in late-stage ag-tech.27:39 Why partnering with retail owners creates stronger market access.28:17 What a cooperative actually is and how it differs from other business models.31:39 How 4,000 owners create loyalty, but not complacency.33:31 Why aligning retail owners with Land O’Lakes creates predictable innovation adoption.36:51 How AI and predictive models are transforming supply chain, waste, and productivity.38:37 Three AI goals: target growth, eliminate waste, improve customer experience.40:55 How Land O’Lakes approaches AI responsibly (and without getting “over their skis”).42:37 What Brett is working on personally as a leader: presence, change management, results.47:28 Advice to his younger self: ask better questions, seek mentors, take international roles.Resources & MentionsPurina (livestock feed brand)WinField (crop inputs brand)Microsoft (AI and data initiatives)AgRogue (Land O’Lakes + retail owner growth fund)Radicle (ag-tech investment partner)Circana (retail data source, referenced as...

In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Matthew Rathje, Chief Operating Officer of TrueNorth Companies and long-time member of the COO Alliance.From starting in payroll and claims management to leading operations for a $165M insurance and professional services firm, Matt shares his journey of scaling from the ground up, balancing structure, culture, and human leadership. He offers practical insights on bringing clarity and accountability to fast-growing organizations, structuring meetings that actually move the needle, and building trust without falling into “artificial harmony.”Matt also opens up about navigating personal and professional adversity, from weathering the 2020 derecho storm that destroyed his family’s home, to leading through COVID-19, and how those experiences shaped his leadership philosophy rooted in humility, collaboration, and optimism.Timestamped Highlights[00:01:20] – Matt’s journey at TrueNorth and how he helped the company grow from a local firm to a $165M organization.[00:05:16] – Lessons from moving between individual contributor and leadership roles.[00:07:00] – How TrueNorth’s leadership transition inspired a more unified executive vision.[00:09:20] – Preparing to step into the COO role and finding mentors in the process.[00:10:44] – Why Matt joined the COO Alliance and what he learned from peers in other industries.[00:13:00] – Building clarity and accountability through RIMs and RIOs (Relatable Impact Metrics & Objectives).[00:15:00] – Starting TrueNorth’s organizational health journey with Patrick Lencioni’s Table Group.[00:17:34] – How Lencioni’s framework helped the team prioritize what’s most important right now.[00:18:46] – Team effectiveness workshops and how vulnerability-based trust builds healthy organizations.[00:20:35] – How to identify “artificial harmony” and address it before it erodes team commitment.[00:24:32] – Balancing collaboration with decisive leadership.[00:26:03] – Structuring meetings for clarity, speed, and results.[00:29:40] – How personal adversity (a devastating storm) strengthened Matt’s leadership perspective.[00:33:54] – Leading with empathy, gratitude, and perspective through crisis.[00:38:52] – Building trust and vulnerability across teams.[00:40:31] – Strengthening the CEO-COO relationship and defining complementary strengths.[00:42:42] – Using Vivid Vision to align the entire company around purpose and feeling.[00:46:14] – Launching The TrueNorth Way: the company’s roadmap for a world-class client experience.Resources & MentionsThe Apple Experience by Carmine GalloUnreasonable Hospitality by Will GuidaraMeetings Suck by Cameron HeroldThe Five Dysfunctions of a Team by Patrick Lencioni (and the related Five Behaviors of a Cohesive Team framework)About the GuestMatthew Rathje is the Chief Operating Officer of TrueNorth Companies, a Midwest-based insurance and professional services firm dedicated to protecting and maximizing its clients’ assets, resources, and opportunities.Since joining TrueNorth over a decade ago,...

