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

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 fi...

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 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 leadershi...

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...

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 com...

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...

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 th...

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. R...

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 goa...

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 wit...

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 o...

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 indica...

In today's episode of the Second in Command podcast, co-host Sivana Brewer is joined by Sarah Harris, Fractional Chief Operating Officer at OMG Commerce. In this episode, you'll be taken behind the scenes of a dynamic leadership role that’s often misunderstood but critical to a company’s growth and health. Through candid stories and practical insights, the conversation explores the unique balance...

In today's episode of the Second in Command podcast, Cameron discusses a common misstep in leadership: blending strategy and planning into one concept.  While many leaders mistakenly see them as interchangeable, Cameron makes a compelling case for treating them as separate disciplines—each vital in its own right. Strategy is about creative thinking, exploring future possibilities, and setting...

In this episode of the Second in Command podcast, Cameron is joined by Roy Jain, the co-founder and Chief Operating Officer of Blue River Pet Care. In this fascinating conversation, you'll learn about building an organization that thrives on culture, leadership, and long-term vision. Cameron and Roy explore the foundations of creating a business during challenging times, the importance of surround...

In today's episode of the Second in Command podcast, Cameron explores what it truly means to have a second in command and why that role extends far beyond traditional job titles.  You'll hear how title inflation over the last few decades has blurred the lines between what it means to hold a C-level position and the actual responsibilities required for such a role. The discussion highlights th...

In this episode of the Second in Command podcast, Cameron is joined by Caitlyn Fagan, Chief Operating Officer for Inner Matrix Systems, a personal mastery training system for high achievers. During this fascinating conversation, Cameron and Caitlyn explore the unique challenges and opportunities of stepping into a leadership role that is not always in the spotlight but is essential for organizatio...

In today's episode of the Second in Command podcast, Cameron shares a powerful analogy between preparing for a trek through Nepal and leading a growing business.  Just like training for a demanding physical challenge, business leaders must begin with a broad vision, identifying where they want to go before diving into the finer details. Early momentum, even without a fully formed plan, sets t...

In today's episode of the Second in Command podcast, co-host Sivana Brewer is joined by Anthony Petitte, Chief Operating Officer at Finloc 2000 Inc. During this engaging conversation, Anthony shares candid insights about managing a fully remote team spread across diverse locations and cultures. The discussion explores the unique challenges of fostering connection and camaraderie when employees rar...

In today's episode of the Second in Command podcast, Cameron challenges conventional thinking about what it truly means to build a high-performing team. Rather than focusing on surface-level credentials or generic systems training, he dives deep into the often-overlooked soft skills that make or break leadership effectiveness—beginning with the critical, yet frequently neglected, art of interviewi...

In this special 500th episode of the Second in Command podcast, Cameron is joined by Meridith Kuba, Vice President of Operations and Sales for the COO Alliance. This time out, you're invited into a candid and energetic conversation that explores the unique dynamic between two long-time business collaborators. Through shared memories and deeply personal reflections, Cameron and Meridith peel back t...

In today's episode of the Second in Command podcast, Cameron explores the dynamic interplay between visionary entrepreneurs and the operational leaders who help bring their ideas to life.  The conversation centers on the constant flow of ideas that many CEOs generate and the need for a reliable system to evaluate, filter, and manage those ideas without derailing a company’s strategic directio...

In today's episode of the Second in Command podcast, Cameron is joined by Shanaz Hemmati, co-founder and COO of ZenBusiness. In this insightful conversation, Shanaz shares the behind-the-scenes story of building a modern company with a focus on simplifying a traditionally complex process. With a passion for technology and customer experience, she walks through how the organization evolved from a s...

In today's episode of the Second in Command podcast, Cameron shifts gears to discuss the meaning behind human connection and what truly matters beyond daily tasks and business pressures.  You'll hear the story behind a meaningful tattoo inspired by a quote about "walking each other home," emphasizing that despite life’s inevitable end, the real significance lies in caring for one another’s dr...

In today's episode of the Second in Command podcast, co-host Sivana Brewer is joined by Stephanie Meyer, RN, MS-FNP, NEA-BC, the Executive Vice President, Chief Nursing Executive, and Chief Operating Officer for Inpatient Operations at Children’s Mercy in Kansas City, Missouri. In this engaging and heartfelt episode, Sivana and Stephanie explore how our personal and professional lives are deeply i...