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

Latest Episodes:

Ep. 471 - The Growth Engine: Fueling Teams and Talent May 01, 2025

Show notes

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...

Important Links

Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership 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

Ep. 470 - Environmental Incentives COO, Andrew Alexandrovich Apr 29, 2025

Show notes

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...

Important Links:

Connect with Andrew: Website | LinkedIn
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership 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

Ep. 469 - Navigating the COO Landscape: Leadership in a Changing World Apr 24, 2025

Show notes

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...

Important Links

Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership 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

Ep. 468 - The Beyond Collection COO, Tony Skowron Apr 22, 2025

Show notes

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...

Important Links:

Connect with Tony: Website | LinkedIn
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership 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

Ep. 467 - Timely Triumphs in Team Dynamics Apr 17, 2025

Show notes

In today's episode of the Second in Command podcast, Cameron reveals a fresh approach to team building and annual planning that goes beyond stale meeting rooms and rigid agendas.

You'll discover a game-changing strategy that combines the camaraderie of cooking, the serenity of nature, and the power of collaborative goal-setting. Learn how swapping hotel conference rooms for an Airbnb retreat can transform your leadership team’s dynamic, fostering deeper connections through shared experiences. You'll also find out how timing and intentional preparation can set your organization up for a strong year ahead.

Through real-life success stories, actionable insights, and frameworks like EOS, this conversation dives into the importance of vivid vision, setting clear three-year goals, and crafting actionable one-year plans. From establishing quarterly accountability to aligning staffing and budgeting with long-term objectives, this episode equips leaders with practical steps to energize their teams and maximize results.

Whether you're planning your next annual retreat or seeking innovative ways to strengthen your organization, this discussion is your roadmap to 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:

How simple activities like grocery shopping and cooking together can strengthen team bonds, create a family-like dynamic, and elevate your annual planning retreats. (1:04)
Why hosting your planning sessions in an Airbnb instead of a hotel can foster creativity, relaxation, and stronger connections among team members, setting the stage for more effective collaboration. (2:58)
The critical deadlines for locking in goals, budgets, and staffing plans to ensure a smooth transition into the new year. (5:06)
How quarterly planning sessions can align your team’s priorities, leverage frameworks like EOS, and establish accountability with clear goals and review processes for every business area. (8:21)
And much more...

Important Links

Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership 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

Ep. 466 - Neat Strategy and Operations Lead, Alicia Ramirez-Ingalls Apr 15, 2025

Show notes

In today's episode of the Second in Command podcast, co-host Sivana Brewer is joined by Alicia Ramirez-Ingalls, Strategy and Operations Lead at Neat, a video communications device design company based in Oslo, Norway.

Throughout the conversation, Sivana and Alicia explore the challenges and experiences of navigating high-pressure environments, particularly when self-doubt and imposter syndrome inevitably arise. Alicia shares insights on how to balance personal uncertainty with the need to contribute meaningfully in demanding professional settings.

You'll hear about the concept of a "fail fast" mindset, which involves embracing failure as part of the learning process. Alicia explains how speed, agility, and a willingness to iterate can lead to breakthroughs, with real-world examples illustrating how this approach has shaped decision-making and growth within the company.

This episode offers practical advice for those looking to build effective partnerships in any field.

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:

Alicia's strong relationship with Janine Pelosi, the CEO of Neat, and her decision to join Neat after a career break.
The importance of not shying away from new challenges and making the most of opportunities to learn and grow.
Why leaders should provide a safe space for team members to communicate and learn from their mistakes.
The importance of trusting oneself and the team and being willing to take on new challenges.
And much more...

Important Links:

Connect with Alicia: Website | LinkedIn
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership 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

Ep. 465 - STS Capital Partners Chairman and Founder, Rob Follows Apr 10, 2025

Show notes

In today's episode of the Second in Command podcast, Cameron is joined by Rob Follows, Chairman and Founder of STS Capital Partners.

During the conversation, Rob and Cameron discuss the intricacies of selling businesses and navigating the complex world of mergers and acquisitions. They explore the challenges faced by entrepreneurs and business owners when it comes to maximizing the value of their companies and understanding the true impact of strategic advice.

You'll discover the often-overlooked factors that can influence the final deal, including the role of private equity firms and traditional investment banks, and why these entities may not always align with the goals of family-owned or entrepreneurial businesses. Rob also emphasizes the importance of being strategic, cautious, and well-prepared throughout the process.

From climbing the world’s tallest peaks to speaking about life planning and business value maximization, this episode provides both practical business advice and inspiring life lessons for entrepreneurs aiming for greatness.

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 maximizing value when selling a business, especially for strategic buyers.
How the 'Rembrandts in the attic' analogy explains the hidden value that strategic buyers see in a company.
The challenges of working with smaller companies and the need for a certain level of business maturity.
Common misconceptions about the mergers and acquisitions (M&A) process and the importance of aligning interests.
The need for entrepreneurs to have a clear understanding of their required and preferred outcomes.
And much more...

Important Links:

Connect with Rob: Website | LinkedIn
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership 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

Ep. 464 - aiOla COO, Alon Peleg Apr 08, 2025

Show notes

In today's episode of the Second in Command podcast, Cameron is joined by Alon Peleg, a seasoned Israeli leader and COO of aiOla, a cutting-edge conversational AI lab.

During the conversation, Cameron and Alon explore the strategic decisions behind building a high-performance company culture and scaling effectively within a competitive industry. Alon shares insights on creating an environment that empowers employees to thrive while aligning with a larger vision, emphasizing the importance of hiring the right talent, especially in leadership and technical roles.

You'll gain insights into navigating the complex and often lengthy process of selling to large enterprises. Alon highlights the key tactics for successfully penetrating these organizations, including understanding internal processes, building strong relationships, and focusing on continuous engagement. Hear about the importance of establishing champions within the customer base, ensuring that product evaluations are not taken lightly, and handling the delicate balance of pushing for growth while staying true to the company's focus.

This episode offers advice about being bold, embracing risks, and continuously challenging oneself in both career and life, adding a final layer of inspiration to the broader themes of growth, resilience, and the pursuit of new horizons.

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 the voice will be the main user interface in the future, as well as aiOla's ability to provide accurate and quick conversational capabilities.
How aiOla's digital forms can replace paper-based processes, capturing data more efficiently and accurately.
The value of understanding the customer's processes and the need for a champion within the customer organization to facilitate adoption.
Alon's experience in hiring a new management team, including a CTO and a director of marketing, to scale the company.
And much more...

Important Links:

Connect with Alon: Website | LinkedIn
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership 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

Ep. 463 - The Art of Transition: Guiding Growth Through Empowered Teams Apr 03, 2025

Show notes

In today's episode of the Second in Command podcast, Cameron discusses the intricate journey of transitioning from a hands-on business operator to a strategic owner.

Discover the mindset and practical steps required for a CEO to step back from daily operations without losing the essence of their leadership. You'll learn the importance of clear communication, robust planning, and maintaining alignment within the team.

Cameron offers actionable strategies for empowering a leadership team, including mentorship programs, setting up peer learning networks, and refining systems to inspect outcomes without micromanaging. He emphasizes the balance between delegation and abdication, ensuring the CEO retains strategic oversight while allowing the team to grow and succeed autonomously.

Whether you’re a business leader looking to step back or an entrepreneur building sustainable systems, this episode provides a wealth of ideas to shape a thriving, self-reliant organization.

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:

How to prepare your team and organization for a long-term leadership transition, including leveraging strategic planning frameworks like EOS. (16:37)
The importance of crafting a vivid vision to ensure continuity and alignment during and after a leadership shift. (19:02)
Strategies to empower your leadership team through mentoring programs, peer learning networks, and structured support systems. (21:45)
The difference between effective delegation and abdication, and how to inspect outcomes without micromanaging your team. (23:10)
And much more...

Important Links

Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership 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

Ep. 462 - The Lifestyle Investor COO, Ryan Casey Apr 01, 2025

Show notes

In today's episode of The Second in Command podcast, Cameron is joined by Ryan Casey, Chief Operating Officer for The Lifestyle Investor.

Ryan shares insights from an unexpected career journey that began in a surprising industry and led to expertise in sales, systems, and personal development. The conversation explores the power of structured approaches to relationship-building, professional growth, and leadership, highlighting how early experiences shaped a mindset focused on efficiency and strategic thinking.

You'll learn about Ryan's pivotal career transitions, from managing multiple businesses to stepping into a leadership role within a rapidly growing organization. The conversation explores the challenges of scaling a founder-driven company, striking a balance between maintaining core values and building systems that allow for sustainable expansion.

Whether you're an entrepreneur, a sales professional, or someone looking to optimize your approach to success, this episode is packed with thought-provoking lessons and actionable strategies.

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:

Ryan's experience with Orangetheory, including the challenges of marketing and generating leads during the COVID-19 pandemic.
The benefits of having a founder-led company and the challenges of transitioning from a passion project to a business.
The various asset classes the Lifestyle Investor covers, including private equity, credit funds, real estate, etc.
Ryan's approach to marketing and learning, including joining coaching programs and masterminds to stay ahead of industry trends.
And much more...

Important Links: