Finding (and Keeping) High-Performing Sales Teams, with PE Assist

Let's be real. Finding good people might be the hardest part of running a roofing business.

Meet Dan Cherry, Mea Dawson, and Chris Serignese from PE Assist. In this Masterclass, they discuss with Pete why roofing companies struggle to hire and retain good people… and how smart, structured, repeatable systems solve it.

They cover:

  • Connecting your business model to the right talent sources
  • Creating a first-class candidate experience
  • Structuring your interview and training processes
  • When to hire outside of the roofing industry
  • Building credibility and keeping employees motivated

If hiring and turnover keep you up at night, this one's for you.

Pete: All right, we're back. Welcome everybody to the Roofr Masterclass. I am your host, Pete McKendrick. Thanks for joining us again here if you are a return guest here to our Masterclass. If this is your first time, then welcome. Excited about this topic today and excited for our, our guest panel here. Normally we have maybe one guest, if any. So pretty cool to have a panel of you guys here today, so excited about that.

This is one of the things that I think comes up the most often. Hiring and finding good people along the way can be a challenge and, and continues to be a challenge for this industry.

So, Our guests today, Chris, Mea, and Dan with PE Assist. As always, I am your host, Pete, with the easiest email at Roofr, pete@roofr.

Let's talk quickly about you guys, right? So I'll give you guys a chance to introduce yourselves, talk a little bit about what PE Assist does.

Dan: My name's, Dan Cherry. Me and Chris are both founders. Me and Chris met he was the director, national director of recruiting for the sixth largest exterior company in the country. I worked in Minneapolis, which is actually where the headquarters was, but Chris was so good he ran operations out of Orlando.

And then Mea was also part of that organization. So, me and Chris have both worked with companies that have sold. Because they put structure in place, they were able to scale. Chris has gone up and down the East Coast, but mostly, Florida. Myself has been more in the Midwest, Minneapolis based.

I've worked out Utah, Washington State, down to Texas, over into Pennsylvania and, and a lot of places in between, helping sales reps you know, get into this industry and, and make a lot of money. And so that's a little bit about me. I'll, I'll pass that over to Chris.  

Chris: Yeah, kind of got into roofing randomly in 2013. I was actually just starting my grad school program and just fell naturally into recruiting. And so I quickly realized I could kind of help scale the company through bringing on the right people and building processes around it. I think I did the seventh roof in the market, and a few years later we were doing about 50 million in revenue a year and consistently stayed there.

And then I went on to Legacy Restoration to help them with their processes and, and we essentially combined three companies, Legacy, Janney, and Southern into one and took over all those recruiting processes. You know, PE Assist, we kind of went with PE as like private equity, but really what we do is we connect people with exterior contractors.

I think all three of us could say that our passion is, is helping people get connected with the right contractors and really excel in their role, make a, a really good living and have a good quality of life. And that's something we've been able to do on our own and even with the companies we work with.

So that's something that, we really enjoy doing. Cool.  

Mea: That leaves me. My name is Mea, as you can tell. I'm right there with Chris. I believe we all share the same passion in helping people. I've been in recruitment for over five years now, going on six five of which I've been in that construction roofing scene, which kinda found me.

But my passion being helping people, I found construction and I was like, "Oh, this is perfect." So I've, been recruiting, across the United States for quite a while, and I put emphasis on that because I myself, I'm located in Belize, which is Central America. So I get to help out from afar, but I love where I'm at.

The hiring and recruiting process can be very nerve-wracking for people who are seeking employment. I'm happy to be that person to make the process a bit more seamless and comfortable, from start to finish. Awesome.  

Pete: Yeah, I love this, you know, 'cause we obviously, process, it's in my name, right?

Process is a big thing for me, and you guys all mentioned it. So many companies are either looking to sell to PE or, trying to survive in a time where right now, you know, the market's been down a little bit because we really haven't had a whole lot of storms.

And what you're seeing is some of these companies that don't have great processes and systems in place are struggling. And here's one of the things that I think never, quite honestly, never gets talked about the hiring and the recruiting process, right? And even the training part of it, right?

This is something that I think it'll be important today to really stress the fact that, yeah, we build a process around, how we handle customers and how we handle production, but we should have the same idea behind how we hire, how we train, how we recruit. I think that's gonna be the biggest takeaway from all this is that I think traditionally we don't necessarily put a lot of emphasis on having, like, a really structured process to bring people in, get them trained and set them up for success, inside of smaller roofing companies especially.

A lot of these companies probably in the midst of a really busy season right now potentially seeing some turnover, especially in sales.

I know a good friend of mine is based in Florida, he's constantly looking to hire new salespeople and, kind of has a bit of a revolving door there as he gets people in and out trying to find the right people.

So I'll let you guys get into it, and we'll just kind of talk through things as you guys go.

Dan: Yeah. Great. You know, first thing we'll just start off again, a little bit of introduction as to who we are. PE Assist, me and Chris have helped so many companies sell out and I'm sure many of you guys have worked with a company where you had to make a move, where you had to leave and you're gonna leave money behind, right?

You had either plans, whether you were forced out or whether you just had to leave for the right reasons. And, that's where me and Chris have found ourself multiple times. Once you help a company build so big and you're hiring the right people, they might not need you anymore. So PE As- me and Chris teamed up with PE Assist, so that we didn't ha- didn't have any reason that we had to leave our own company, if you will.

And to build something special and to build something that, we've worked on recruiting projects and, even after a a year of working with a company, we actually can get twice as good the second year 'cause we know how they operate. We've been, working with them on some systems to in place and to put other things.

And then, you know, that, even that, getting into year, three, we've been able to connect them with local pipelines that, you know, if right now we're new to Indianapolis but we've dove in hard, you know, and we're finding new pipelines of where people that they're looking for match what, you know, the candidates that they're looking for there.

We are, you know, real people that are doing real resumes and, and really adding to a team. And we don't charge we're not charging for our consulting.

What me and Chris get down to is just charging for people that bring in ROI or return on an investment is our stance on where we are. But to help a lot of our contractors get to that, we have to put systems in place. So what I wanna hand off, over to Chris here is, just talking about systems and what you really need in place to, to even think about adding more than three people, more than four people onto your team. So I hand it off to you, Chris.

Chris: Thanks, Dan. I think one of the biggest misconceptions in our industry is that scaling means hiring more salespeople. You know, it, it really doesn't. I think scaling means building a hiring system that consistently attracts the right people and developing them into top performers, right?

So, it's not like a knee-jerk reaction where, "You know what? We need more revenue. I wanna scale. I, I wanna hire more people." It's really building a system around it where you can confidently bring people into it that can be successful, and so that goes into what is your interview process, right?

And just having a first-class interview process for your candidates is huge because if that doesn't go well, that says a lot about the company, and that will scare off a lot of really good candidates. But even after that, you have to have a really good onboarding and training system because you can hire, great people, but if you don't have the ability to train them, they're not gonna be successful.

You know, and then understanding your business model. Are you retail? Are you insurance? If you're retail, do you have leads that you can provide? Are you giving the salespeople tools to close? If you're insurance, is there a storm to work? What are you doing to do that? So I think sometimes contractors get ahead of themselves in hiring without having, the systems in place.

When we meet with clients and contractors that need help hiring, we wanna really get to know them. We wanna spend a few hours getting into their business, understanding their goals, and then really kind of coming up with a custom package that's gonna suit them.

So, it's not just like we're gonna post an ad, we're gonna hire some people, and we're gonna get them in there. No, we, we wanna make sure if we're gonna work with you that you have some of these systems in place. If not, we can help you with those. That's more of, like, a consultation piece. But if you do have all those pieces and you're ready to hire, then that's something that we can sometimes just jump into and get some job listings up, reach into our own network of people, and get you going with some hires.

But I think the first thing is having a really solid foundation for your business before really jumping ahead into the hiring process.  

Pete: a question here from Brandon that kind of plays right into what you're talking about right here and he said, "If you're putting systems in place regarding charging based on ROI, do systems encompass mostly the hiring process or putting in place trainings that will keep onboarded reps and provide them the structure and tools to take off running and produce revenue and profit?"

Chris: So when we're interviewing applicants and getting them set up to interviews, like we're gonna share them some tricks of the trade, and kind of help start their training process, but that kind of goes back to what I just was talking about. In our first meeting with you, we wanna know everything about your training processes.

If you don't have them, then we need to help you build them. We can't really hire for you until these are in place. So if you want our help doing that, we have a playbook. We can roll that out.

Where if you're using us to hire, we have a guarantee. With most contractors, we work out a time limit, and we're with that candidate, checking in on them daily, weekly, monthly until they hit that time limit. But we're there making sure that they're being successful or that they're getting an opportunity to be successful.

And if at a certain day and within that time limit, if that person doesn't work out, then we have to, refill that person at no cost to the customer or the client.

Dan: Yeah. For any of the contractors we're working with, before we start hiring, we figure out what their systems are.

Because One thing I love about the industry is, number one, there's a lot of profit in it, which means you can pay a lot of people a lot of money, but you could also work the job the way you wanna work it, right? So there's companies out there that just pay people to sign contingencies.

They don't do any of the rest of the job, right? So figuring out even what your people are doing in your company and how you want that process to go. I've worked with companies where one guy signs contingencies, they have somebody else meet the adjuster, and then that same person that signed him up help place the order.

And I've been with companies where they got a guy that just places the order, right? So there's three people involved with the whole process. The one thing that I think we bring to the table is also just talking about what's your strengths? How do you want this to play out? Are you having somebody do the whole job?

Because instead, when people are applying, people like me, Chris, and our recruiters we know the programs, right? So we're able to describe, "This is what your day-to-day looks like. This is what you're gonna do your first year," to get to the right point.

So if we're working with somebody we know kind of what they're going into. And then if you could think about that as a contractor, where you're getting an email from us saying, "Hey, here's their cover letter, here's their resume," they're interested in doing what you're asking for. Maybe you hate having the conversations where you gotta say, "You don't qualify," that, "I don't think you'll make the cut."

I mean, if you could imagine Chris doing the first phone call with these people in a virtual explaining what their job's gonna do before maybe a contractor that's never been a part of a 12-person team before, you know, those are kinda cool things that we help and make sure is established.  

Chris: And something we do in those first calls are we build out our own kind of proprietary private website for each client.

So we're gonna share and review this webpage with the candidates. And so on this first call, I'm gonna share my screen, and then I'm gonna go into a little bit about the company what the job is, what the responsibilities are, and I'm gonna say, Are you willing to do these things?"

Explain the pay. We're gonna have links to the company's website, YouTube videos, Instagram, whatever it is. We're really there to kind of, like, build credibility for the client, but at the same time weed out people that aren't gonna be good fits, and that way we're gonna save the client a lot of money and time.

'Cause at the same time, like Dan was saying, you could hire a recruiter for 100 grand a year, right? And they're gonna do all of these things we're talking about. Or you could hire a company like us and spend 40 to 50 grand a year and get a lot of hires, and we're gonna guarantee all of them, and you don't have to have it done in-house and you don't have to spend your own time weeding out these bad candidates.  

Pete: Even from our perspective, like, obviously the goal at Roofr, from a software standpoint is to streamline your day, make you more efficient, make you more organized, make it easier for you to get through the day, and kinda help with the remedial tasks, right? To help you kinda get rid of the stuff that's time-consuming, that's repetitive.

I know hiring is a thorn in so many people's side because it does take a lot of time, and especially if I'm a small business owner, I don't really have that time to give. I told, a story earlier about a company that I was at the person was hired and they were kinda, like, thrown right into the fire because the other people around them just don't have the time.

