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PODCAST

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

Second in Command 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 entrepreneurship

All Episodes

42:31

Ep. 525 - FAN FAVORITE | Anna Collins – Inside...

Second in Command: The Chief Behind the Chief with... ·

2025/11/06

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

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50:36

Ep. 524 - Daniel Quinonez – Leading Change in a...

Second in Command: The Chief Behind the Chief with... ·

2025/11/04

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

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50:18

Ep. 523 - Brittany Dunn – Remarkable Resilience and...

Second in Command: The Chief Behind the Chief with... ·

2025/10/30

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

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47:02

Ep. 522 - Will Smith – How Trust and Time Created a...

Second in Command: The Chief Behind the Chief with... ·

2025/10/28

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

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37:52

Ep.521 - Ebert Grobler – How “Grow People, Grow...

Second in Command: The Chief Behind the Chief with... ·

2025/10/23

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

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52:13

Ep. 520 - Cory Raggi – How to Stay Grounded and Lead...

Second in Command: The Chief Behind the Chief with... ·

2025/10/21

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

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48:40

Ep. 519 - FAN FAVORITE | Sarah Jones Simmer – 50...

Second in Command: The Chief Behind the Chief with... ·

2025/10/16

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

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44:11

Ep. 518 - Brent Hagan – How to Lead Through Feedback,...

Second in Command: The Chief Behind the Chief with... ·

2025/10/14

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,

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46:10

Ep.517- FAN FAVORITE | Harley Finkelstein – Inside...

Second in Command: The Chief Behind the Chief with... ·

2025/10/09

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

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32:08

Ep. 516 - Imad Jbara - The Shocking Mistakes COOs...

Second in Command: The Chief Behind the Chief with... ·

2025/10/07

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

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48:15

Ep. 515 - FAN FAVORITE - Erik Church – How To Scale A...

Second in Command: The Chief Behind the Chief with... ·

2025/10/02

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

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47:32

Ep. 514 - Andrew Eisbrouch - Scaling Secrets Fortune...

Second in Command: The Chief Behind the Chief with... ·

2025/09/30

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

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09:03

Ep. 513 - Elevating Leadership: Conflict Resolution &...

Second in Command: The Chief Behind the Chief with... ·

2025/09/25

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

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46:37

Ep. 512 - Nick Malone - Crushing It Worldwide Using...

Second in Command: The Chief Behind the Chief with... ·

2025/09/23

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

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16:08

Ep. 511 - How to Hire the Right COO Without Making a...

Second in Command: The Chief Behind the Chief with... ·

2025/09/18

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

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45:16

Ep. 510 - Andrew Rickett-The COO Powering a New Era...

Second in Command: The Chief Behind the Chief with... ·

2025/09/16

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

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08:52

Ep. 509 - Unlock CFO Success Secrets No One Tells You...

Second in Command: The Chief Behind the Chief with... ·

2025/09/11

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

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53:05

Ep. 508 - Sarah Harris - Uncovering the Secrets of...

Second in Command: The Chief Behind the Chief with... ·

2025/09/09

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 required to lead both strategically and operationally, juggling long-term vision with short-term

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09:44

Ep. 507 - Think Ahead Act Now: Winning the Game with...

Second in Command: The Chief Behind the Chief with... ·

2025/09/04

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 direction, while planning deals with the tangible steps needed to execute that vision within a tightly focused

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45:35

Ep. 506 - Roy Jain - How Top CEOs Hack Culture to...

Second in Command: The Chief Behind the Chief with... ·

2025/09/02

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 surrounding yourself with trusted partners, and the mindset required to navigate uncertainty while pursuing

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526 results

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