In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Dr. Melonie Boone, Chief Operating Officer of Edesia Nutrition, a Rhode Island–based nonprofit on a mission to end childhood malnutrition worldwide.Dr. Boone shares her inspiring journey from corporate HR and executive consulting to joining a purpose-driven organization where every product saves lives. She opens up about leaving her consulting career to relocate her family and help Edesia scale globally while staying rooted in its humanitarian mission.Together, Sivana and Melonie explore what it means to lead in a business where the stakes are life and death, balancing operational excellence with empathy, trust, and resilience. From creating healthy CEO-COO dynamics to rebuilding confidence after crisis, she offers grounded advice for leaders who want to make impact and results coexist.Timestamped Highlights[00:02:31] – Dr. Boone explains Edesia Nutrition’s mission to eradicate malnutrition and how each box of product saves a child’s life.[00:04:29] – The personal loss that inspired her to pursue work with deeper purpose.[00:06:27] – How consulting for Edesia’s CEO turned into a full-time COO opportunity.[00:08:09] – Combining her lifelong drive to lead with her mother’s legacy of service.[00:10:14] – What challenges she was first hired to solve and how her HR and strategy background helped.[00:13:13] – Transitioning from consultant to COO and setting early “ground rules” for success.[00:15:00] – Dividing responsibilities with the founder and managing blurred lines gracefully.[00:16:20] – Facing two major business disruptions in her first six months on the job.[00:18:47] – Learning to adapt her leadership style during crises and rebuild trust.[00:20:18] – The power of transparency and “fighting together” with the CEO.[00:22:29] – How her four academic degrees shaped her approach to leadership.[00:24:08] – The lesson behind “anyone can show the numbers, but what do they mean?”[00:26:05] – Knowing which “Melonie” to bring into each meeting—coach, operator, or psychologist.[00:27:28] – How she keeps the pulse across 14 departments with weekly updates and morale checks.[00:31:29] – Using technology and HRIS tools to streamline communication and one-on-ones.[00:34:18] – Building cross-functional buy-in before making any system change.[00:36:50] – Tracking team morale and staying intentionally visible to every shift.[00:38:42] – Leading with authenticity as an introvert in a people-driven culture.[00:41:26] – Creating connection and fun through culture rituals, bingo, and bagel Tuesdays.[00:44:43] – What’s ahead: a 100,000 sq ft expansion, global growth, and personal goals for joy and balance.[00:47:00] – Her advice for aspiring COOs, current operators, and CEOs hiring their “number two.”Resources & MentionsEdesia Nutrition Plumpy’Nut® – Edesia’s flagship product saving children worldwideChildren Can’t Wait Campaign – Donate HEROic Leadership by Dr. Melonie BoonePaycor HRIS – Tool for one-on-ones, performance, and team engagementAbout the GuestDr. Melonie Boone is the Chief Operating Officer of Edesia Nutrition, a global...

In this Fan Favorite episode of the Second in Command Podcast, Cameron Herold speaks with Anna Collins, President and COO of Bulletproof, the globally recognized brand behind Bulletproof Coffee, supplements, and biohacking products designed to help people perform better, think faster, and live healthier lives. She is also a Board Member of Ladies Who Launch.Before joining Bulletproof, Anna led multi-billion-dollar businesses at Amazon, Microsoft, and CVS Health, bringing a data-driven, operational mindset to every stage of growth. In this conversation, she reveals how she helped Bulletproof evolve from a niche “biohacker” brand into a household name—streamlining operations, tightening focus, and scaling omnichannel distribution without losing its visionary edge.Anna also shares her leadership principles, from managing a founder with 100 ideas a day to running metrics-driven weekly business reviews that keep innovation grounded in reality. Her insights bridge the gap between entrepreneurial chaos and corporate discipline, showing how great COOs turn vision into execution.Timestamped Highlights[00:00:00] – Cameron introduces this episode as one of the most downloaded in show history.[00:01:14] – Anna’s career journey: from Microsoft and Amazon to joining Bulletproof.[00:03:52] – Why she left Amazon Prime for a mission-driven brand.[00:05:36] – What convinced her Bulletproof wasn’t just a fad—but a real performance enhancer.[00:06:23] – Partnering with Dave Asprey: defining roles between visionary and operator.[00:07:18] – The challenge of narrowing focus when everything looks like a good idea.[00:08:54] – Bringing Amazon’s frameworks—tenets, principles, and data mechanisms—into Bulletproof.[00:10:07] – How structure helped Dave trust the team and delegate.[00:10:26] – Shutting down international markets and cutting SKUs to simplify growth.[00:11:59] – Expanding into Amazon marketplace and corporate distribution channels.[00:13:28] – Convincing the founder to “grow beyond the core biohacker.”[00:17:00] – Managing an idea-rich founder without stifling creativity.[00:18:37] – Anna’s leadership philosophy: define reality, create possibility, say thank you.[00:21:00] – Rebuilding Bulletproof’s vision, mission, and values for clarity and culture.[00:24:20] – Weekly Business Reviews: the data-driven rhythm behind execution.[00:30:32] – How Anna divides her focus across key stakeholders—customers, team, and growth.[00:36:35] – Simplifying the Bulletproof brand for mainstream accessibility.[00:38:00] – Where she struggles as a leader—and the balance between speed and empathy.[00:42:33] – The advice she’d give her 21-year-old self: don’t take it all so seriously.About the GuestAnna Collins is the President and COO of Bulletproof overseeing strategy, operations, and omnichannel growth for the globally recognized biohacking brand. Previously, she led billion-dollar initiatives at Amazon, where she managed global Prime membership programs, and at Microsoft, where she built the search advertising business from concept to $1.6B in revenue. She is also a Board Member of Ladies Who Launch.A Harvard MBA and transformational leader, Anna specializes in building scalable systems that bridge creative vision with operational discipline. At Bulletproof, she’s helped expand the company from its core biohacker audience to a broader wellness market—making human optimization accessible to everyone.🔗 LinkedIn Resources & MentionsBulletproof 

