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In The TrenchesAuthor: Steve Divitkos
The only podcast dedicated exclusively to Entrepreneurs and CEOs running Small to Medium Sized Businesses (SMB). Nobody knows what its like to be an Entrepreneur or CEO unless youve been one. Though many understand the rewards of company leadership, very few understand the arduous journey thats required to get (and stay) there. I share my own lessons as an Entrepreneur and CEO, and interview experts spanning Sales, Leadership, Mental Health, M&A, and Operations (among others) all with a single goal: To improve the personal and professional lives of Entrepreneurs and CEOs running SMBs. Language: en Genres: Business, Entrepreneurship Contact email: Get it Feed URL: Get it iTunes ID: Get it Trailer: |
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Hiring Your Second in Command: With Cameron Herold, Founder of the COO Alliance and Former COO of 1-800-GOT-JUNK
Episode 7
Thursday, 16 April, 2026
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses * This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years*Click Here to Subscribe to the In The Trenches YouTube Channel*A “second-in-command” (sometimes a Chief of Staff, sometimes a Chief Operating Officer, and at other times a different title entirely) can be among a CEO’s more important and impactful hires. But, in my experience anyways, there is a lot that we don’t really understand about this hire: How do you know that you’re ready to hire one? What should they do and what should they not do? What title should we give them (and do titles even matter)? How much do we pay them and what forms of compensation are most appropriate? Should individual entrepreneurs consider hiring one as a sort of “proxy” for a business partner? To help me answer all of these questions (and a few more), I could think of no better guest than Cameron Herold. Among many other accolades, Cameron is the former COO of 1-800-GOT-JUNK (which he helped to grow from $2M to $106M in revenue during his 6 year tenure as COO), Founder of the COO Alliance (a peer network for “second in command” professionals, similar EO or YPO for Chief Executives), host of the “Second in Command” podcast, and author of a book of the same name. Based on all of these experiences, Cameron is now a highly sought after coach and speaker, particularly within the SMB community.
