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

In today's episode of the Second in Command podcast, Cameron explores creative and impactful ways to enhance team communication and alignment during planning sessions and retreats. You'll discover an engaging, visual icebreaker that encourages self-reflection and team bonding, revealing personal insights and shared aspirations. From there, the conversation shifts to a powerful feedback exercise designed to foster transparency and personal growth within leadership teams.Cameron offers insights into strategic goal-setting and execution. You'll hear about a structured process for translating big-picture objectives into actionable projects, emphasizing the importance of prioritization and cross-departmental collaboration.Through a blend of proven exercises and real-world examples, this episode will provide you with the tools to foster more effective leadership and create a clearer path toward organizational success.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!In This Episode You'll Learn:A fun and engaging exercise that uses visuals instead of words to help team members share personal insights, strengthen connections, and align on goals for an event or planning session.  A proven approach for defining company-wide objectives, ensuring that key projects are aligned with long-term success while avoiding common pitfalls like overcommitment.  How different business areas can work together to refine and commit to core projects, preventing bottlenecks and maximizing efficiency.  The challenges leaders face in managing competing priorities and how the ability to say no — or not yet — can be the key to long-term organizational success.And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron’s latest book "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, co-host Sivana Brewer is joined by John Wallet, President of STC Safety and Risk Management.This conversation explores the complexities of leading teams and navigating the often delicate balance between visionary and integrator roles. Sivana and John discuss the importance of cultivating confidence in decision-making and the value of having systems in place to support clear communication, particularly when facing moments of uncertainty. You'll gain insights into learning from mistakes and how to move forward, shedding light on how leaders can grow and adapt while maintaining focus on their organization's objectives.You'll discover the challenges and rewards of working with a younger workforce, emphasizing the need for empowerment and accountability. John reflects on the generational differences in priorities, particularly around culture and values, offering advice on fostering an environment where employees feel supported and truly part of the company's mission.This episode offers practical advice, a look into the intricacies of leadership roles, and a behind-the-scenes glimpse into balancing career with family life.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:John's role at STC Safety and Risk Management, specializing in safety and risk management consulting for the construction industry.The role of visionary leaders in guiding a company towards technological adoption and innovation.The concept of an integrator in EOS (Entrepreneurial Operating System), which aligns with John's natural strengths in data-driven, logical thinking.The importance of having clear processes and standard operating procedures (SOPs) to ensure consistency and accountability. The importance of a healthy relationship between the visionary and the integrator.And much more...Resources:Connect with John: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron explores the dynamic partnership between two key leadership roles within a company: the CEO and the COO. Cameron discusses the often underappreciated relationship that drives an organization’s success, highlighting the distinct yet complementary functions that each leader provides. You'll gain insights into the fine balance between visionary leadership and operational execution, and the importance of a strong, trusting relationship between these figures.Learn the significance of alignment between the strategic and tactical elements of a business. Cameron discusses how the right leadership pairing can propel an organization forward, but also touches on the challenges that come with maintaining that synergy. In addition, he explores the importance of delegation, growth, and communication within the leadership team to avoid burnout and foster sustainable success.This episode offers a look at how effective leadership teams plan for the future and stay aligned, ensuring that all members are on the same page to achieve long-term goals.