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

Second in Command with Cameron Herold
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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 consultant, best-selling author, and speaker. He’s the mastermind behind hundreds of companies’ exponential growth and he’s touched thousands of businesses indirectly through his work.

  1. قبل ٤ أيام

    Ep. 523 - Brittany Dunn – Remarkable Resilience and Building Hope in 90 Days

    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...

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  2. قبل ٦ أيام

    Ep. 522 - Will Smith – How Trust and Time Created a Profitable 15-Store Brand

    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...

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  3. ٢٣ أكتوبر

    Ep.521 - Ebert Grobler – How “Grow People, Grow Profit” Built a Thriving Culture

    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 Collins About 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 | a href="https://www.rubydigital.co.za/"...

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  4. ٢١ أكتوبر

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

    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 | Linktree Resources & MentionsThe Speed of Trust by Stephen M.R. CoveyCrucial Conversations by Patterson, Grenny, McMillan & SwitzlerMeetings Suck by Cameron HeroldEmotional...

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  5. ١٦ أكتوبر

    Ep. 519 - FAN FAVORITE | Sarah Jones Simmer – 50 Million Users: The Ultimate Guide to Bumble’s Kind Leadership

    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 Guest Sarah 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 | Website Resources & MentionsSerena Williams x Bumble Super Bowl CampaignAdam Grant – Organizational Psychologist and AuthorKolbe Profile (KOLBE A)TEDWomen Conference Important 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 Note: 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.

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  6. ١٤ أكتوبر

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

    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 Course About 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 | Website Important 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

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  7. ٩ أكتوبر

    Ep.517- FAN FAVORITE | Harley Finkelstein – Inside the $100B Growth Strategy That Built Shopify

    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 | Website Resources & 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 essay Important 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 Note: 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....

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  8. ٧ أكتوبر

    Ep. 516 - Imad Jbara - The Shocking Mistakes COOs Make (and How to Avoid Them)

    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 | Website Resources & Links MentionedProcess Street (SOP software)Maslow’s Hierarchy of Needs Important 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 The 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.

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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 consultant, best-selling author, and speaker. He’s the mastermind behind hundreds of companies’ exponential growth and he’s touched thousands of businesses indirectly through his work.

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

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