A-And a lot of time that's how things are, in these offices. We totally get it. That's where you guys can kinda step in and help them out. Love the process, love the systems piece. Obviously we stress that like crazy on the software side because, same thing w-with software as it is with employees, they're only as good as what you put into them, right?

And so if you don't invest the time and energy to set them up correctly and set them up for success you're not gonna get out of them what you hope to get out of them. Who's up next?

Dan, you got something? Oh, Mea's got something. Mea's gonna talk. This is my favorite part right here, Mea.

Mea: What I wanted to focus on, in calling back on what I mentioned at the beginning of this webinar is you know, that candidate experience. I like to tell my candidates, you know, as much as I'm interviewing you for this company, you need to keep in mind that you're interviewing us as well.

And so I wanna set that standard, and from the jump, my goal as a recruitment manager is to understand what your company's looking for, what the culture is like, what the expectations are. If I were looking for a job, I'd need to know all of that before making the right decision. Not only that, I'm probably applying to a bunch of different companies, so I need to have all the information that I need to make the right choice.

And so the system that we have in place is coming prepared with all that information, asking the right questions, getting a feel of, is this candidate willing to do what they're being asked of? Is this candidate a, a right fit for the culture at this company? We're weeding out all these fine details before even presenting them to that company.

Most of the times these are sales managers that are also in the field. They're running appointments, they're training, and so you don't, probably don't have the time to do six interviews a day. And so we're, we're saving you some time on that, and then sending you people who we've already identified that they wanna be here and they wanna do it for the long run.

Another topic that I wanted to touch on, and I believe Pete had mentioned it, you know, where do you find candidates? And he's right, we're there's no set blueprint for this. You know, around graduation time, going to colleges and trade schools might be a good hit.

So it oscillates throughout the year, and it's just knowing where to look. There's also aspects like having the right applicant tracking system, which can be costly. There's also having to invest in the right job boards, which might not be the right place for what you're looking for. And so especially since Dan, Chris, and I have been in the industry for quite some time, we've got a knack on where to look, but of course it changes.

There's no one way, but we have the places that we'd like to look once we know what you're looking for.  

Pete: I think that, we often talk about the customer experience on our side, right? We stress the customer experience and I say to contractors, like, "If you were the customer, would you hire your company," right?

And I think it applies in this situation. Like, if you took a step back, if you were looking for a job and I started to research your company, would that be a company I would wanna work for, right? And I think that goes beyond just, them applying and you interviewing them.

How are they finding you? What are they finding out about your company? If I Google your company or throw your company into ChatGPT, what's it gonna come back with? If I go to your website, what am I gonna learn about your company? And, am I gonna feel like, "Hey, this is a place where I wanna work"?

All that stuff has gotta be thought of, right? In today's day and age, it's so much easier for me to go and find that information and to do a little bit of homework. We hire people all the time at Roofr, and people go, "Oh, I feel like I know you," because they've already watched me on YouTube right before they've even come in.

We've already put that forward. And so how familiar are they gonna be with your company before they, they come to you as an applicant, and how comfortable are they gonna be?

Is it a place that they're excited to interview and wanna work, or is it someplace where they're, like, already hesitant, right? Could change the whole focus.  

Mea: we do make an effort to let our candidates know when reading a job description or when we're reaching out to them on a cold call, this is who we are.

But really we're promoting whichever company we're hiring for. So if it's Roofr, we're, "This is the facts about Roofr. Are you interested? Let's talk about Roofr. PE Assist is here, but let's focus on Roofr, what they have to offer, what their benefits are, what the culture is like," and we're really getting them excited and informed so that they know what they're signing up for.

That's... I like to think about it from if I were looking for a job, how would I want this conversation to go? Do I try to make sure that before I even hop on a call with an applicant or a candidate, I'm asking these questions.

Dan: I'll give a free prize to the first person that writes in, what type of lead is the easiest one to close? I'm watching the chat right now.

Referral. Thank you. There you go. Imagine you're talking to a profe- i- if you're an applicant, you're talking to a professional company and they really give you some great details. 'Cause number one, we know what ... we know 'cause we talk to them all the time.

