Many founders wait too long to hire their #2—or worse, they hire the wrong one. In this session, a Collective 54 member shares two radically different outcomes from hiring a COO. The first was a costly misfire that added complexity and stalled growth. The second unlocked scale, freed the founder’s time, and put the firm on track to double its run rate. This session is a candid look at how to make this pivotal hire—and what happens when you get it wrong.
What you’ll get from this session:
• The hidden risks of hiring a COO before you’re ready—or without the right criteria
• Lessons from a failed search: red flags missed, questions not asked
• The decision framework that led to a successful second hire
• How to onboard and empower a COO to create immediate leverage
• What changed when the founder stopped being the bottleneck
Why it matters:
• A misaligned COO hire costs more than money—it drains time, morale, and client trust
• Getting the right #2 is the difference between working in the weeds and leading at altitude
• A founder’s ability to scale often depends on one decision: who’s helping you run the firm
TRANSCRIPT
Greg Alexander: Hey everybody, this is Greg Alexander. You’re listening to the ProServ Podcast, brought to you by Collective 54. If you’re new to this show, this show is dedicated to founders of boutique professional services firms. And we aim to help you do 3 things: make more money, make scaling easier, and make an exit achievable. On this show, we’re gonna talk about the critical role of the number 2. Sometimes that’s called a chief operating officer. Some of you use EOS, and you call that an integrator. Some of you call it a president, whatever you call it, it’s the right-hand person to the founder that, when you’re scaling a boutique pro serve firm, is a mission-critical hire. And we’re gonna talk about that. And we have a long-standing, well-respected member with us, Lori Turner-Wilson. And Lori has quite the story. She’s been at this for a while. She has a COO, it’s working fabulously for her. She had a little bit of a journey to get there, and we’re gonna learn about that journey, and she’s got some great lessons for us. So, Lori, for those that might not know who you are, could you please introduce yourself to the audience?
Lori Turner-Wilson: Yeah, absolutely. Greg, glad to be here. Thanks for the invite. So, I am the CEO and founder of Red Rover Sales and Marketing Strategy. We’re a national B2B marketing agency, and what distinguishes us is we guarantee our outcomes for clients. I started as an entrepreneur at the age of 13. I actually formed my own business then. It was a dog show, of all things. We made a tidy profit. I knew I was meant to be an entrepreneur, even from that young age. After college, I went into enterprise marketing in the Fortune 1000 space, and I had the opportunity in those roles to hire some of the top 10 largest ad agencies and marketing firms in this country. They were wildly creative and innovative, but they were equally uninterested in moving the needle on metrics that actually matter, such as incremental gross profit. It finally dawned on me, after dragging them into peak performance for years, that I should build what I couldn’t find, and Red Rover was born in 2006 as a result.
Greg Alexander: Great story. Thank you for that. Okay, so let’s jump into it. What was the moment that you realized that you needed a number 2? Like, what triggered you?
Lori Turner-Wilson: Well, we’re an EOS traction company, and so I appreciate the principle of visionary and integrator, and I had worn both of those hats for the entire length of the agency. We were hitting the ceiling — which is a traction principle. Growth… we just could only scale up to a certain point because my time was fractured between both roles, and I knew that in order to scale to the degree that I know is possible with this agency, I needed to have a strong number two. So I made that call, brought in a recruiting firm, and started the search.
Greg Alexander: Okay, very good. Now, I’m hoping that your story is going to inspire some of our members, because I know all of them pretty much at this point. And there’s several of them that need a number 2 and don’t have one. When I ask them why, they give me 3 things, and I want to hit you with these 3 things and get your reaction. So first is cost. They fear that it’s very expensive to hire a fantastic person. Costs a lot of money in salary and bonus, but also sometimes these folks want equity, and they’re worried about that. The second thing is risk. If they hire the wrong person, it’s very disruptive. It could cause employees or clients to be unhappy. And third, which is probably the biggest one, is ambiguity — what does a COO do in a boutique, and how is that different from what the founder does? So if you wouldn’t mind, let’s just take those one at a time. Let’s talk about the first one: cost. How did you get your head around making the investment?
Lori Turner-Wilson: Yeah, I mean, it’s a big investment, but when I see now what having the right integrator in place can do, it’s not a big investment at all. In fact, I should have done it 5 years ago. The amount of leverage you can get when you are in your distinct visionary seat — with the mindshare and mental capacity to be creative and innovative, and really begin to imagine what’s possible for the future — is remarkable. My integrator’s been on staff for 5 months. We are doubling our run rate in 5 months. Yes, it is an investment, and it’s a bigger investment when you make the wrong hire, and I’ve certainly done that once in this role. I’ve seen the contrast between good fit and poor fit, and I knew going through that experience exactly what I needed and didn’t need in this second hire. It’s an absolute game changer. I think every ProServe firm, when they get to a certain size, is going to need to hire an integrator. It’s the best decision I made.
Greg Alexander: Fantastic. Okay, let’s go to number two: risk. You mentioned that it took you a couple times to hire the right person. So the risk of making a mistake — you actually felt the first time around. Help members overcome their fear.
Lori Turner-Wilson: Yeah, the mistake I made was not trusting my gut through the interview process. Even when I brought this individual on, you always, as a founder, want to give someone the benefit of the doubt. It took me 9 months to ultimately make a change in that role, but in reality, by the second week, I knew it. Down deep, I knew it. Through the interview process, the things that I did differently in the second round — and this is how you reduce your risk — it needs to be a really thorough vetting process. You need scenarios, simulations, testing, and cognitive tests. It’s worth being slow to hire that position, but you can’t wait to start that process. The upside compared to the risk is tremendous. Just make sure that you’re thorough with the interview process, and it’ll work out in the end.
Greg Alexander: Now, sometimes when people have that experience, they say, okay, I agree, I need an integrator, I’m gonna hire a number 2. They do it, and it doesn’t work out, so they’re unwilling to give it another try. They try some alternatives — for example, they might rent a fractional COO, or like you mentioned, EOS has a whole implementer program where you can rent a certified EOS implementer. There are other ways to do this that are more part-time and therefore might reduce risk. Did you consider any of those? And ultimately, you didn’t choose one — how come?
Lori Turner-Wilson: Yeah, I actually used a fractional integrator to help me find my second integrator. I knew that I didn’t go through the interview process properly the first time to make sure the individual was a fit for me — not just in skill set, but in whether they were wired to operate in a boutique pro serve firm. He came out of big agencies — very large ones — and it’s just, you know, Greg, a whole different animal in our world. So I wanted someone on the outside who could be a second set of eyes. This fractional integrator interviewed my top candidates, reviewed interview recordings, helped me refine the interview guide, and brought objectivity I might not have had. He happens to be a Collective 54 member as well. That’s how I de-risked it. But for me, I believed I needed someone who knew my agency inside and out — someone in it 40 hours a week, living and breathing my agency. My business has complexity that really required a full-time insider. I don’t think that’s the right move for every ProServe firm, but it was for me.
Greg Alexander: Yeah, very good. You’re right. Everything is situational. I’ve gotten to know you a bit and understand what your business does.
Greg Alexander: And I can see why the type of work you do, and the clients you serve, full-time is probably the right solution for you, but everybody needs to ask themselves that question, you know, is that the right thing? I do want to highlight something that you did that not a lot of our members are doing, but might be the unlock that we just revealed, and that is Lori used a certified EOS implementer, but to find a full-time integrator. That’s a unique application of that resource. Sometimes people use that implementer just to outsource the implementation of EOS, but finding a full-time person, that’s a very interesting approach, so I appreciate you sharing that with us. All right, let’s go to the third one. So this issue of ambiguity, which is, you know, what are the roles and responsibilities? How do we separate the visionary and the integrator? Again, that is a little nuanced, based on what your firm does and the personalities involved. How did you figure out, you know, what you were going to do versus what your number 2 was gonna do?
Lori Turner-Wilson: You know, going into the first time I made that hire, I didn’t define that very well. It was sort of back of the napkin. But going into it the second time, after learning everything that I learned the first time, that fractional integrator I brought in, we worked together, and we defined visionary role, integrator role, with a fair amount of specificity, defined those, where there would be overlap, where there wouldn’t be overlap at the end of the day, and ultimately devised the interview guide to really map to that pretty clearly. So, I knew that on the, you know, on the visionary side, that I would, at least for the next year or two, develop the scalable sales team for the organization, but the complete operation would shift to the integrator. And so, my integrator, Jen, is every client deliverable, account management, finance, legal, technology, shared services, all of that rolls directly into her, and I don’t have to think about it. Unless there’s a big issue that she wants to collaborate on, I trust her. She’s making good decisions, she understands and is aligned with the vision. It’s really just phenomenal, the speed of growth that we’ve seen in this five months.
Greg Alexander: Yeah. You know, I can feel your energy. You are re-energized and more passionate than normal, and you’re a pretty passionate person. Tell me what your life looks like now, now that you have this great number 2 on your hip.
Lori Turner-Wilson: Well, and you have to really understand and contrast what it looked like, and when you and I had a conversation at about the 6-month mark for that prior integrator, you probably didn’t see the same person. I was tired. I didn’t enjoy my job anymore. I’ve enjoyed this work since the age of 13 when I started marketing, and all of a sudden, I didn’t enjoy it more, and it wasn’t my former COO’s fault, he just wasn’t wired for the role, and we didn’t have chemistry. And now that I’ve found someone, we are in perfect sync, we are aligned, we challenge each other, but we see that vision together very clearly. I love what I do more than I ever have in my entire life. I am out there focused on authority marketing and building awareness in our market and educating CEOs about what they from a marketing performance standpoint. I don’t dread the day. I look forward to the day. This is why we become entrepreneurs. And if I had done this 5 years ago, I mean, I’m just… that’s where I’m kicking myself. The mistake was not making this decision faster.
Greg Alexander: Yeah. Well, we all have to go through this. So just in my journey with Collective 54, which is my third company. It took me 3 times to get the right integrator in place, so… and and I’m someone who at least claims to know what he’s doing. And it took me 3 times to get it right. I mean, people decisions, they’re hard decisions, but I echo what you say. I mean, my integrator is Jeff Klaumann, who’s the president of Collective 54, and I love what I do, because he does all the things that I’m not good at. He loves those things, and he’s good at them, so it’s like peanut butter and jelly, right? It’s a great combination. All right, let me… let’s conclude with one more question, and that is, if you’re a member of Collective 54 and you’re listening to this. And you do not have a number 2, or you’ve tried this before and it hasn’t worked. What, what advice would you give that person?
Lori Turner-Wilson: Well, either way, I think I’d get some external help. So, I would bring someone in that can see your blind spots, that can assess the kind of integrator that’s going to work best with you, someone who has seen integrators across a variety of pro-serve firms, so that you’re just… you’re… the learning process is so much expedited as a result. So, I think you lean in. You have to do it. This is the way that you scale, but if you have the right advisors on board. I had multiple external advisors looking at these candidates, watching the game film, my recordings of interviews, to make sure that they were identifying any blind spots I missed. I wasn’t that thorough the first time, that’s on me, but you can learn from the mistakes that I made and do it right the first time.
Greg Alexander: Yep. Great advice. I would like to add to that, if I can, and that is, I’m often quoted as saying, and this is an accurate quote these days with AI, you don’t know what’s authentic or what isn’t. This is accurate. Scaling a firm is too much work for one person. So a founder needs a partner, and that partner is a chief operating officer. And, when that happens, the founder, the visionary, is allowed to be the visionary. And there’s nobody who makes a bigger impact on a firm than a visionary. I mean, Lori’s business is rockin’ right now. Why? Because she’s in her role of visionary, and that’s what’s causing the rocking to happen. So I want to inspire everybody who’s listening to this to do what Laurie has done. And have a great number 2. Lori, you’re a great member. You are always willing to contribute. Today’s conversation was a big contribution, so on behalf of the members, thank you very much for coming on the show today.
Lori Turner-Wilson: Pleasure to be here.
Greg Alexander: Great. All right, so a couple calls to action. So if you’re a member and you’re listening to this, and you’ve got a million questions for Lori, we’re gonna double-click on it and go a little bit deeper on the private member Q&A session, which is upcoming on one of our role model sessions. So look for your meeting invitation for that, and please attend. If you’re not a member, and after listening to this, you think you might want to be, check out Collective54.com and fill out an application, and somebody will get in contact with you. But until next time, I appreciate you giving me your attention and listening to the show, and I wish you the best of luck as you try to grow, scale, and someday exit your firm.