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:Why clear roles, responsibilities, and communication between the CEO and COO is essential. (1:00)How meddling in the COO's responsibilities by the CEO can damage trust and productivity. (3:42)Why the CEO should be responsible for good news, allowing the COO to handle tough decisions. (6:54)The purpose of skip level meetings and their potential impact on organizational advancement. (13:14)The importance of delegating tasks to grow people and align the organization. (18:09)And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, co-host Sivana Brewer is joined by Filip Keuppens, Executive Vice President of The Pickle Juice Company.During the conversation, Sivana and Filip dive deep into the complexities of leadership and the balancing act of managing day-to-day operations while simultaneously planning for the long-term success of an organization. You'll discover the importance of building genuine relationships with team members, focusing on transparency and trust. These principles are essential when navigating the challenges of team dynamics, particularly in times of growth and change.Hear about the challenges of working within a rapidly changing business landscape. Filip shares his personal experiences of moving from tactical execution to high-level strategy, discussing the need to adapt and lead from the front in a constantly evolving environment. There's a strong emphasis on maintaining a hands-on approach, even at the highest levels, to stay grounded and connected with the team’s day-to-day challenges.Whether it’s coaching a sports team or learning a new skill, you'll learn how personal endeavors can complement professional goals and contribute to personal growth.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 challenge of educating consumers that The Pickle Juice Company's product is not made from actual pickles, especially in the US market.Filip's evolution from building the sales and marketing infrastructure to becoming the third partner and eventually the Executive Vice President.The importance of hiring for culture rather than experience, and promoting from within whenever possible.The challenges of balancing working 'in' the business and working 'on' the business, and the need to stay focused on long-term sustainability. Why you should treat the next title or job as the starting line, not the finish line.And much more...Resources:Connect with Filip: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

The host shares a personal journey, highlighting how attention deficit disorder (ADD) shaped his path in education and business. He reframes ADD as a potential superpower rather than a flaw, emphasizing the unique strengths it can bring to entrepreneurship. Discussing strategies for success, he focuses on leveraging short bursts of intense focus and the importance of prioritization and delegation. Empowering those with ADD, the conversation encourages embracing one's unique traits to flourish in the workplace and beyond.

In today's episode of the Second in Command podcast, Cameron is joined by Susan Heinking, Senior Vice President of High Performance and Sustainable Construction at Pepper Construction.During this fascinating conversation, you'll be taken behind the scenes of a dynamic leadership journey where the balance between structure and creativity plays a pivotal role. Susan shares insights into navigating growth within a well-established framework while maintaining the foundational values that shaped the organization. With candid reflections, the conversation highlights how intentional communication and adaptability remain central to leading a high-functioning, purpose-driven team.Hear about the art of managing complexity without losing touch with the work that ignites passion. Thoughtful leadership practices, including strategic delegation and fostering a culture of self-awareness, underscore the importance of empowering teams to evolve while staying aligned with larger goals. You'll learn how tools for collaboration and team dynamics are being reimagined to meet today’s ever-shifting challenges.From embracing failure as a teacher to incorporating surprising reminders to stay lighthearted amidst pressure, this episode is rich with takeaways for anyone striving to lead with intention, empathy, and a little bit of fun. 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 evolution of sustainability from energy efficiency to resilience and human health.Susan's approach to presenting sustainability as a cost-effective solution to clients.Her experience working in a male-dominated industry and the empowerment of seeing more women in leadership roles.The importance of keeping employees informed and engaged with new information and technologies.The role of managing company-wide initiatives and ensuring they are on track and on time. And much more...Resources:Connect with Susan: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron discusses the complexities of building and optimizing a high-performing team while navigating the challenges of growth, leadership transitions, and strategic decision-making. You'll discover the importance of identifying key roles, leveraging technology, and ensuring that each team member brings measurable value. A candid exploration of industry pitfalls reveals the common struggles leaders face when dealing with unreliable service providers, ineffective hires, and the need for clear accountability. Throughout, the emphasis remains on cutting through the noise to build a strong, results-driven organization.  You'll also get a behind-the-scenes look at an innovative hiring process that flips traditional recruitment on its head. Instead of relying on resumes and standard interviews, this approach puts candidates to the test with real-world assignments that showcase their skills, efficiency, and ability to think critically. A standout example demonstrates how one individual not only met expectations but exceeded them by incorporating AI-driven insights and delivering a polished, comprehensive strategy.This episode is a reminder that, despite the weight of decisions and the complexity of business operations, the real goal is to enjoy the process.