"I'm looking for this," or, "I'm looking for that," or, "I'm looking for this kind of opportunity or that kind of opportunity." Then imagine we say, "You know what? I think you would be a great fit for this company right here." We'll just use Cornerstone. We think you'd be a great applicant for Cornerstone, and imagine them going into that next interview feeling that

This is a referral essentially with somebody that thinks I'd be great at this and good at this. I think that adds as well.

I'd say one of our biggest pain points is actually getting that applicant through the interview process with the sales manager that's maybe not used to interviewing.

Maybe they need some interview training or they need a, something else to understand this experience. But Mea, what do you commonly see to give some tips on, if you do have somebody that's applying, where are you seeing a lot of spots that really turns off applicants?  

Mea: It's really case by case.  

One of the ones that we've seen is just not getting to them in time. I mentioned earlier, if you're looking for a job, you're not just applying to one place. You're applying to all the roofing companies in your area. You're applying to maybe even a retail job just because you need to put food on the table.

And so it's getting to them as quickly as possible, getting the questions that they need answered which would lead me to another pain point, which is, not everybody knows what the structure of an interview should be. It does differ, but if I'm not hearing what I want to hear on that initial call with a company, my thoughts are, well, they're not the right fit for me.

So in that initial touch point with them, it's finding out what are you looking for? What's important to you? What will it take to make you say yes to a company? And, and tying it back to, you know, as much as we're interviewing them, they're interviewing us. So really finding out what is it that you need to stay with a, or make that decision to switch companies and stay there for a long time.  

Pete: And it's about hiring for a brand new company, right?

Because you don't have the track record, the referrals. You don't have the clout maybe to be able to entice people in, the reputation. So what are some of the challenges there and how can you overcome those as someone who potentially has started a brand new company and wants to, to hire?

Chris: If you're going into that role as a sales director, I'd first wanna know, like, "Hey, what is my resources with this company?

What is my budget?" Maybe it was a company that you could have done a little bit more investigation on and see if it was gonna be a good fit for you. 'Cause you definitely need those resources while you scale. But I think starting a new company, it's, it's telling your story, right?

Why did you wanna start a new company? Because you found that the contractors in your market are doing bad work and you wanna really bring this quality of work to the market that's never been seen before, or is it because you wanna offer this opportunity to salespeople and you wanna run it a different way?

Being a new company isn't a problem. My... I have a roofing company that's fairly new. A lot of people, I just share with them my story. "Hey, you can check me out on LinkedIn. I've been in the roofing business for over 15 years.

I've helped start X, Y, Z companies. But what I found working with those companies, was "we don't really have control," or, "The company I was with was scaling in such a way that they sold and I lost that opportunity," right? So I would explain those things to people.

Tell your story, get a foundation, right? Start with a CRM like Roofr, and then start getting some other pieces in place that's gonna attract talent, right? And then for us it's not that hard of a sell to get somebody in new if you have a good offering, right?

If you have a good comp plan. I could probably find a manager for you to help run your business if you're willing to pay him. That might be something for him where he can kinda start over and gets a chance to build something, you know? And I think for a lot of people, when they're leaving a company,

They don't wanna take a lateral move. So if they're leaving a fairly large company that they don't have opportunity at because of hundreds of people that work there and whatever's going on in the background private equity or different leadership things, right? This might give somebody an opportunity to be like, "I wanna go work for a smaller kinda mom and pop where I can be a part of the change, where I can be a part of the growth."

Dan: Yeah.  

Chris: 100%. "Where I'm gonna have opportunity. If I stick with this for a year or two, I'll have 50 people underneath me on my sales team," you know? Eh, so we have to kinda figure out what your goals are what your story is, and that's what we kind of put into that proprietary website that we share with candidates.

It's all to build credibility for you. But at the same time, they're gonna be able to click on our links and say, " oh, Chris and Dan, they've been in roofing since 15 years. They're not just gonna work with some fly-by-night contractor." And at the same time, if you're a new company, that's where you wanna make those alliances with, like a Roofr or get with a manufacturer that you trust that you can become some sort of certified with, right?

So I think it all just comes down to getting the right pieces in play before maybe hiring people right away.

Pete: Yeah, and I think one of the things to note here, 'cause I've seen contractors go through it too, is sit down and write down what, ultimately what the mission of your company is.

Like you said what are you doing? Like, is it to offer better quality? Is it to, hire veterans only, like, and give them a place to work? Whatever that is, be able to have a clear story, right? Be able to convey a clear mission so people coming in really understand what they're getting into.

I don't think it's a hard sell to be a new company. There's a lot of people I think that would love to step into a role, like you said, maybe leave an established company and go back and have more flexibility to be able to do a little bit more.

Sit down, write this stuff down, and really hash it out beforehand, you know, because, "Hey, I wanna be rich and I wanna make money and scale to a $10 million roofing company," isn't really a mission, right? Make sure you have a clear direction that people can buy into.  

Dan: Yeah, and I love working with small companies, especially if you don't even have an office.

The, so the first interview is actually in the field at a build. Like, that's the best place to interview somebody.  

Chris: Yeah.  

Dan: Show them, "I just made money doing this. This is how I got this," get them sold on that, and then you have, generally, if you don't have that much overhead, you can pay them more.

Or you've got, maybe you gotta set up a budget for their first whatever you gotta think you got offering. Again, I think different territories have different competitive compensation plans, so, understanding what that is is important. At the same time, if you're able to work with people that are, maybe don't know roofing, but they're great people, and they're great motivators, and maybe they've sold something at a high level before, those people don't know the difference.

Chris: Yeah.  

Dan: You're just going over the opportunity with them, and then like Chris said us leaving the sixth largest company, we probably don't wanna go back to the largest company. We wanna be a part of starting something special the right way, and taking the experience, Brandon, that, that you have, I'm sure you're like, "I wanna start it my way, because I know this is the right way."

You know, having some extra people in your corner might help.  

Chris: We actually have a client in, the Tampa area, and he worked for one of the largest retail contractors in the nation before getting his own license, starting a company a few years ago. I think about three months ago, we made our first hire for him, and the guy's doing great.

And now we're sending more interviews to him. He wants to get a second hire made. And just, like, a week or two ago, he, he's in a new office. He's not working in his home anymore. He's got a brand-new office. They're scaling. They're doing all these cool things. And now what a great story to, somebody can come in and say, "Yeah, last time I had an interview I, I met him out at Starbucks, but now y- you know, we have this brand-new office you're sitting in."

So we're seeing that quite a lot, and I think, roofing's already that way. It's a highly segmented business. There's a lot of people that get into sales or labor, and they think they could do it better for whatever reason. But I think, like Pete said, if you have good intentions, and you have a good story, and you have, good processes, you can build something great.

Pete: Now how often do you guys see people from outside the roofing space, being placed inside of roofing companies?

Dan mentioned, you know, people not having a roofing background and not necessarily counting them out. I had a roofer one time say to me, "I hire all of my new people from Chick-fil-A because they have incredible customer service backgrounds, and then I teach them roofing."

How often are you guys seeing that and how successful is it to hire just outside of roofing altogether?  

Chris: yeah, we would pick up people at, hospitality places, and valets, and golf, you know, golf courses. And there, a lot of times there's people that just need an opportunity to do something better than maybe working in this hospitality job, right?

Not that there's anything wrong with that, but it's a better quality of life when you can kinda work Monday through Friday, 9:00 to 5:00, be off on the weekends and the holidays, and have really full control of what you can bring home, what you can make.

And so I'm always just looking for somebody that's, you know, talkative or friendly. But over time, I realized you can only scale so far with that. You have to have a process around it.

But I think good people just naturally gravitate towards good people. So if you're someone that can pick up a conversation with a valet guy or, or a, a fast food person or a restaurant person, like, you're probably gonna be able to hire quite a few people that way, but how many can you really do, right? You have to have a system in place where, going back to the beginning of this year, what is your goal in revenue?

How many people is that gonna take? How are you gonna split that up? Well, you probably are gonna need to hire, based on your math of a per sale job, right, like how many people is that? Sometimes you gotta reverse engineer it a little bit to figure out how many people you wanna hire, and out of that you might be able to hire a couple off of your normal everyday occurrences.

Dan: Again, a reason that I'm super happy that we have PE Assist is me and Chris can continue to build now pipelines. My goal as a prior service Marine as far as out of the industry, is to hire more military people than, let's just say, civilians that are inexperienced next year.

Talk about people with discipline, talk about people that have never even thought about roofing sales, 'cause it's not a job in the military, and the pitch to make six figures getting out of the military, if you didn't know, most people in the military, their families were not wealthy.

These are people that are like, went to the military for a reason to get out of certain situations, and they just finished four to five years, maybe 20 years. Our most recent guy just finished 20 years. He's a officer, and he just started at a roofing company the other day.

So we're able to do that, while, think about it, a contractor with four or five sales reps, are you really gonna focus all your time on getting to know all the nonprofits that help people getting out of the military? So those people are very coachable, and that, which dives into the next thing.

So my segment's a little bit more on the retention, right? So we hired the right people, now are you prepared? Do you have a 90-day plan? So these are like things that with our customers, we share these plans with them because we know they work. Chris and me are pretty heavily on recruiting for people to start in the insurance restoration side, Not on retail.

Chris: Well, retail is just having an in-home sales process. It's having financing. It's how you take your lead in from the beginning. Are you setting your appointment with, with both homeowners there? I could give you a really easy playbook to follow for retail, and you have to have financing.

But can the people do it in the house? You know, that's a whole nother question.

Dan: Then imagine if you're an applicant, you've never even been in the roofing industry. And I will tell you, even the guys that have been in the industry,

They don't know what they don't know, that's for sure. And a lot of the times I see people hire a guy that's done a million only, or has done five million. They come to a company, and they're just, like, given no structure. They've not given that attention for 90 days. You're not getting them to their five plus deals as fast as possible.

Gen Z people right now, 87% of them will quit their job within the first 12 months. 87%. And by the way, I think those are gonna be your hardest workers if you can retain them, because they haven't cut their teeth yet.

These are the inexperienced people, the younger people are the ones that are gonna be able to go out there. What I know Gen Z people want, and I know what military people want, is they wanna know I'm coming to a job that I actually know what I'm gonna do on a, I don't even need to say day-to-day basis, but what's my schedule gonna be?

How are you gonna make me successful, and do I understand that? So if I'm able to tell a incoming sales rep, "Hey, your first two weeks we're gonna do a lot of job shadowing. I'm gonna be taking you out in the field. That's what it is." And I put it in their calendar. Your trainer, your sales manager should own their calendar.

If you just wanna be like, "Hey, if they can't figure out how to run their calendar, they're not a good fit," well, you guys are gonna have a lot of turnover, period. Criticizing them because they don't do something that's natural to them isn't gonna help. Spending time trying to figure out who they are, how you can help them be better, how you can help them take over their schedule at some point is important.

But these are assets. You have assets that are out there to make you guys money, and they don't all work the same. Some of them need more oil. Some of them need more attention. Some of them like to run hard. Some of them like to run slower. Whatever the case is, these are people, and that's what separates us from AI, is these jobs are not gonna get replaced in a ton of years, or ever, because customers need people to climb on roofs.

They need advice. They need somebody to help explain why I should spend 35 to $150,000. What I give my sales reps, metrics that I think you guys should track, 'cause eventually it's gonna lead to, okay, we're missing the boat here, or we're missing the boat here.

Or, and reasons to praise them by tracking their numbers and understanding where their numbers are at. That means a lot to them, especially these Gen Z-ers. If you don't hold them accountable, it's not that you're holding them accountable, they just don't even feel like you're watching them. And that hurts.