In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Daniel Quinonez, Chief Operating Officer of the Plumbing-Heating-Cooling Contractors Association (PHCC) — one of the oldest trade associations in the United States, founded nearly 140 years ago.Daniel shares how this long-standing organization is transforming to meet the modern era while honoring its heritage. From training apprentices who go on to run multimillion-dollar companies, to integrating AI and new tech tools into the trades, the PHCC is proving that innovation and tradition can coexist.He also opens up about leadership lessons from his own journey, from mopping floors at his father’s bar to leading a national $30M organization, and how his personal mantra, “Be nice,” has shaped his management style, his culture, and his success.If you lead a legacy business, manage a growing team, or want to understand how blue-collar industries are embracing technology, this episode offers both inspiration and strategy.Timestamped Highlights[00:01:00] – The PHCC’s 140-year history and why plumbing is a pillar of public health.[00:02:40] – How the industry came together to standardize clean water systems in the 1920s.[00:03:44] – What PHCC offers its members today: education, licensing, and community.[00:05:08] – From one truck to $10M: stories of self-made contractors in the trades.[00:06:14] – Why nearly every successful owner started as a hands-on apprentice.[00:08:00] – How AI is transforming the trades and why it’s an ally, not a threat.[00:09:34] – Changing perceptions: convincing parents that the trades are a smart career path.[00:10:39] – The rise of entrepreneurship and financial freedom in plumbing and HVAC.[00:11:42] – Daniel’s own career path from government and lobbying to COO.[00:13:57] – Becoming the first COO in PHCC’s 140-year history.[00:15:25] – Helping a century-old organization modernize its operations and systems.[00:17:03] – Growing membership and education as PHCC’s two strategic pillars.[00:18:55] – The PHCC Online Academy: 15,000 students and counting.[00:21:00] – The challenge of evolving legacy culture and systems in long-standing institutions.[00:22:30] – Why more contractors are creating COO roles for succession planning.[00:25:17] – Family businesses, private equity, and the changing face of ownership.[00:27:56] – Daniel’s leadership mantra: “Be nice.”[00:33:38] – Balancing kindness with accountability and setting measurable goals.[00:35:00] – Building buy-in and bringing staff along during organizational change.[00:39:00] – Teaching business finance and leadership to new COOs in the trades.[00:43:36] – Daniel’s excitement for PHCC Connect 2024 and the next generation of apprentices.Resources & MentionsPHCC – Plumbing-Heating-Cooling Contractors AssociationPHCC Academy – Online education and apprenticeship trainingQuality Service Contractors (PHCC Program) – Business coaching for contractorsFederated Insurance – PHCC partner for business succession planningSkillsUSA & WorldSkills Competitions – Annual events supporting young tradespeopleAbout the GuestDaniel Quinonez is...

In this powerful episode of the Second in Command Podcast, co-host Sivana Brewer sits down with Brittany Dunn, COO and co-founder of Safe House Project, a national nonprofit dedicated to eradicating human trafficking in the United States.Brittany shares the remarkable story of how she and her co-founder built Safe House Project from an idea into a nationwide movement, launching a full organization in just 90 days while balancing motherhood, military life, and a mission to save lives.She discusses how her background in international business and M&A shaped her operational mindset, and how she’s using corporate systems to solve one of the world’s most complex humanitarian challenges. From developing Simply Report, a tech platform helping identify trafficking cases, to fostering a trauma-informed team culture, Brittany offers a masterclass in leadership under pressure, emotional resilience, and purpose-driven innovation.Timestamped Highlights[00:01:00] – Brittany shares the mission behind Safe House Project and how it began.[00:02:15] – Only 100 safe house beds existed for 300,000 trafficked kids—why resources were so scarce.[00:04:26] – How two military spouses built a national nonprofit in 90 days.[00:06:01] – Why they launched nationally instead of locally (and how it changed everything).[00:08:00] – A day in the life: policy, survivor support, sting operations, and leadership.[00:10:20] – The corporate skills that transferred and the ones that didn’t.[00:12:17] – Balancing strategy with empathy: why people aren’t “projects.”[00:13:01] – Hiring survivors to co-create programs that work in real life.[00:15:27] – The emotional weight of leading in trauma-informed work.[00:17:14] – Launching Simply Report, a new tech platform for anonymous trafficking tips.[00:19:00] – The behavioral algorithm behind Simply Report and how it works.[00:21:17] – The power of partnerships and why Brittany took every call early on.[00:22:41] – Preventing burnout: clarity, communication, and individualized care.[00:25:37] – Inside her relationship with her co-founder and how they model healthy conflict.[00:29:23] – Building a culture of trust, ownership, and open dialogue (“Cuss and Discuss”).[00:34:05] – How Safe House Project hires intentionally and why cultural fit matters most.[00:36:10] – The art of letting go: why firing fast protects mission and morale.[00:37:30] – A recent setback and how the team turned disappointment into innovation.[00:40:18] – Choosing integrity over comfort: giving back salaries during COVID to keep promises.[00:42:01] – Daily rhythms that keep Brittany grounded in hard seasons.[00:43:23] – The next big challenge: state-level adoption of Simply Report.[00:44:13] – A hopeful look ahead: documentary, podcast, and shifting public awareness.Resources & MentionsSafe House ProjectSimply Report App (iOS & Android) – Anonymous reporting tool for human...

In this episode of the Second in Command Podcast, co-host Sivana Brewer chats with Will Smith, COO and Managing Partner of Lone Star Pups, a multi-location Dogtopia franchise with 15 stores across San Antonio and Denver.Will shares how he’s scaled his team from zero to 140 employees in just a few years by leading with servant leadership, radical transparency, and a simple but powerful formula: Time + Trust = Influence.From teaching his staff about personal finance to running anonymous team surveys and writing heartfelt newsletters himself, Will breaks down how he creates a workplace where people feel seen, supported, and connected to the company’s mission. He also dives into financial literacy and why understanding money, personally and professionally, is the missing link for many leaders.Whether you’re managing a large service team or growing a people-first brand, this episode is packed with actionable leadership and financial principles that can transform both your team and your bottom line.Timestamped Highlights[00:04:15] – How Lone Star Pups began as a post-COVID passion project.[00:05:47] – The story behind Will’s partnership with his CEO, Devin.[00:07:43] – Building trust by adding value—not ego—to leadership.[00:09:19] – Why Will left a 30-year hospitality career to run a dog business.[00:11:00] – Making decisions that impact 140 people every day.[00:12:00] – Servant leadership in action: clearing plates, fixing walls, setting culture.[00:13:34] – How Time + Trust = Influence became the company’s core formula.[00:16:10] – What Will learned from his first company-wide employee survey.[00:17:00] – How monthly newsletters create connection and clarity.[00:19:10] – The truth about communication—why “no one ever over-communicated.”[00:25:20] – The meaning behind Watering Your Bamboo and why patience drives growth.[00:27:26] – How Will learned financial discipline from his grandfather.[00:29:00] – Teaching personal finance to staff—and why it improves retention.[00:31:36] – “Canary Metrics”: a system to track the financial health of each location.[00:33:49] – Why every manager must learn to write their own P&L variances.[00:35:00] – The link between personal spending habits and leadership performance.[00:40:35] – Helping the next generation reclaim their time, focus, and financial control.[00:41:15] – What’s next: growth, teaching, and giving back.Resources & MentionsLone Star Pups, LLC Dogtopia Watering Your Bamboo by Greg BellThe 80-10-10 Rule – Will’s personal finance framework (80% bills, 10% savings, 10% giving)The Speed of Trust by Stephen M.R. Coveya...

In this episode of the Second in Command Podcast, Cameron Herold sits down with Ebert Grobler, COO and co-founder of Ruby Digital, one of South Africa’s top-ranked digital agencies now expanding across the globe.Ebert, who is a COO Alliance member, shares how his company has achieved near-perfect team retention and why their internal mantra—“Grow People, Grow Global, Grow Profit”—has fueled both performance and culture. From developing a system called The Ruby Way to empowering every team member to operate like an entrepreneur, Ebert breaks down how Ruby Digital builds sustainable high performance without burnout.He also explains how they’ve turned retention, trust, and human connection into a competitive advantage in a saturated market and why premium service is still one of the rarest differentiators in the U.S. marketing landscape.Timestamped Highlights [00:01:45] – Why Ruby Digital is expanding from South Africa into the U.S. [00:05:25] – The surprising gap in the U.S. market: quality and retention. [00:08:12] – How Ruby Digital achieves 95–100% staff retention. [00:10:20] – Creating “The Ruby Way”: an operating system built on trust. [00:12:45] – Letting employees act like entrepreneurs without the risk. [00:16:00] – “Step Up”: the six-month advancement model that keeps people growing. [00:18:30] – Guardrails against burnout: scorecards, balance wheels, and wellbeing KPIs. [00:22:40] – Why culture drives premium client delivery. [00:25:05] – How Ebert measures success: Grow People → Grow Global → Grow Profit. [00:27:15] – Ruby’s philosophy: manage risk, not just marketing. [00:30:10] – B2B growth: focusing on long-term relationships, not quick wins. [00:33:25] – The “SMC client” model—serving sophisticated, mature companies. [00:36:10] – How much companies should invest in marketing (and why most don’t). [00:41:10] – Ruby’s 15% marketing reinvestment and in-house client mindset. [00:45:30] – Turning unused leads into referral revenue. [00:48:10] – The biggest lesson from failure: trust is earned, not given.Resources & MentionsSmart Marketing 2.0 Podcast – Co-hosted by Ebert GroblerScaling Up by Verne HarnishGood to Great by Jim CollinsAbout the GuestEbert Grobler is the COO and co-founder of Ruby Digital, a global performance marketing agency headquartered in South Africa with hubs in the U.K. and U.S. A former communication-science student turned “human-systems engineer,” Ebert is known for creating organizational models that blend business growth with human sustainability. Under his leadership, Ruby Digital has been recognized as one of the Top 20 Companies to Work For in South Africa by the U.K. Sunday Times and continues to redefine what it means to run a people-first, performance-driven company.🔗 LinkedIn |

