Behind the CXO Title: Prioritizing What Matters Most with Will Cook

Anderson Williams: Welcome to Bigger. Stronger. Faster. the podcast exploring how Shore Capital Partners brings billion-dollar resources to the lower middle market space. In this episode, I talk with Will Cook, whose career includes time as a consultant, and then as an infantry officer in the United States Army today. Will is part of the Shore Capital CXO Fellows Program and works as Chief of staff at Skycrest Roof Co.

Which at the time of recording was in its first year as a Shore Capital portfolio company will explains what the CXO and chief of staff role looks like in an early stage company. One day he’s in marketing, one day IT, and the next day it’s whatever else is required to build the young business.

He shares how important it is as a young executive to really learn the business and build relationships with founders and partners. He also speaks to how important evaluating and managing talent is, even in the earliest stages of a company or perhaps especially so.

Will shares the moment he realized and processed the implications of the fact that in the roofing business, he will never be the hardest worker on his team. The crews putting on roofs will always outwork anyone. This means Will has to be that much more relentless in prioritizing his own time and work. To ensure he’s focused on what matters most and what creates the most value for those teams and the business.

Finally, will talks about the inevitable highs and lows in a young company, and the importance of his CXO colleagues and their shared experiences in maintaining steadiness even when it feels like he’s in the eye of a storm.

Welcome Will thanks for being here.

Will Cook: Thanks for having me.

Anderson Williams: Will you just introduce yourself, give us your name and a little bit about what you do and where you do it?

Will Cook: Yeah. I’m Will Cook. I’m from Winston-Salem, North Carolina. Went to the University of Richmond, had a little bit of a eventful career path.

Worked as a consultant for a bit, joined the Army, was an infantry officer, and now I am the chief of staff at Skycrest Roof Co. Skycrest is based in Denver and we have. Two different residential roofing companies. We have one in Longmont, Colorado, a couple minutes north of Denver, and then one in Englewood, Florida.

So split in time between those locations and doing all the things the chief of staff does. So. A grab one of those things.

Anderson Williams: Say more about that.

Will Cook: A grab bag of it all. I think I was the quasi VP of Marketing last week and we’ve hired a marketing consultant. My CFO and I always joke whenever there’s something that needs to be done, it’s like, well, we should get the VP of Technology on that, and we just stare at each other because it’s, you know, we’re a very lean platform right now, so you know, a little bit of everything.

But I always looked at the CXO program as sort of a grab bag of responsibilities, especially early on with these platforms. The biggest sin you can make right is build this huge corporate team and not have the revenue underneath to support it. And we’re taking a very conservative approach. We have a CFO, a Controller, and we have a VP of Business Development and me.

And so the CFO and Controller I think have their little universe and the VP of BD is definitely doing everything you can to get that engine going and to keep analyzing companies and then you name it, outside of that, it sort of falls on somebody else and that’s somebody else’s, sometimes me, and sometimes it’s my teammates, but I like that.

That was always an attractive part of the CXO program was you find a problem or you analyze something and you figure it out and you go in the business. And it could be something you have a lot of experience at and something you’re good at and something you enjoy. And it could be not. It could be something you’re new at, but it’s something that needs to be done.

Anderson Williams: So you have an interesting background in that you were a consultant prior to going to the military.

Will Cook: Yeah.

Anderson Williams: Just curious how that transpired, but then also how that prepared you for this reality that you’ve just described.

Will Cook: I was in DC doing consulting. I always felt like I had more in common with the guys in uniforms than I did, necessarily as a 23-year-old wearing a suit.

I felt, you know, I think everybody has a little imposter syndrome. And I certainly felt that, but I was also getting too old for something in my life. I, I sort of had the moments where it was like, you know, if I don’t do this now, I’m never gonna do it. It was something I had always been on my mind. My dad’s side of the family’s comes, uh big military family, so I think you always have the seed sort of planted in your mind.

But it’s funny being 10 years older now and being like, oh, I was getting too old for something. But it was the time. The big thing, my consulting firm is if you stay here for five or six years, business school will be free, but then you have to go back to the same consulting firm and all that stuff.

And I thought, well, you know, my dad did his residency through the Air Force and there’s other benefits to the military for sure. I sometimes felt like I’ve gotten more out of the military than I gave, but that’s again, imposter syndrome I guess. So yeah, I decided to go to Officer Candidate School in the Army.