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!In This Episode You'll Learn:Why hiring project managers as a "release valve" instead of training account managers to be self-sufficient is a flawed strategy.The importance of having a leadership team that can implement and maintain systems and processes.The value of celebrating people who notice inefficient systems and encouraging them to speak up.Cameron's personal analogy about the pain of getting divorced to illustrate the importance of moving on quickly.And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron’s latest book "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, co-host Sivana Brewer is joined by Andrew Alexandrovich, Chief Operating Officer of Environmental Incentives.During the conversation, Sivana and Andrew explore the complexities of navigating company growth and the unique challenges that arise when an organization scales rapidly. They explore the intricate balance between quality and quantity, particularly in a professional services environment, and discuss the difficulties that leadership teams face in maintaining high standards while managing a fast-paced, evolving business.You'll gain insights on the strategic processes employed by the EI executive team to prioritize and manage competing demands. Andrew reflects on the practical steps taken to ensure smooth collaboration, both internally and externally, while emphasizing the value of regular check-ins and clear agendas.This episode also offers lessons Andrew has learned about balancing careful planning with adaptability and the need for continuous learning. 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 at Environmental Incentives, starting as one of three employees and growing to becoming the COO in 2020.The importance of maintaining a people-focused culture, with a focus on learning, adaptability, and continual improvement.The challenges of scaling systems from a small business to a mid-sized business operating globally. EI's strategic planning process, including a five-year strategy and annual strategy. The tactical steps taken to ensure executive team cohesion, including regular check-ins with clear agendas.And much more...Resources:Connect with Andrew: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron dives into the unique dynamics between COOs and CEOs, comparing them to how men and women perceive the world differently. Cameron discusses the relatively short tenure of most COOs and how the role evolves as a company scales. He also touches on how the COO’s skill set may not always keep pace with the company’s growth, leading to frequent turnover.You'll learn about the changing gender dynamics within the COO position, noting how women now comprise a significant portion of COOs. With examples from well-known companies like Facebook, Cameron delves into the idea that the COO role is often misunderstood as a stepping stone to the CEO position, when in reality, many COOs don’t aspire to take on that higher-level responsibility.This episode offers insights into the evolving responsibilities of COOs in today’s business landscape, particularly their role in digital transformation and technological adaptation.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!In This Episode You'll Learn:Why the role of a COO is often more dynamic and requires a broader set of skills compared to other functional heads. (2:19)The significant decrease in the gender gap in COO roles over the past 15 to 20 years. (2:44)Why compensation for a COO should be tied to strategic insight, P&L responsibility, and the number of partners brought into the company. (7:12)The role of the COO in project alignment and resource allocation (8:11)And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron is joined by COO Alliance Member Tony Skowron, COO of The Beyond Collection, a commission-free marketplace connecting meeting planners and luxury hospitality partners.During the conversation, Tony shares a compelling journey marked by growth, challenge, and intentionality. From navigating the complexities of entering an established but evolving team, to building trust and driving alignment, Tony reflects on the importance of listening first, learning deeply, and leading with clarity. The discussion touches on how transitions can be both delicate and powerful, especially when stepping into a high-stakes leadership role within a tight-knit organization.The conversation evolves into a powerful exploration of what it means to develop people—not just for the sake of productivity, but to elevate culture and long-term impact. You'll hear the story of how a bold leadership initiative was launched, which weaves together personal conviction and professional strategy, all within the backdrop of an industry that often overlooks these deeper developmental needs.This episode is a must-listen for anyone curious about what it takes to lead with purpose, align teams around vision, and grow leaders from the inside out.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 ensuring the quality of planners, as they must meet specific criteria to be included in the Beyond Collection platform.Tony's experience with the Ritz Carlton Leadership Academy and his interest in leadership training and white glove service. The Beyond Collection's leadership training program, which aims to invest in the development of leaders within the hospitality industry. Tony's previous role as a COO and VP, the challenges of growing a company, and the importance of aligning values and vision.And much more...Resources:Connect with Tony: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders