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

• Ep. 531 - Watters International Realty COO Aldo Siciliano Shares How EOS Drives Remarkable Calm in Rapid Growth

  In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Aldo Siciliano, COO and President of Watters International Realty, a fast-scaling residential brokerage serving multiple Texas markets.Aldo shares how Watters uses EOS (Entrepreneurial Operating System) to create alignment, simplify decision-making, and support a fast-moving, marketing-driven business. He breaks down the real work of being an integrator, why adaptability matters more than expertise, and how to keep a visionary’s ideas grounded in reality without killing momentum.They dig into hiring proven talent vs. emerging talent, managing burnout and stress in relationship-heavy industries, and knowing when a new tool is genuinely helpful versus just shiny. Aldo also talks about maintaining simplicity at scale, building systems that teams will actually use, and why emotional management is one of the hardest parts of leading in real estate.This is a practical, honest, detail-rich episode for any COO navigating growth, complexity, and a CEO with a strong visionary engine.Timestamped Highlights[00:00] – What EOS really is and why it works for small to mid-size companies[01:08] – Introducing Aldo: data-driven operator, people-first leader[02:51] – Watters International Realty: multi-market residential brokerage across Texas[03:52] – Aldo’s journey from VP of Marketing to COO & President[05:17] – Why being a generalist (not a specialist) made him a stronger COO[07:16] – What made Aldo want to work with CEO Chris, a “zero-to-one” visionary[08:54] – How the CEO–COO decision-making dynamic works in real life[10:08] – Why Aldo was chosen for the COO role: integration mindset + complement to the visionary[10:33] – Why Watters implemented EOS and how it fit their bandwidth[11:54] – The core pieces of EOS that actually move the needle[13:36] – Small changes vs. big changes and why incremental improvements matter[16:48] – SOPs, knowledge bases, and keeping documentation simple[18:24] – Why Aldo uses Motion instead of Asana/ClickUp[20:58] – The hidden cost of complex tools and the myth of “software will fix everything”[22:56] – Lessons from failed system implementations and the danger of poor adoption[24:29] – “Teach people how to think, not what to do” and how Aldo applies this[28:09] – Coaching teams through burnout, stress, and emotional fatigue[29:42] – The emotional load on sales leaders: “You’re in the attitude management business”[31:25] – Why burnout often comes from the wrong people in the wrong seats[33:01] – The importance of hiring experienced talent during scaling[38:40] – Proven talent vs. emerging talent in fast-growth companies[40:17] – The risk of a wrong sales leader: attrition, client loss, culture loss[41:47] – Why individual impact shrinks as companies scale[42:56] – Aldo’s next big initiative: new expansion strategy[43:40] – Where to find Aldo onlineResources & Mentions• EOS – Entrepreneurial Operating System• Motion (project + time management)• monday.com• Salesforce• Asana• ClickUpAbout the GuestAldo Siciliano is the COO and President of Watters International Realty, a multi-market Texas-based residential brokerage. Known for his blend of analytical thinking and empathetic...

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• Ep. 530 - MAPS COO Steven Huang on Why Leaders Everywhere Are Turning to Psychedelics Now

  In this episode, Cameron sits down with Steven Huang, the Director of Finance, People, IT, and Community at MAPS, the Multidisciplinary Association for Psychedelic Studies. Steven helps lead global efforts to bring psychedelic research, policy reform, and public understanding into the mainstream, building on MAPS’ 40-year history at the forefront of mental health innovation.Steven shares his unlikely path from life insurance actuary to Silicon Valley analyst to psychedelic industry operator, including how psychedelics shaped his career decisions, his leadership growth, and his move into the second-in-command role during a major organizational crisis. He and Cameron explore what the government is getting right, where the psychedelic movement is headed, and how MAPS balances scientific rigor with visionary cultural work.If you’ve been watching psychedelics move from taboo to the TED stage to boardrooms and leadership circles, this conversation gives a rare inside look at the movement from someone steering the ship.Timestamped Highlights00:00 Steven opens with a core leadership lesson around self-belief.01:28 Cameron introduces Steven and MAPS’ mission.03:00 Cameron’s first encounter with Rick Doblin and the psychedelic space.04:09 What MAPS is and how it’s shaped the psychedelic movement.05:18 How cannabis legalization opened the door for psychedelic conversations.07:23 Steven on public stigma shifting and psychedelics entering mainstream business culture.09:00 Understanding MDMA therapy, ketamine, and where research is now.11:41 Cameron’s personal experiences with psychedelic therapy.12:44 How government perception and bipartisan interest are evolving.14:45 How MAPS is funded and why conferences aren’t profit centers.15:39 The path from MAPS to Lycos and Resilient Pharmaceuticals.18:00 Real-world use: psilocybin dispensaries and psychedelic churches.20:19 Where psychedelics help… and where clinical caution still matters.22:20 The role of intention in therapeutic and recreational use.24:32 Steven’s psychedelic-inspired career pivot from actuary to Facebook.27:21 Cameron’s first MDMA experience and how it changed his worldview.29:05 When company culture goes too far.30:30 The challenge of leading a nonprofit in a regulated landscape.33:16 The FDA setback and massive internal shift at MAPS.37:04 Steven’s first encounter with Rick Doblin and the reality of working with a visionary founder.39:00 Steven’s advice to his younger self.Resources & MentionsMDMA-assisted therapyKetamine therapyPsilocybinAyahuascaPsychedelic Science ConferenceResilient Pharmaceuticals (formerly Lykos Therapeutics)Rick DoblinAbout the GuestSteven Huang is the Director of Finance, People, IT, and Community at MAPS, the Multidisciplinary Association for Psychedelic Studies. With a background spanning actuarial science, Facebook’s people analytics team, and diversity leadership roles across Silicon Valley, Steven brings a rare mix of analytical rigor and human-centered...

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• Ep. 529 - FAN FAVORITE | Zendesk COO Tom Keiser Shares The Powerful Execution Rhythm That Transformed Zendesk

  We’re bringing this episode back because listeners couldn’t get enough the first time around. Cameron sits down with Tom Keiser, COO of Zendesk, to unpack how he helped scale the SaaS powerhouse to a billion-dollar trajectory. Tom shares how he bridged the gap between IT and operations, built cadence-driven execution rhythms, and created visibility across the business while keeping the culture humble, fast, and customer-obsessed.If you’re leading a growing company and need a blueprint for scaling without suffocating the entrepreneurial edge… this one hits hard.Timestamped Highlights01:11 Meet Tom Keiser and his path from CIO to COO02:00 Early days: Capgemini, E&Y, and stepping into tech leadership05:27 What Zendesk actually does (and how it scaled globally)07:33 How SaaS changed the business–IT power dynamic08:55 Why CIOs must become business partners, not tech overseers10:54 The PMO strategy that keeps Zendesk aligned as it scales12:04 Tom’s weekly operational cadence pulled from retail13:50 Turning insights into action: Sales, pipeline, and global adjustments15:37 How Zendesk avoids bureaucracy while growing fast17:39 Culture: The Danish “Humbled It” mindset19:36 Saying no without killing momentum20:57 Managing customer support when your whole business is CX23:38 Omnichannel done right: Continuous conversations, not disconnected pings26:14 Machine learning inside Zendesk Guide29:18 How Tom balances immediate execution with long-term scaling32:55 What smaller companies can learn from Zendesk’s growth34:34 Vulnerability and learning to step into discomfort as a leader36:25 When to trust your team and when to drop into details37:51 How Zendesk’s founder transitioned out of day-to-day execution39:18 Market risks, public cloud, open-source, and economic uncertainty39:46 What 5G will unleash for future customer experiences43:12 Building whole leaders, not siloed operators44:13 Tom’s advice to his 21-year-old selfAbout the GuestTom Keiser is the Chief Operating Officer of Zendesk, where he oversees global operations, IT, enterprise analytics, security, and go-to-market execution for one of the world’s leading customer experience platforms. With 25+ years of experience across retail, technology, and SaaS, Tom blends deep technical expertise with business-led operational leadership. Before Zendesk, he served as CIO at L Brands and spent years in management consulting at Capgemini and Ernst & Young.🔗 LinkedIn Resources & MentionsCapgemini / Ernst & YoungZendeskImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance - The World’s Leading Community for Seconds in CommandGet Cameron’s book: Second in Command: Unleash the Power of Your COO BookTake Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)Chat or video call with AI Cameron via

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• Ep. 528 - Land O’Lakes COO Brett Bruggeman on Driving Success in a $16B, 104-Year Cooperative

  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...

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• Ep. 527 - TrueNorth Companies COO Matthew Rathje Shares Why Purpose-Fueled Strategies Drive Sustainable Growth

  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,...

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