And I've even been in those situations where like, dude, I busted my tail all month, and I have not heard from my sales manager one time. That sticks. Like, do you really wanna climb roofs for somebody that doesn't care about you? What I recommend, in the morning, uh, doing some file work immediately because it's just kinda top of mind.

I think sales reps can't rest, or they shouldn't rest until they know their customers or their files on Roofr are updated. Morning training, so doing some sort of training. So Kendo is a role-playing one. If you need a role-playing one that's out there that kicks, I think it's like 55 bucks a person. Doing role-playing, motivating them.

I have one sales rep I know that's newer. He just turned in 100 grand last week. He says once a week he likes to go to the area that's the hardest to even get an inspection. He says, "Because I like the practice of people saying no to me." And then he's like, "Then I go to the area for the other four days out of the week, and I crush it 'cause I got all my practice in even with my role-playing."

These people show up motivated. Midday organizing files, Roofr, et cetera, getting out in the field, and in the afternoon you know, they're out in the field for whatever amount of blocks that you guys have put in there. Again, putting it in their schedule. I usually do three to three and a half hour blocks that I say we're running hot.

You know, we're gonna be out there door knocking with a mission minimum," and, and you guys can have higher ones, but 500 doors knocked generally leads to five contracts is what I know. And there's spots where then you get better or you get referrals, and then it takes a lot less, right?

I'll just finish my wrap up so I can throw everything back to Pete. We are doing a giveaway today. The giveaway is a free insurance workflow structure. So this is one of the most detailed, I've I just haven't seen one more detailed for you to use to show your sales reps to understand, and maybe align it with your Roofr process.

And, there's a lot of you that might not even fully understand it, maybe that's a reason that you wanna talk with us. You can email me at dan@pe-assist.com. I'll throw it back to you, Pete  

Pete: Yeah, and when we're talking about, like, the first 90 days, I think a lot of times we operate under the assumption that if someone's coming in and they have previous roofing experience, that they're good to go.

We can just, like, turn them loose. And just because they have previous roofing experience does not mean that they're going to be successful in your roofing company, right? That's a major misconception that I've seen crash and burn multiple times, right? It's like, "Oh, this guy gets it.

I can just turn him loose and let him go. He'll figure it out." And, uh, the other thing I wanted to talk about, 'cause we're even talking about doing it with our customers at Roofr, is this idea of going beyond the 90 days to, like, an everboarding, right? Yes, we wanna make sure that, you know, in the first 90 days we're setting these people up for success, but are you potentially offering your people more training down the road, so that they can continue to learn, continue to advance?

I know Chris mentioned earlier, your manufacturers they're always hosting trainings, and certifications, and conferences, and stuff that you could potentially send your employees to learn more learn, you know, maybe new installs. For a while GAF was doing, like, solar.

I know a lot of the, commercial guys do a lot of trainings around install, and their materials, and things like that. And so, you know, are you allowing your people to continue to learn and continue to improve as employees? "Hey, we're gonna continue to coach you as you go on down the road here.

But yeah, man, I appreciate you guys coming on. This has been fantastic information.

Good interactions in the, in the chat. I think Joel threw your email as well, Dan, up in the chat there, so if anybody wants to grab that free free guide, they can. Or if you guys have questions for the team, feel free to to shoot Dan an, an email and they can answer any questions that you guys may think of after the fact.  

Chris: Well, thanks so much for having us, Pete and Joel.  

Pete: Absolutely.  

Chris: And everybody thank you for coming. And, if you can remember one thing from today, just stop trying to be hire heroes. Build systems that create them. Great contractors aren't built by one superstar salesperson.

They're built by repeatable recruiting, consistent coaching, clear accountability, and culture people actually wanna be a part of. And then the other contractors are built by PE Assist. They can't do that themselves. Just hire us.  

Pete: Thank you, everybody. Look forward to, seeing you guys all next time on the masterclass.

Thanks.  

Chris: Thanks, Pete. Bye, guys.

Published on
August 12, 2026
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