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

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. Production and editing by Podcast Your Brand.

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: 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, 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 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 your own risk.

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 your own risk.

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: 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 your own risk.

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 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 your own risk.