Episode Overview

Podcast: Second in Command: The Chief Behind the Chief with Cameron Herold
Episode: 505 - The Unvarnished Truth About Being the Number Two Leader
Host: Cameron Herold
Date: August 28, 2025

In this solo episode, Cameron Herold explores what it truly means to be a second in command, cutting through title inflation and misconceptions about the COO and similar roles. Drawing from personal experience and industry observations, Cameron provides practical advice on identifying, hiring, and working with the right second-in-command for your organization. The episode is particularly candid about the nuances that define executive roles, the importance of self-awareness for leaders, and the dynamic partnership between a CEO and their key operational partner.

Key Discussion Points and Insights

1. Defining the "Second in Command"

• More than a COO:
  • The “second in command” role isn’t limited to the COO title. It can be a VP of Operations, Director of Operations, GM, Operations Manager, or even an Executive Assistant.
  • It ultimately describes the “yin and yang partner” for the CEO, unique to each organization.
  • (00:01) "Your second in command could be a COO, could be a Vice President, operations, it could be a Director of Operations, could be an Operations Manager, could be a GM, could be an Executive Assistant. It's your yin and yang partner." — Cameron Herold

2. Title Inflation: The COO Title in Perspective

• History of Title Inflation:

  • Title inflation accelerated in the late 1990s, as organizations—especially banks—used VP titles as marketing tools for relatively junior roles.
  • The dot-com era increased this trend, with inflated titles and equity offered in lieu of traditional compensation.
  • (00:28) "To have a true C-level title, you had to be a major player at a major company... then the banks in the late 90s started to give away titles of VP to people as a marketing tool... title inflation started." — Cameron Herold

• What Makes a True COO:

  • Requires strategic insight, autonomy, P&L (Profit & Loss) responsibility, authority to bring in people, and compensation aligned with the role.
  • Under-compensated “COOs” are often simply Directors or Managers in disguise.
  • (02:40) "If you have $120,000 person, they're not a COO, they're a director. A true COO is in the 250 to 550 range. I was getting paid $312,000 18 years ago." — Cameron Herold

3. The Importance of Fit: Stages of Company Growth

• Matching Skill Sets to Company Phase

  • Cameron shares his own experience at 1-800-GOT-JUNK, emphasizing that being the right COO depends on the company’s season of growth.
  • Early-stage growth requires one type of leader, while later-stage scaling calls for others with different backgrounds or expertise (e.g., franchising, corporate structure).
  • (04:35) "I was the right COO for Brian from 2 million to 100 million. It was the right stage... The current COO, Eric Church, has been there for 12 years... He's been incredible from the 100 million to the billion. It's absolutely his zone of genius." — Cameron Herold

• Individual Fit Over Generic Experience:

  • COOs are often much more context-specific than other executives (e.g., Marketing or IT), making hiring for this position uniquely challenging.
  • (06:10) "If you're the head of marketing for a finance firm, you could probably be the head of marketing for all finance firms... If you're the COO for a fitness company, you may not be the right fit for that CEO." — Cameron Herold

4. The Dynamic Between CEO and COO

• The “Inevitably Frustrating” Relationship:
  • Every COO, regardless of skill, will eventually “drive you crazy” as a CEO—and vice versa. The secret is continual growth, coaching, and partnership, not expecting a problem-free relationship.
  • (07:15) "If you replace them with somebody else, that new person is going to drive you crazy too... Our job as a leader is to grow people... delegate everything except genius." — Cameron Herold

5. Building the Ideal Second in Command

Self-Awareness Comes First

• Entrepreneurs should start by assessing their own strengths, weaknesses, and the tasks that drain them vs. energize them.
• Build a job description based on the “flip side” of your own limitations and energy drains.
• (08:15) "Do an activity inventory of all the stuff that you suck at as an entrepreneur... flip it upside down and that becomes what this new person is going to be doing." — Cameron Herold

Match Skills and Personality

• Use personality assessments (e.g., Kolbe, DISC) to define what kind of person will mesh with you.
• Document the specific roles, responsibilities, accountability metrics, and compensation before beginning the search.

Compensation and Title Alignment

• Avoid inflating titles or underpaying key roles. Ensure the title matches responsibility and compensation.

Sourcing Talent

• Strong endorsement of using specialized executive search firms, especially culture-focused ones, to poach top operators.
• Use your company’s vivid vision as a tool—share your ambitious roadmap with top candidates and filter for those who resonate with where you’re headed.
• (09:45) "I like getting executive search firms to poach really good people and then giving them the vivid vision. And if the really good people don't like the vivid vision of where we're going, I still want to keep searching for the people that do." — Cameron Herold

Notable Quotes & Memorable Moments

• On Title Inflation:
  (00:52) "Remember when you had, like, your 25-year-old friend was the Vice President of some random bank? You're like, what the fuck? He's like, no, I'm 12 layers below the CEO." — Cameron Herold

• On Fit for the Stage:
  (04:54) "Eric's been there for 12 years. He would have been a horrible COO completely... He didn't have the entrepreneurial skills. He wasn't from the franchising space. But he's been incredible from the 100 million to the billion." — Cameron Herold

• On the Challenge of the COO Role:
  (06:12) "It's a really tough role to hire for... I would be a horrible COO for 95 to 98% of their companies because I don't match the skill set of the industry." — Cameron Herold

• On People Problems:
  (07:45) "Marcelo [Claret] asked me, 'When are people not going to be the problem anymore?' I'm like, 'You're the 82nd largest company in the United States. They're always the fucking problem.'" — Cameron Herold

• On Building the Right Partnership:
  (08:19) "Describe the kind of person you are as a leader... Look for the counterpart to that, someone who matches really well with that personality profile." — Cameron Herold

Timestamps for Key Segments

• 00:01: Definition of “second in command”; role is more than just COO
• 00:28: History and effects of title inflation in business
• 02:40: What constitutes a true COO — skills & compensation
• 04:35: Cameron’s history at 1-800-GOT-JUNK and the importance of fit by company stage
• 06:10: Why COO roles are uniquely challenging to fill
• 07:15: Real talk: COOs/second in commands will always challenge the CEO; leadership is about developing people
• 08:15: Starting your COO search: self-awareness and reverse engineering your weaknesses
• 09:45: How to find great candidates — use executive search, poach talent, and leverage vivid vision

Conclusion and Actionable Takeaways

• The second in command is a highly individualized, context-sensitive role—don’t get distracted by titles.
• Understand your needs by first being brutally honest about your strengths, weaknesses, and what drains you as a leader.
• Match the person to the company’s stage and your own leadership style using assessments and thorough job design.
• Invest in proper compensation and don’t conflate title with ability or organizational impact.
• Leverage specialized executive search and a compelling company vision to attract the right operational partner.

This episode is a must-listen for CEOs, founders, and anyone looking to understand the real requirements and best practices for hiring— and retaining— a second-in-command.