You have to go to basic training first and Officer Candidate School and I remember I went to my unit, I was at the 101st Airborne. I was in the office preparing to deploy some guys in Africa, and they were running the most disgusting spreadsheet I’d ever seen. And it was sad. And I looked at these guys, I said, Hey, you know, gimme the afternoon. Let me clean this up for you.

And I did a V lookup or something, and these first sergeants were just blown away. And from then on, my battalion commander was a fan, I think. And uh. I had a little bit of office capability that some of my peers who had just graduated didn’t from that life, so that made my life a little easier. I think I was a little older too, so I wasn’t really wild. I wasn’t growing up. I was ready to be a professional and I took the job very seriously.

Anderson Williams: How has the CXO program itself, whether formally or informally with your colleagues, how has that supported your growth and your evolution into this role? Just give us a sense of that context for how the CXO program has set you up for success.

Will Cook: I really like the structure of development and sort of the once a quarter education sessions of which I’m coming to the end. I have graduated, but I really enjoyed sort of the structure. Maybe I missed school a little bit, but I like that aspect.

And then it’s always nice to have peers and something that I heard a long time ago is the higher you rise in a business, the lonelier you get. And while I love my CFO and my VP of business development, I deal with challenges that. They don’t necessarily deal with every day. So it’s nice to know you have a peer group where it’s like, Hey, have you ever seen this? Have you ever done this? How’d you do it? Do you have someone I could talk to who’s done this?

And so that network sort of plays on itself and having a curriculum that engages alumni, right? We have a couple alumni who I knew once as chiefs of staff and now their COOs and CFOs and the ability to sort of learn from our alumni and learn from staff, I think has helped to shape the curriculum and made all the sessions and stuff very tangible.

So, I think that’s the thing I look forward to the most, is just sort of yucking it up with my class. Right. And it’s always something that I knew I would miss when I left Shore ’cause I was there briefly of just like the SRT and everyone’s a young professional. Knowing the world of private equity, of lower middle market companies and talking about work and just hearing these really bright people talk about work is a great thing to do.

It’s cathartic in a way to hear people that I really respect and know and trust to say, yeah, I’ve seen a problem this way and here’s how we handle it.

Anderson Williams: And I imagine just from your previous comments, it’s some sustenance as well, right? It’s a more explicit form of learning, whereas you go right back into doing and executing in real world of.

Will Cook: Oh yeah.

Anderson Williams: The business that some explicit learning.

Will Cook: Oh yeah.

Anderson Williams: Probably feels like sustenance.

Will Cook: And that’s one of those things that’s a Shore-ism, right. Is working on your business versus in your business. And I think the CXO program is get your hands dirty work in the business. Knockout projects one at a time, especially in an early stage platform.

It’s pretty dirty and you’re getting in there, but it’s nice to sort of take a step back and work on yourself, on your leadership style, on thinking about your business working at a higher level. I think it’s something that I don’t always stop to say, well, how am I analyzing my own leadership style? Or how am I doing this today? Or how is the business from an operational structural point really doing?

No, I’m trying to get leads every day. I’m trying to look at the revenue every day and make sure, hey, what are we doing to get the results we need this week or this month? And it doesn’t hurt that we’re ending with a nice dinner. I mean, that’s, I’m a sucker for that. So.

Anderson Williams: It’s part of the experience, right? It’s, it is. I’m curious from your perspective, and it can be from your direct experience, but also what you’ve seen in your colleagues in the CXO program, what do you think makes a good CXO? If somebody’s listening to this and wondering, you know, is this an opportunity for me or is this something I would want to do? What do you think makes a good CXO?

Will Cook: Humility, I think is one thing, and humility and being a good listener play hand in hand, especially early stage platform. Having to go into a business and you realize that you are one of the youngest corporate members. You have the ear of the C-suite if you’re not in the C-suite yourself.

And that’s empowering on the one hand. But for me, I didn’t know anything about roofing. Right? And I needed to go in and learn the business, and if you’re not willing to sort of shadow every position, know what the office manager’s doing, knowing what the roofer’s doing, knowing what the inspector’s doing, then I don’t think it’s the position for you, right?

You really need to understand the business and be able to humbly walk in and listen and learn and then get to a point where you can provide value and give feedback and that’s one thing I think has really translated from the Army is the advice from commanders to young lieutenants is do not go into your unit and try to change a bunch of things.

And I have this idea, and I learned this in training and I did this and that has, I think, been the cleanest translation to the CXO program with this young platform is I would not have the relationships do with our market partners. If I had come in and said, oh, you should do this, you know, it’s like, oh, I know how to solve this. And it’s like, no I don’t. Right?

Anderson Williams: Lemme tell you what I know.

Will Cook: Yeah, yeah. I went to business school. Talk about something. No market partner wants to hear. “I have an MBA.” And so I think when I look back, I’m like, oh, that seemed very logical to me from a commander standpoint, and it seemed pretty logical to me from this standpoint.

And I think I’m really, I’m just starting to make that transition now, seven months in of, okay, I feel very comfortable in this business. More importantly, the market partners feel very comfortable with me and the business and the decisions I’m making, and I’ve started to see a little bit of a transition of and need to do a transition myself of, okay.

We’re past the learning and sort of observation mode. Now we need to start pushing towards integration and making sure we are making the right decisions and have the right people in the right seats. But none of those decisions can be done well unless you are present and spending time there and listening and observing and asking questions, and having a level of humility of why do you do it that way.

That’s one thing is learning the business. I think the other thing is personalities and knowing the people who work there and strengths and weaknesses, because this game moves very quickly, right? Lower middle market private equity moves quickly, and evaluation of talent is paramount.

And so unless you have evaluated or observed the talent in your company, well, you don’t really know who can evolve and grow, or who needs less responsibilities or who needs to focus on a certain thing, or even the personal side of this person is not here for the long haul, may have been transparent about that. Well, we need to find a solution that is, and so that would be the other thing I think I’ve been pleasantly surprised of is what a interpersonal business, this is what a people businesses space is.

I think a lot of time when people hear private equity coming in, they think of the nameless, faceless corporate drone dropping in, but these businesses are not that size. This is, I think that’s one reason why they hired you, right? I mean, that’s your background is the interpersonal side of business and making sure as a corporate team, we are leading, knowing the people we’re leading. Because without that, you are the nameless, faceless corporate drone and you’re probably not gonna last.

Anderson Williams: You’re not gonna last at all. Yeah.

I want to, to double down, I’m just taking notes over here and thinking about the people business, and you’ve mentioned humility and you’ve talked about industry knowledge and relationships and to some degree, intuition and experience to know why we do things the way we do things, even if it’s not documented and so forth.

Shore, no only prides itself on, but has been recognized for being a founder friendly, private equity firm. Can you talk a little bit just about the specific relationships and navigating some of that with your founders who have built great businesses?

Will Cook: Yeah.

Anderson Williams: That obviously we wanted to partner with but they also have legacies. They have teams that look up to them and have been answering to them, and now there’s this new like corporate entity that’s this. Can you just talk a little bit about that unique relationship with the founder?

Will Cook: Yeah, I can. I think it starts with, Shore. I don’t know how Dan, Shannon and Enzo did it, but they picked two great founders for us to start with. So we have Ryan in Colorado, Dan down in Florida, and. They’re great people, which makes everything easier.

Roofing is also, you know, like private equity. There are bad businesses in the industry. They’re just like the reputation of private equity coming in, stripping value. There’s roofing businesses that don’t care about their customers, that don’t do the right thing to your home and leave people high and dry, and we are not that type of business.

We do the hardest things the best. Which is a high quality roofing job on every job, high QC and safety. And so that has made it much easier. Right? I wish I could say there was some challenge or unlocking of character, but it’s not there of the utmost high character. And that shows, I think, Shore system from a BD standpoint of really identifying the right people to partner with.

So my journey was I may be the earliest CXO on a platform ’cause I joined a week before close. And so I immediately moved down to Florida to Englewood for about two months and we closed on ACL roofing on a Monday. And then a category four hurricane came on that Wednesday.

And so, uh, baptism by fire a little bit, but a great example of Dan and Kenya who are husband and wife, who are presidents of this business, was I had evacuated the flood area. The counties was on the phone with them talking about work and said, you know, I’m trying to figure out when to come back, but I can’t. I don’t know if I have power or anything like that.

And they just go, oh, we’ll go check on it. We’ll go check on your rental. And they drove over, called me 10 minutes later, said, yeah. Somehow you’re good to go. Power’s on no flooding. Street looks clean and the area had been banged up a little bit and that just showed me sort of their character, but I think it also showed them I was eager to get back down. I recognized that this was an important time for their company, for their community.

What good are you as a local roofing company if a hurricane comes through and you’re not willing and able to be there and support your community? That is what they pride themselves on. They are a community driven organization, and so I think they really valued the presence.

And so the same thing happened December 1st. We closed on our Colorado business and I went up to Longmont spent almost every day there for a couple months when I wasn’t in Florida. And again, learn the business, learn the people, and was present. And I think they feel more comfortable because I’ve been there, because I’ve set in the seat and observed how the business functions.

Anderson Williams: So you’re here in Nashville for Music City in May, our annual gathering of the CXOs, and there’ll be some new people.

Will Cook: Nice.

Anderson Williams: In the mix. What advice do you have for someone who’s maybe just joining the CXO journey or just joining a new platform? If you had to summarize some of your thoughts into some advice.

Will Cook: Yeah.

Anderson Williams: What would you offer?

Will Cook: Well, we talked about learning your business. That’d be number one. Learn your business. And there’s gonna be a lot of small projects and tasks and fires to put out, but you have to maintain sort of understanding your business. ’cause without that, nothing else is going to fall into place, and you’re not gonna be making informed decision.

We talked a little bit about, you know, know the people you work with and for know their personalities, know their quirks, know what they’re about outside of work. It makes everything a lot easier and makes you a real person.

You know, the other thing I would not, and we sort of allude to but’s be a connector, Shore hosts these events to connect us as a class. The peer connection is real, but you should be aware of what resources are available at Shore. You should be aware of what resources are available at your corporate team. You should be aware of, you know, if you have a location in Colorado struggling with one thing and recruiting. You should know if that Florida business starts struggling as well, that there’s someone that they can talk to and there’s a peer that they can have, like we talk about, the higher you rise in the business the lonelier gets and making sure that the peers are connected across your portfolio company.

And then, you know, one piece of advice that I need to constantly. Think about, it’s just thinking about the value, whether that’s EBITDA, revenue and how that attaches to your initiatives. If you are spending a whole lot of time on an initiative that’s not driving value, you need to think about if it’s worth your time. That’s something I’m saying out loud to give value to myself ’cause it’s an everyday sort of analysis.

I have been working a lot and definitely feel that I need to do better at that, but that would be my main four, is learn the business and the people. Connect those people. And then when you think about your tasks, start to really analyze, look at your P&L, understand what’s driving the business, and start in places where you think the biggest lift is available.

Anderson Williams: Yeah, I’ve had a couple of interviews with CXOs, even going back to last year where the term relentless prioritization.

Will Cook: Yes.

Anderson Williams: Has come into play and that’s what I’m thinking about as you’re saying that last part.

Will Cook: I have on my to-do list, like go through my Shore notes and pull out, but that’s one of ’em, you know, pull out the lessons learned. Relentless prioritization is one of ’em, and it’s tough, right? The more ingrained you are in the business, the more issues you see. I think it was Mike Aubrey or someone says, you have to be relentless in finding holes in your business and prioritizing those holes is an ongoing effort. There’s no such thing as the perfect business, right?

Anderson Williams: No matter what your background or your Type A needs, there is no, this is the reality, right?

Will Cook: Yeah. I’m racking my brain. No, I, yeah, maybe, uh, the local Chick-fil-A, but that’s, uh, yeah, yeah.

Anderson Williams: Yeah. So. One of the questions that I’ve started to ask everyone, what’s the best advice you’ve ever gotten?

Will Cook: Hmm.

Yeah, there’s one piece of advice. For a while. I was a political science major, like we talked about. I thought I wanted to work on the Hill, be a politician, and I was working for this lobbyist in DC and he said, Hey, I need you to go to this hearing and get me this paperwork. And I said, well, you know, the paperwork’s only for media. It says.

And he sort of shakes his head and he sits back and goes, well, if you’re dressed appropriately. And you act like you’re supposed to be there, no one’s gonna say anything to you.

And that advice, you know, it sounded shallow at the time and hilarious. And I did. And I did go to the hearing and I did pick up a piece of paper and I looked around and no one cared one bit, even though they all probably knew I was a sweaty summer intern in the DC summer.

But it was true in that there’s a difference between like hubris and confidence, but in some ways it’s sort of cathartic for the businesses you partner with to have young executives who are confident. And so going in there and making sure they know that you’re confident. But again, if you are learning your business and being on the ground, that will not be confused with sort of this hubris of, oh, I know what’s going on.

But having that confidence and just being able to assert yourself and pick your spots, I think is great advice. I try to think about that whenever I go into an interview. Is, I’ve been screened to this point when I, I was nervous at Shore. I’d never worked at private equity and I remember that advice, right?

Well, what’s the easy stuff to get done? Dress right, you know, I can do that. Okay. It’s again, Army parallel is show up on uniform, be on time, and everything else can fall into place. You can really, as a young 18-year-old, you can really be successful there. If you do those two things. Show up, dressed right, bring the right stuff, be on time.

That’s like 80% of the very beginning of it all, even for young officers. And I think it rings true in this world as well. The best advice. Yeah, it’s just show up dressed, right. Act like you’re supposed to be there. And if you do it correctly, people will know that you have what it takes to at least be in the room. And if you’re smart, you’re listening when you’re in the room and you pick your spots.

Anderson Williams: I can’t help but think there’s another side of that though. Will, we’re going back to your comments on humility because there’s also a side of that that’s showing up and dressing right when you’re showing up at a job site.

And you’re learning the roofing industry. You’re not showing up in your suit and tie. You’re not showing up looking like you’re from corporate. You’re showing up and saying, Hey, I’m in your territory. This is your zone. I’m the outsider. There’s a humility side of that too. Because to take for granted that it works the way that you were describing but you show up dressed the wrong way and going out into the field or to a frontline team member, that’s a good way for them to just write you off.

Will Cook: Yeah, roll their eyes. Yeah. I mean, they’re 7:30 AM production meetings every time in Florida, and I do not need to be there, but if these guys are there, you know, planning the day, and these are the supervisors, I need to be there. I need to show up.

And I was talking to the seller of the business there that it’s, the hardest part about the industry I chose is I said, you know, I’m never gonna be the hardest worker at this company. And he looks at me, he goes, not even close. He goes, these guys are out there. I mean, a shingle space barrel tile roof is like their money maker down in Florida.

Now these guys are lugging 25 pound tiles, placing ’em in the Florida sun. They’re working all summer. The least I can do is show up to a 7:30 meeting or put in my time work hard because those are the people who are really providing the value and really the engine of the company and I think hard work is the only thing you can’t teach.

And yeah, there’s a lot of great ideas and people, very loud people with great ideas, but that’s a dime a dozen in my opinion unless you’re rolling up your sleeves and working at it, a lot of ideas fall away, wither away.

Yeah, it is people business and knowing who those people are. And there is a luck aspect and there’s a lot of highs and lows, and sometimes a ball bounces your way and sometimes it doesn’t and a big part about this business, I think rings true with sort of a career and the military is very rarely are you gonna benefit from a good bounce every single time. A lot of times there’s things outta your control, whether it’s the market, whether it’s losing a big customer, you just have to adjust.

It’s playing, they love sports metaphors here, which resonate with me, but it’s field in a ground ball, right? Sometimes, uh, you have to adjust, you have to get in front of it, and you have to be able to make the play. And I think that’s one thing that I’ve learned, but is again, a constant reminder of can’t get too high and too low, and you have to sort of stay level, but that’s also the point of the CXO event, right?

Like it is nice to come in here and come into Shore and see friends. I know peers, I know a ex-business school professors like Anderson and the CXO program is built as we are building the next C-suite of these companies. And I take that very seriously and that doesn’t happen overnight. It doesn’t happen in one year. It happens over many years, over many experiences. And you have to weather the highs and the lows.

Anderson Williams: If you enjoyed this episode, be sure and check out our Bigger. Stronger. Faster. episodes. Specifically highlighting the CXO Fellows program as well as other CXO Fellows profiles at www.shorecp.university/podcasts or anywhere you get your podcasts. This podcast was produced by Shore Capital Partners and recorded in the Andrew Malone Podcast studio. With story and narration by Anderson Williams. Recording and editing by Austin Johnson. Editing by Reel Audiobooks. Sound design, mixing, and mastering by Mark Galup of Reel Audiobooks.

Special thanks to Will Cook.

This podcast is the Property of Shore Capital Partners, LLC. None of the content herein is investment advice, an offer of investment advisory services, nor a recommendation or offer relating to any security. See the Terms of Use page on the Shore Capital website for other important information.