In this episode of the Second in Command Podcast, guest co-host Sivana Brewer (Fractional COO for Remote Teams and former COO at Closers.io) sits down with Cory Raggi, COO of 1RDG The Financial Center, to talk about leading with empathy, navigating change, and building trust in teams both large and small.Cory shares her journey from leading HR at a 15,000-person company to stepping into her first COO role at a fast-growing 80-person firm. She opens up about how she learned to adapt, communicate, and stay grounded in high-pressure situations and the three core practices that help her regulate stress and lead with clarity.From learning to “roll on the edge” between people and performance to replacing stress with self-awareness, this conversation is packed with real-world leadership lessons for operators who want to grow without burning out.Timestamped Highlights[00:02:00] – How Cory went from HR leader to unexpected COO.[00:03:00] – Redefining what a COO really does (and doesn’t do).[00:06:26] – “Right people, right seats”: her mantra for solving every problem.[00:08:12] – Building trust with the CEO and learning to push back.[00:10:21] – Deprogramming corporate habits in a smaller company.[00:13:07] – Leading teams without being the technical expert.[00:17:13] – Building fast trust through humility and honest communication.[00:19:25] – The mirror test: checking your own leadership energy first.[00:22:00] – Balancing people and business why great leaders “roll on the rim.”[00:23:40] – Running effective meetings that actually serve their purpose.[00:28:16] – Leadership breakdowns most middle managers make.[00:33:13] – How Cory learned to stay calm and centered under pressure.[00:36:49] – The one-next-right-thing method for managing stress.[00:42:00] – The isolation of being a COO—and how to find your support system.[00:47:16] – What’s next for Cory personally and professionally?About the GuestCory Raggi, SHRM-SCP is the Chief Operating Officer of 1RDG The Financial Center, a company providing integrated accounting, payroll, benefits, and wealth management solutions for business owners. With a background in HR and organizational leadership, Cory blends people-first management with operational structure, helping teams stay aligned, communicative, and focused through growth.🔗 LinkedIn | Website | Podcast | LinktreeResources & MentionsThe Speed of Trust by Stephen M.R. CoveyCrucial Conversations by Patterson, Grenny, McMillan & SwitzlerMeetings Suck by Cameron HeroldEmotional...

In this Fan Favorite episode of the Second in Command Podcast, Cameron Herold sits down with Sarah Jones Simmer, former COO of Bumble, to explore how the company scaled from an empowering dating app into a billion-dollar global social platform redefining connection and kindness online.Sarah shares her journey from investment management to leading one of the fastest-growing social networking brands in the world. She opens up about working alongside visionary founder Whitney Wolfe Herd, expanding into markets like India, building culture-first teams, and reimagining leadership through empathy and purpose.From balancing motherhood and executive leadership to driving global expansion and shaping company culture, Sarah’s story offers an inspiring look at what it means to lead with both strength and softness.About the GuestSarah Jones Simmer is a seasoned business leader and former Chief Operating Officer of Bumble, where she helped scale the brand to over 50 million users worldwide. With a background in investment and strategy consulting, Sarah has built her career around mission-driven leadership, global expansion, and empowering women in business.🔗 LinkedIn | WebsiteResources & MentionsSerena Williams x Bumble Super Bowl CampaignAdam Grant – Organizational Psychologist and AuthorKolbe Profile (KOLBE A)TEDWomen ConferenceImportant 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.

In this episode of the Second in Command Podcast, Cameron Herold speaks with Brent Hagan, Chief Supply Chain Officer at Lob, a direct mail automation platform delivering billions of personalized mail pieces every year.Brent shares how he helped a 12-year-old startup kick off its “second act” by transforming complex logistics into scalable systems powered by technology and disciplined leadership. He opens up about developing next-generation leaders, learning to balance autonomy with accountability, and why the best operators focus less on “doing” and more on developing people who can think for themselves.From saying yes to opportunity to mastering feedback and context-switching, Brent breaks down how to lead through clarity, consistency, and reflection - and why great COOs act as both a shock absorber and a multiplier for the entire organization.Resources & MentionsLobUSPS (United States Postal Service) Amazon Discover Insights ProgramWharton Executive EducationPurdue UniversityInvest In Your Leaders Online CourseAbout the GuestBrent Hagan is the Chief Supply Chain Officer at Lob, overseeing logistics, vendor partnerships, and operational excellence for one of the fastest-growing direct mail automation companies in the U.S. A former Amazon leader and Wharton executive education graduate, Brent specializes in scaling operational systems, building resilient teams, and turning feedback into a strategic advantage.🔗 LinkedIn | WebsiteImportant 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 Delphi

What does it take to help build one of the most influential e-commerce companies in the world?In this Fan Favorite episode, Cameron Herold sits down with Harley Finkelstein, President and COO of Shopify, to revisit one of the most downloaded and talked-about conversations in the show’s history.Harley shares his journey from law school student to serial entrepreneur to becoming the operational powerhouse behind Shopify’s global rise. He opens up about working alongside founder Tobias Lütke, building the company’s culture from the inside out, and leading through rapid growth and constant reinvention.Whether you’re scaling a startup or steering a billion-dollar brand, Harley’s insights on leadership, culture, and staying grounded in the middle of explosive success will challenge and inspire you.About the GuestHarley Finkelstein is the President and Chief Operating Officer of Shopify, where he’s played a pivotal role in scaling the company from startup to a global leader in e-commerce. A serial entrepreneur and public speaker, Harley is also on the board of C100, an advisor to major venture funds, and a familiar face as a dragon on CBC’s Dragons’ Den.🔗 LinkedIn | WebsiteResources & MentionsGood to Great by Jim CollinsThe Misunderstood Role of the COO – Harvard Business ReviewRocket Fuel by Gino WickmanRiding Shotgun: The Role of the COO by Nathan Bennett & Stephen MilesMaker’s Schedule, Manager’s Schedule – Paul Graham essayImportant 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....

What really separates a COO who keeps the lights on from one who drives exponential growth?In this episode, Cameron sits down with Imad Jbara, COO of L2 Infinite Insurance and former COO of WoJo Media, who transformed a company’s client retention from 20% to 80% in just six months. Together, they unpack how COOs can build trust, fire with confidence, elevate leaders, and use systems to scale companies without chaos.From the painful lessons of firing too aggressively to the wisdom of patient onboarding and leveraging AI, Imad shares the unfiltered truth about what it really takes to succeed as a second in command.If you’re tired of firefighting and want proven systems to grow your company with less chaos, you can’t afford to skip this episode. Listen now for exclusive insights you won’t hear anywhere else.About the GuestImad Jbara is the COO of L2 Infinite Insurance and former COO of WoJo Media, where he helped transform client retention and scale revenues dramatically. He’s trained some of the largest sales teams in the world and worked alongside icons like Tony Robbins, Grant Cardone, and Alex Hormozi. Imad is known for building systems, empowering leaders, and creating the cultural foundations that allow companies to thrive.🔗 LinkedIn | WebsiteResources & Links MentionedProcess Street (SOP software)Maslow’s Hierarchy of NeedsImportant 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 Podcast Your Brand. Production and editing by Podcast Your Brand.

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.What does it take to scale a $100M company into a $365M powerhouse and beyond?In this episode, Cameron Herold sits down with longtime friend Erik Church, President & COO of 1-800-GOT-JUNK? and the O2E Brands portfolio. Together, they reflect on 30 years of leadership lessons, from fraternity houses and College Pro Painters to running one of the most recognized franchise brands in North America.Erik reveals how he uses the Painted Picture (now Vivid Vision) process to align his teams, why saying “no” is often the most important leadership move, and how 101 Life Goals have become a cultural cornerstone at O2E. He also shares the realities of working with a high-profile visionary founder, balancing bold, sometimes “crazy” ideas with operational discipline.If you’re a second-in-command navigating rapid growth, culture challenges, or a visionary CEO, this episode delivers actionable insights from one of the most seasoned COOs in the franchise world.Timestamped Highlights[00:01:00] – Erik’s journey from EF Education to leading 1-800-GOT-JUNK?[00:05:00] – How Painted Pictures (Vivid Vision) align teams across multiple brands[00:07:22] – Why great leadership is more about saying no than yes[00:09:19] – Lessons on culture from fraternity days, the military, and EF Education[00:13:41] – Navigating life as the COO “behind the brand” of a visionary founder[00:15:29] – Succession planning: why no one can advance until they replace themselves[00:19:19] – How Erik and Brian carve out alignment time and balance ideas vs. execution[00:21:00] – The power of 101 Life Goals in culture and recruitment[00:28:00] – Balancing big, bold founder ideas with scalability and replication[00:39:34] – Leading through constant change and technology transformation[00:42:19] – What Brian saw in Erik—and how their partnership works[00:46:22] – Erik’s biggest contribution to O2E Brands’ growthAbout the GuestErik Church is the President & COO of 1-800-GOT-JUNK? and the O2E Brands family (WOW 1 DAY PAINTING, You Move Me, Shack Shine). Since joining in 2011, he has helped scale the company from $100M to over $365M in revenue, focusing on culture, operational excellence, and leadership development. Previously, he served as President of EF Education Canada and held senior leadership roles across EF’s global businesses. Erik is also an avid outdoorsman, traveler, and motorcycle enthusiast.🔗 Website | LinkedInResources & MentionsRocket Fuel by Gino WickmanThe Dream Manager by Matthew KellyThe Wizard of Ads: Turning Words into Magic and Dreamers into Millionaires by Roy H. WilliamsImportant LinksConnect with Cameron:

In this episode of the Second in Command podcast, co-host Sivana Brewer is joined by Andrew Eisbrouch, COO of Abrams Media.During this fascinating conversation, Sivana and Andrew explore the unique journey of building and scaling businesses across multiple industries. You'll hear about the different challenges faced when moving from the early startup phase to a more mature stage of growth, and the lessons learned about balancing speed, creativity, and structure along the way. The discussion highlights both the excitement and complexity of operating in fast-changing environments where innovation and adaptability are key.The discussion also dives into team building, hiring strategies, and the cultural dynamics that shape organizations. From choosing between personality and experience when bringing people on board to the nuances of maintaining alignment in remote teams, Andrew offers valuable insights into leadership and people management. You'll learn the importance of trust, open communication, and knowing when to act.This episode offers a candid look at what it takes to grow not just companies, but also a vision for the future.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Andrew's journey from being a legal intern to a COO role in Dan Abrams' media businesses, including his decision to attend law school and his role in launching new businesses.The growth of the Law & Crime live trial network, starting with a legal-based website and expanding to live streaming murder trials.The acquisition of Law & Crime by Jellysmack, a European company focused on the creator economy.The challenges of transitioning from a COO role to a more visionary and risk-taking role. The need for a culture where mistakes are allowed and team members feel comfortable sharing ideas.And much more...Guest Bio:Andrew Eisbrouch is the former COO and General Counsel of Abrams Media and co-founder of Law&Crime, the viral true-crime network backed by Dan Abrams. He helped lead the business to a massive nine-figure acquisition while scaling the company’s production, social media, and legal operations. Now, he’s doubling down on his next venture: Bottle Raiders, which is rebranding to The Daily Pour on September 9th, a content and events brand at the intersection of liquor and non-alcoholic beverage media.Important Links:Connect 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 DelphiDisclaimer:The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not

In today's episode of the Second in Command podcast, Cameron explores one of the most common yet challenging aspects of leadership: how to handle conflict without falling into the role of constant mediator. You'll hear strategies for equipping managers to address issues themselves, drawing from structured frameworks that encourage ownership, accountability, and independent problem solving. Rather than leaders becoming the “referees” in every dispute, the discussion explores how to build confidence and skill within teams so they can work through disagreements productively.The conversation also dives into the practical realities of leadership training. It considers why teams often struggle to implement what they’ve learned, how to create space in busy schedules for professional development, and why ongoing practice is critical to mastery. By comparing leadership growth to athletic training, you'll discover the need for repetition, reflection, and reinforcement over time, and why one-time exposure isn’t enough for long-term results.Tired of playing referee? Learn how to build leaders who resolve conflicts and drive results on their own. If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The importance of growing skills and confidence through people rather than simply mediating conflicts. (0:37)Cameron's past experience with a leadership team at Blue Grace Logistics, and the importance of communication and praise. (3:31)Suggestions for implementing the Invest in Your Leaders training more effectively. (5:01)The adult learning cycle of abstract conceptualization, active experimentation, concrete experience, and reflective observation. (6:12)Why scheduling training time and holding team members accountable is vital. (7:58)And much more...Resources:Connect 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 DelphiDisclaimer:The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of The Second in Command podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at

In this episode of the Second in Command podcast, Cameron is joined by Nick Malone, former COO of Sitecore and a seasoned executive with over 24 years of leadership experience in the IT sector.During this fascinating conversation, Cameron and Nick explore the complexities of driving growth in a rapidly evolving industry. You'll hear how leaders navigate expansion strategies, balance ambitious goals with practical execution, and manage the challenges that come with building scalable systems. The discussion highlights how clarity of vision and disciplined prioritization become essential when a business is pushing toward the next stage of success.The discussion also looks at the human side of transformation. It examines how to guide teams through times of change, especially when uncertainty and cultural integration are at play. You'll gain insights into communication, alignment, and creating structures that help people feel supported while maintaining momentum.With practical takeaways and thoughtful reflections, this episode offers valuable guidance for leaders seeking to build resilience and long-term impact.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Nick's career journey, starting as an engineer and moving into sales and sales leadership, which allowed him to travel extensively.His experience living in Kazakhstan with his family, the cultural differences, and the need for a command-and-control approach in business.The transformation of Sitecore from an on-premise business to a SaaS offering, including the acquisition of modern technology companies.The importance of clear communication and vision in driving the transformation, as well as the role of talented individuals in making it successful.The role of the "cycle Sherpa" in integrating new employees, ensuring they are embedded into the business quickly and effectively.And much more...Guest Bio:Nick Malone is a seasoned executive with over 24 years of leadership experience in the Information Technology and Services sector, spanning the UK, Europe, the Middle East, the USA, Russia, and Central Asia. A graduate of Loughborough University in Manufacturing Engineering, he has built a rare leadership profile combining revenue growth, sales excellence, and operational efficiency. As former Chief Operating Officer of Sitecore, Nick led global operations, sales enablement, and large-scale transformation initiatives, consistently delivering results in both public companies and private equity portfolio firms. His expertise includes business development, cloud computing, and international partnerships, with a proven track record in driving growth across mature and emerging markets. Known as an agile leader and advocate for digital transformation, Nick is passionate about continuous learning, leadership development, and building high-performing global teams.Important Link:Connect 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: a...

Thinking about hiring a second in command? Getting it wrong can stall your growth, drain your energy, and wreck your culture. Getting it right can unlock scale, freedom, and balance.In this solo episode, Cameron Herold, founder of the COO Alliance and author of Second in Command, walks you through how to start the process of hiring a COO. He explains how to build a scorecard, define the role with precision, and identify the yin to your yang, so you can avoid a bad “marriage” and find the partner who actually complements your strengths.Cameron also shares why the CEO and COO should sit at the bottom of the org chart supporting their team, how to lean into your Vivid Vision to reverse-engineer the right fit, and why clarity on your weaknesses is the single most powerful step you can take before you hire.If you’re a CEO considering a second in command, this episode gives you a proven roadmap for making one of the most important hires of your career.Highlights[00:30] – Why great COOs are rarely “on the market” and where to actually find them[01:27] – The scorecard exercise that reveals exactly who you need[02:11] – How to spot the yin to your yang (and avoid culture clashes)[03:43] – Why you don’t have to be the cheerleader CEO if that’s not you[05:00] – Flipping the org chart upside down: why CEOs and COOs belong at the bottom[06:08] – Using your Vivid Vision to clarify the COO role before you hire[08:00] – Why “Who Not How” should guide your hiring decisions[09:32] – The mistake of trying to become good at what you suck at and what to do instead[12:12] – Why hiring a COO is more like marriage than recruitment[13:28] – Why most CEOs who ask Cameron to be their COO would be a terrible fitResources & MentionsWho Not How by Dan Sullivan & Dr. Ben HardyImportant 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.

In this episode of the Second in Command podcast, Cameron is joined by Andrew Rickett, Chief Operating Officer of Karmo, Australia’s largest car subscription provider.During this fascinating conversation, you'll hear how Andrew spent decades in a traditional industry before pivoting into a space that redefines consumer expectations. He shares insights on shifting customer demands, the evolution of long-standing models, and how Karmo is working to deliver more flexible, technology-driven solutions that better align with modern lifestyles.The discussion also explores how innovation and technology are shaping the way companies in this sector operate. From building a custom tech stack to integrating AI into the customer journey, you'll learn how efficiency, personalization, and self-service are becoming essential components of growth and differentiation.This episode covers everything from leadership, growth, and personal reflection to challenges such as recruiting top talent in a competitive market, strategies for building strong teams, and the importance of adaptability.Thinking about stepping into a COO role? Hear Andrew’s journey from CEO to COO and what it takes to thrive in both. If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The concept of vehicle subscriptions, and how they compare to traditional leasing and rental models.Andrew's post-acquisition transition from CEO of Motopool to the COO of Karmo, as well as the alignment of values and vision between them.The decision to keep both the Karmo and Motopool brands distinct due to different customer bases.The shift from making all decisions (as CEO) to managing specific areas of responsibility (as COO) and the importance of a supportive executive team.Karmo's focus on building a tech-enabled platform for an exceptional customer experience, and the potential for AI to enhance customer service.And much more...Guest Bio:Andrew Rickett is the Chief Operating Officer of Karmo, Australia’s largest car subscription provider, where he leverages his strong managerial background and extensive hands-on expertise to drive growth and innovation. With wide-ranging experience in business setup, implementation, and performance development, he brings a strategic vision that balances opportunity with risk while keeping customer and business needs at the forefront. A self-driven and self-reliant leader, Andrew is recognized for his advocacy, negotiation, and facilitation skills, consistently setting ambitious targets and leading by example. His focus on team building and leadership fosters an environment where people are engaged, motivated, and encouraged to excel, making him a key force behind Karmo’s continued success in redefining the automotive industry.Resources:Connect 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...

In today's episode of the Second in Command podcast, Cameron discusses one of the most critical hires a business can make, a role that directly impacts leadership alignment, financial clarity, and long-term success: the Chief Financial Officer or CFO.The conversation highlights how small red flags during the hiring process, such as scheduling mishaps or lack of accountability, can be early indicators of deeper issues that shouldn’t be ignored. You'll learn why asking tough, direct questions in interviews can uncover whether a candidate truly embodies the ownership and resilience needed for high-stakes leadership.Discover the relationship between this leadership role and the CEO, emphasizing the importance of trust, transparency, and mutual respect. Since not every CEO has the technical expertise to fully evaluate the position, Cameron shows how leaning on outside advisors or experienced professionals can provide the necessary insight to set clear expectations and define success from the outset. This ensures that both sides are aligned on responsibilities and performance measures.This episode offers practical guidance for any company seeking to strengthen its executive team and navigate the complexities of making the right leadership decision. Before you hire your next CFO, hear Cameron’s insider strategies for defining the role and setting clear expectations.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The nuances of hiring a CFO, including addressing red flags and setting clear expectations. The importance of outside experts like fractional CFOs or accounting firms in defining roles and setting new CFOs up for success. The role of outside experts in guiding a new CFO and ensuring they meet the company's needs.The value of having a fractional CFO participate in the interview process to assess the candidate's skills. And much more...Resources:Connect 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)Video call with Cameron: DelphiDisclaimer:The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of The Second in Command podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their...