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

In today's episode of the Second in Command podcast, Cameron explores the question of whether businesses truly need a Chief Operating Officer or if alternative solutions would be more cost-effective and practical.Many business leaders assume they need a high-level executive to manage operations, but taking that step prematurely can lead to unnecessary costs, friction, and even structural upheaval. Before committing to a major hire, it’s essential to assess the true gaps in the business—because sometimes, the best solution isn’t a full-time executive at all.  You'll learn why a well-placed assistant or a specialized department head might resolve bottlenecks without the financial and organizational burden of a second-in-command. Even when higher-level coordination is required, alternative options — such as bringing in an experienced leader on a part-time or project basis — can provide flexibility while maintaining control over costs and responsibilities.  This episode shows the reasons why, before making a major commitment, leaders must evaluate whether they’re solving the right problem — and whether there’s a smarter, more scalable way forward.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 a COO too soon can be a costly mistake — and what to consider before making the commitment.  When a functional department head, such as a CFO or VP of Technology, might be a better fit than a COO.  The benefits of hiring a Fractional COO as a flexible, cost-effective alternative for scaling operations.  How to assess whether a COO will truly add value to your business and align with long-term goals.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

Roy Heldshtein, Managing Partner and COO of Team8, shares his expertise in navigating leadership complexities in the fast-paced tech world. He discusses the vibrant entrepreneurial spirit of Tel Aviv and the synergy between finance and operations. Roy emphasizes effective team management and the importance of structured communication. His unique approach to meetings highlights prioritization and the value of one-on-ones for decision-making. He also reflects on the transformative potential of AI and the significance of cultural integration through shared experiences.

Paul Bryson, Managing Director of Virtuzone and expert in UAE business landscape, shares invaluable leadership insights. He discusses the importance of adaptability and humility in leadership, emphasizing personal growth through learning from diverse experiences. Paul also explores the complexities of starting a business in the UAE, highlighting regulatory environments and corporate tax benefits. Additionally, he dives into fostering a high-performance culture and the power of emotional intelligence in team management. A treasure trove of practical advice for current and aspiring leaders!

In this engaging conversation, Mike Wisner, COO of Mawer Capital LLC, offers a wealth of wisdom on building influence in a fast-paced world. He discusses the importance of adaptability and leveraging networks for growth. Mike reveals the challenges of maintaining team balance amid advances in AI and the significance of strategic storytelling in celebrity marketing. He also touches on how their Legacy Makers Program helps entrepreneurs share their narratives effectively. Packed with relatable anecdotes, this talk is a goldmine for aspiring leaders!

Discover the transformative power of recognizing team achievements in leadership. Explore how meaningful acknowledgment can boost morale and foster growth, often surpassing traditional monetary incentives. Delve into the complexities of performance bonuses and learn why they can sometimes demotivate rather than inspire. Gain insights on structuring effective reward systems that truly motivate top performers while maintaining fairness, and discover practical tips to align recognition with core values.

Spencer Matthews, COO of Stemregen and managing partner at Fifth Hammer, shares insights from his journey in the health sector. He discusses the innovative plant-based stem cell enhancers Stemregen is developing, offering a natural alternative to traditional therapies. The conversation dives into leadership dynamics, emphasizing the need for curiosity and adaptability when navigating new roles. Spencer highlights effective communication strategies for remote teams and the delicate balance of executing tasks versus empowering others, all while fostering collaboration and trust in high-performing teams.

Brad Stevens, Founder and CEO of Outsource Access, dives into the art of balancing operational growth with employee satisfaction. He reveals how integrating global talent, especially from the Philippines, enhances efficiency while maintaining a strong local culture. Brad dispels common outsourcing myths and highlights the importance of clear communication and thorough onboarding processes. By crafting career pathways for virtual assistants and utilizing advanced tools, he shows how to navigate the challenges of outsourcing, driving both innovation and employee retention.

During the conversation, Cameron and Milly dive into the intricate balance of leadership, strategy, and adaptability required to navigate the fast-evolving landscape of modern business. You'll find a fresh perspective on how dynamic roles can bring order to chaos while preserving the creative spark essential for growth. Through candid insights, Milly shares her approach to designing flexible yet effective systems that allow companies to flourish during critical early stages.They also explore the delicate interplay between innovation and structure in growing organizations. How much is too much when it comes to planning? How do leaders strike a balance between guiding their teams and fostering autonomy?Milly also reflects on her unique career path, revealing how unconventional choices shaped their ability to lead and problem-solve. With a focus on people, purpose, and long-term sustainability, she shares how her experiences in philosophy, communication, and creative thinking helped build a foundation for success.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:Milly's role at the London School of Economics and Imperial College London, focusing on entrepreneurship and commercializing IP. (3:11)The importance of finding something that is both a strength and a passion to productize. (5:39)The balance between offering cost-effective solutions and delivering value to clients. (16:28)How Milly matches clients with the right fractional COOs based on experience and personality. (19:24)And much more...Resources:Connect with Milly: 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 is joined by Max Hansen, CEO for Y Scouts, a purpose-based executive search firm. The discussion centers on the unique approach and philosophy of a retained executive search firm, exploring how their process differs from traditional contingent search models. You'll discover a distinctive approach that incorporates aligning leadership with organizational culture, emphasizing purpose and values as key drivers in recruitment. Cameron and Max detail a covert discovery process that prioritizes building genuine connections with candidates before revealing company names or roles, fostering trust and deeper insights into alignment and fit.You'll also gain insights into the client-recruiter relationship and the challenges companies face when managing their own hiring processes in conjunction with outside search firms. Advice centers on ensuring collaboration through clear communication, transparent processes, and structured planning—emphasizing that over-interviewing without strategy can lead to inefficiencies. This conversation shows that successful recruitment relies on balance: combining established interviewing methods with strategic executive search insights while maintaining candidate engagement and experience throughout the hiring journey.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 difference between contingent and retained search firms, including the thorough due diligence and market mapping done by retained firms. (0:43)The three unique elements of Y Scouts: aligning people with culture and values, role visioning, and a leadership model for hiring. (5:12)The importance of understanding a firm's process, how they find candidates, and their track record. (8:57)The need for collaboration and a scoring mechanism to ensure consistency in evaluating candidates. (14:56)And much more...Resources:Connect with Max: 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 is joined by Christopher Ager, Chief Commercial Officer for Taskrabbit, an online marketplace that matches freelance labor with local demand, allowing people to find help with tasks.During the conversation, Cameron and Christopher explore the unique challenges and decisions involved in leading a growing company within a dynamic industry. Christopher reflects on his journey, highlighting how prioritization and a deep understanding of customer needs shape effective leadership.You'll learn the importance of adaptability in leadership, particularly in terms of working remotely and managing a diverse team. Gain insights into navigating team dynamics, balancing personal and professional commitments, and ensuring alignment on goals and expectations.Throughout this episode, you'll discover thoughtful advice for those at the start of their careers, emphasizing the value of focusing on work that sparks personal interest and collaboration with inspiring colleagues.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:How spending time understanding his team and operations during his first 90 days at Taskrabbit helped Christopher make informed, confident decisions. (12:50)The importance of aligning short-term actions with long-term goals and working closely with the CEO to ensure that the company is setting itself up for future success. (16:40)How Christopher utilized his early days in the company to focus on building strong, effective relationships with his leadership team and understanding the deeper issues in the business. (20:40)How he tailors his one-on-one approach based on individual team members' needs, focusing on their progress toward long-term goals and addressing roadblocks. (39:00)…And much more!Resources:Connect with Christopher: 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