COO Mastery: Cameron Herold Unveils the Secrets Behind | S2: E32 Executive Excellence
13 Nov 2025 · 17 min
Cameron Herold, former COO of 1-800-GOT-JUNK, grew the company from $2M to $106M in revenue and 3,100 employees. He breaks down what COOs actually do, why most companies get the role wrong, and the core skills that separate great operators from the rest.
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Cameron10 for 10% off (promo stated to run until September 30, 2024).
Grew revenue from $2 million to $106 million in about six and a half years; company headcount system-wide was just over 3,100 when he left.
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Welcome back everyone to another episode of Founder Story. I don't know if you know my story, but I was a COO for a long time and I felt like I should have had more development given to me because people are so focused only on CEOs. And that's why today I wanted to have Cameron Herold who I talked to maybe three, four years ago. We might have met 10 years ago at this point because he's been at this for a long time. He is called the CEO Whisperer. He's the founder of COO alliance and I love that he's so focused on coos. He's also the author of six game changing books such as Vivid Vision, the Second in Command and Invest in your Leaders. But Cameron, great to have you on the show.
Awesome. Daniel, good to see you. Thanks for having me.
I love that you're the second in command and you give the love to the coo. What inspired you to do this?
Well, I've been a second in command a couple of different times. Most notably, I was the COO for a company called 1-800-GOT Junk and I grew them from 2 million to 106 million in revenue in only six and a half years. We also went from. I was employee number 14 at the head office and when I left, we had just over 3,100 employees, system wide. So I'd scaled the company to, you know, pretty great size. We were the number two company in Canada to work for 330 cities, four countries. So in building something of that scale, that got me noticed. But it was also the fourth company that I built. So from there I just started writing books and realized that I knew the CEO audience. And as you mentioned, it really was very underserved. There were all these communities for CEOs or mastermind groups for CEOs. There was coaching for CEOs. But the reality is the CEO more often than not is not the person running the company. They're there controlling the vision and maybe strategy and the direction. But someone needs to be there on the day to day executing and making it happen. And so I decided to write the book on it. And I also have that organization called the CEO alliance, where we have members of companies that are all the second in command, whether it's CEO, President, vp, Ops, gm, whatever. But they're running these companies on behalf of their CEO and we've got a huge network of those people globally.
I think it's almost fair to say that the CEO could be one of the most important positions in any organization. Are there some sort of misconceptions that you're finding about this role? There's.
There's a couple of misconceptions, but to your point, yeah, I think it is. I would say it's the key role because it is the business marriage, right? It's the yin and yang to the CEO. Whereas every other functional head just has to be great at running their business area and pretty good at communicating with other teams. The COO needs to be able to understand all of the other business units. They need to be great at all the areas of the business that the CEO sucks at. They have to want to work on all the areas of the business that the CEO is drained of energy in. And that's a very different unique role it also has to match the stage of the company because if you're a very entrepreneurial organization, you need a CEO who's entrepreneurial. And then you also have to match the behavioral traits and the kind of idiosyncrasies of the CEO because you really are their marriage spouse, much more than, you know, any of the aunts and uncles have to be to the husband or wife. It's really that husband and wife relationship. So that's the first key. It really is, probably is, and I talk a lot about it in my book. The second command, the misunderstood component, is how do you find them? When do you need one? What title should we put on them? I see so many companies putting the wrong title on really good people and they end up overinflating the values the person thinks they have and what metrics they should be measured by and even what they feel like they should be paid just because they've been given a big title. And they start comparing against other titles.
I'm such a big proponent of putting people in the right places based on their strengths or hear the right title for the right position. This can be huge and can be a detriment. I feel like with many organizations when you do the opposite.
Well, yeah. And you know, in the last 20 years, we've had a lot of title inflation. Twenty years ago, to get a C level title, whether you're chief marketing officer, chief financial officer, chief technology officer, chief operating officer, you had to be a pretty major player at a major company. And in the late 90s, the banks started giving out VP titles to everybody. So everybody we knew had a VP title, even though they were pretty junior at a bank. And it became to be a marketing tactic like a brand, like a way to open doors. So we started giving away bigger titles. When the Internet boom started to happen from the late 90s through to 2008, we started giving away equity in lieu of compensation and titles to become part of the marketing package. And that really is where some of the sloppiness started.
I can't help but laugh because I can think back to my corporate days and they were just like giving out titles like they wouldn't even give you a raise. It's like, here, have this new title. Makes you feel really good. We will return to our show shortly. But first, let's talk about today's sponsor. Magnesium Breakthrough by Bio Optimizers. Did you know 4 out of 5Americans don't get enough magnesium? Crucial for over 300 biochemical reactions in your body. Here are signs of magnesium Deficiency, irritability, anxiety, insomnia, muscle cramps, high blood pressure and even constipation. I know I suffer from a few of these, but many supplements don't work well because they use low quality magnesium. That's why Magnesium Breakthrough by Bio Optimizers is recommended. Offering seven forms of absorbable magnesium, Bio Optimizer stands by their products with a 365 day money back guarantee. That's insane. So make sure you visit bioptimizers.com B I O O P T I M I Z R S.com Dan Robbins that's bio optimizers.com D A N R O B B I N S for a special offer. And make sure you use the code founders f o u n d e r s founders and you get your 10% off. So check out bioptimizers.com to learn more. And back to the show.
Now they could afford to and they could afford to give their money away. But if you're a company of, you know, 25 to 200 employees, you can't be giving money away to people just for the sake of some big marketing title that they've got. You gotta be a little more cautious.
So I know you have your course Invest in youn Leaders and you talk about 12 core leadership skills. What are one or two that you think everyone needs to know right now?
The reality is everyone who's managing people needs to be very strong at something called situational leadership. And most people have had no exposure, let alone training or certification in that skill. They need to be good at coaching adults because they're really coaching direct reports on a day to day. And they have to be trained and certified in delegation, let alone stuff like project management or time management or handling conflict or running interviews or running meetings. But I think those are the three core skills. Situational leadership, coaching and delegation.
Why do you think so many people in the startup realm, so many founders have a big issue with delegation?
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Really been trained in it. So the first part is they don't know how to do it properly so they feel like it's just easier for them to do it for themselves. But a leader's core job is to grow people, right? Our result, our job is to get results through others. So we need to delegate more and then spend more time growing the people's skills and confidence and connections so that they can do more of what needs to be done inside of the business. What happens is the leaders tend to freeze because they don't have the skills at training people, they don't have the skills at coaching people, they don't have the skills at managing projects, they don't have any skills at handling the communication that goes with it. So because of that, it's just easier for them to do it themselves and they slow down their own growth of their organization. It also happens with mid level managers, right? Let alone the entrepreneur being bad at it. Most managers that are managing teams and people have never been actually given the proper training to scale up their organization until they get into a big company with, you know, probably 500 plus employees where they have a real training department in place. Most organizations don't have that though.
I can think back to companies at work where there was 50,000 employees and I'm not sure if the leaders I had were trained either. So I think this is a big issue from small companies to big companies. So I appreciate that you're, you're helping and these are core skills. Everyone needs to know. If there's a CEO out there that is thinking like, okay, I'm going to start this company, but I need a CEO, what should they look for?
The first thing they should do is not look for someone else. They should look at themselves and really understand their strengths, their weaknesses, what feeds them with energy and what drains them of energy. What parts of the business are they just so great at and they love working on and then start to figure out what that other person might look like who's taking all that other stuff off their plate. So it's really understanding yourself. Second thing is almost as if you were going to write an operating manual to yourself as the entrepreneur or CEO. If you were going to write a two page manual to you, what are your personal core values? How do you operate on a day to day basis? How do you like to be communicated with? How do you like people to come to you with problems? How do you like to be, you know, included in discussions? What don't you want to be included in? And really, if you understand yourself, you can clearly articulate that message of what you're looking for as that yin and yang second in command who's coming in to match you.
Do you think that maybe some people, when they're fine, they want to be the CEO just because they are the founder of the company, I'm the CEO. But maybe they'd be better as the CEO. Are you finding this?
Not. Not really. Most CEOs have a DNA that is just very different from the operational CEO or that operational second in command. Most entrepreneurs are out to prove something. They have a vision. The nice thing is they can delegate everything except genius. What you will find is some CEOs who are very inward facing CEOs they might be very product focused, very tech stack focused, very kind of operationally focused. And they need a very outward facing CEO or so or coo. An example of this would be Harley Finkelstein from Shopify who's a very outward facing second in command. Business development, sales, marketing, pr, public markets, talking to salespeople. Like a real kind of outward facing culture, revenue driving second in command. And Tobias Luque, the CEO happens to be a very inward focused operations, execution, you know, technology, engineering. So much less of the outward facing, revenue driving. And again that's what's different about this role is you have to be good at whatever the CEO sucks at. But you don't find too many CEOs wanting to give up, you know, vision and culture and strategy.
Yeah. I was going to ask you if there's someone out there who is more vocal, who is the CEO, which I didn't even know he was the CEO. I thought he was the CEO of Shopify. So thank you for.
And that's because we see him so much in that outward facing role. Here's a great example. When I was the second in command for 1-800-got junk, I was very similar to Harley at Shopify, but the current CEO at 1-800-got junk. Do you know who that who is? What his name is?
Is it Brian?
No, Brian's the CEO. But his current COO has been in the role now for 13 years and no one could know know his name because he's a very in. Eric Church, I've known him for 37 years. Doesn't talk to the press, doesn't talk on stages. Right. He only focuses on strategy and people and execution. Even though he's matching the same CEO. But the season that that company is in, they needed a very different style COO than the season that they were in when I was there.
I think that's very inspirational and I hope that other people, the second in command People will start to become more public facing. I think it inspires people because it's like everyone wants to be the CEO, but that is not our fit, you know, like not everyone is fit to be that. So I think this gives people the inspiration to say, you know what? And on top of that you have this incredible community. So can you tell me more about your community that you're cultivating or you've been cultivating?
Yeah, we've been cultivating now for about seven years. We have members from 18 countries. 80% of our members second in commands are from the U.S. 10% are Canada. The other 10% are split over 16 countries. You need at least 5 million or greater in revenue to qualify. So the average size company is around 30 million. Our biggest O is around 300 million. And it's all around members connecting with each other to grow their skills, their confidence and their connections. It's really not me teaching them how to be a COO because a lot of them are way more qualified than I've ever been. It's them collaborating with each other, sharing resources with each other, showing up for monthly speakers, talking to each other in between events over the Slack group, and then coming together in person a couple times a year to really build those deep connections and get to know each other more.
I think some of the most important things happen from these connections, from networking with the right people. I think we're so, we're so engulfed in our work and what we're doing that we don't always take the time to go meet new people, nor do we even know where to meet them. Right. So I think it's great what you're doing and I'm sure a lot of people are being positively impacted. So if other people want to re. They want to get your books, they want to be a part of the alliance, they want to learn more about your course and leadership skills. How can they do so, yeah, the.
Leadership skills they should all go and check out. It's called investinyourleaders.com it has the 12 core skills there. If your listeners want, I'll give a promo code that they can use. If they, they use Cameron 10, that'll get them 10% off the invest in your leaders course. That code will probably end in a few months, but let's say that It'll run until September 30th of 2024. Anybody listening? After that, there's still going to be tons of value. You just won't get the 10% off.
Well, Cameron, thank you so much. It's so great to talk to you again. Even though it's been like three or four years since we spoke. Always amazing. You never know who you're going to meet again in life. That's the thing I've definitely always try to live by. But thank you so much for joining us today on Founders Story.
Appreciate it, Daniel. Thanks for having me.
Thank you for tuning in to Founders Story. Keep exploring, keep dreaming and join us next time for more inspiring entrepreneurial journeys.
We all take good care of the things that matter. Our homes, our pets, our cars. Are you doing the same for your brain? Acting early to protect brain health may help reduce the risk of dementia from conditions like Alzheimer's disease. Studies Studies have found that up to 45% of dementia cases may be prevented or delayed. By managing risk factors, you can change make brain health a priority. Ask your doctor about your risk factors and for a cognitive assessment. Learn more@brainhealthmatters.com the holidays mean more travel.
More shopping, more time online and more personal info in more places that could expose you more to identity theft. But LifeLock monitors millions of data points per second. If your identity is stolen, our US based restoration specialists will fix it, guaranteed or your money back. Don't face drained accounts, fraudulent loans or financial losses alone. Get more holiday fun and less Holiday worry with LifeLock. Save up to 40% your first year. Visit LifeLock.com SpecialOffer terms apply.