How to Build a High-Performing Sales Team in a Painting Business

Michael Murray: Hey everyone, welcome back to the Price Sell Paint podcast. I am Michael Murray, the owner of Textbook Painting. I'm joined as always by Jon Bryant, the owner of PaintScout. Today we have a special guest, Gavin Hepp, who is the owner of Webfoot Home Improvements and a sales coach with the Nolan Consulting Group. Gavin, welcome to the podcast. How are you doing?

Gavin Hepp: Real good this morning. Thanks for having me, guys.

Michael Murray: Absolutely. Jon and I have known you for a long time and we have a lot of respect for you and everything that you've done in the industry. We're excited for anyone that doesn't know Gavin to get some of the wisdom that Jon and I have been able to pick up over the years. Give us a little bit of your background — fill in some of the gaps and tell us a little more about who you are and what you're up to.

Gavin Hepp: We've had Webfoot Home Improvements, formerly Webfoot Painting, for 24 years now. It started when we were students in college — that was our first business. After college, we just decided we were going to do this and work to become the very best at it, and live in a place we enjoyed. We've just been at it ever since. I've always had a passion for sales. My first sales job was in second grade — door-to-door used sticker sales. That's a tough racket. But I was always finding things to sell through middle school and high school — gum, mistletoe around the holidays. I just always liked having a little something going. Always looking for angles.

Jon Bryant: Being from Eugene, Oregon, I imagine there are other things you could be selling, so good on you for keeping it above the bar. You guys are in Bend, Oregon now, and one of the things that has always impressed me is the size and scale of what you operate in what is seemingly a smaller area. Maybe you can explain a little about that desire to live where you wanted to live and then building a business there. How has that journey been?

Gavin Hepp: We grew up in the Portland area — big sprawling metropolis, huge population. But the suburbs of Portland really lacked any sort of culture. Strip malls, chain restaurants, all that. Central Oregon is three hours east of there. Bend is a little mountain town. When we moved there, it had about 90,000 people, and within about a three-hour driving radius, maybe 110,000 people. Beyond that, really nothing. So you're kind of on an island. But it's fairly affluent — people are moving there intentionally. Especially with COVID, a lot of remote workers and really nice folks coming up from California who keep us very busy. Small market, about 100,000 people within three hours, and our goal is around 11 or 12 million this year in 2026. It's not just painting anymore. We expanded to offer other services — complementary things where one feeds the next was always the idea. We've kept in touch with our customers and continued to provide useful services they needed, and managed to grow a pretty sizable company.

Jon Bryant: How many painting contractors are there in Bend, Oregon?

Gavin Hepp: A lot of small shops — hundreds. Maybe 400 or so when you count all the state licenses out there, though they all vary in how they operate.

Jon Bryant: Interesting. One of the things we've talked about is that there's only so much painting you can do, so in order to expand, you guys leaned into other services. How did you pick those services?

Gavin Hepp: We started with deck refinishing. We have a lot of wood decks out here and it was a service we were already kind of providing. We invested in equipment and processes — we even make our own cleaning products to keep costs down. We use planetary grinders with sanding heads instead of the typical sanders, which lets us really efficiently refinish decks. We do just under a million dollars in wood deck refinishing each year. That led to repairs — board replacement, siding replacement. We were reliant on subs and had some great ones, but not being able to control their schedule became too much of a challenge. So we had enough work to bring in in-house carpentry teams for repair work, board replacement, and siding replacement. We saw an opening there and said, we're going to do siding and deck building, not just repairs. Our first big project was a $300,000 HOA project for siding and deck replacement. Just like that, we were doing carpentry.

Jon Bryant: Love it. Digging into the sales side — to do 12 million, you've got to have a few people working with you. What does the sales team look like right now?

Gavin Hepp: Right now we have five sales reps and a sales manager. I previously operated as a director of revenue, but I've stepped out of that role and our general manager now oversees the sales department. Pretty much everybody sells everything, which is something I always wanted. For a while we had reps who were specializing, but ultimately I want a rep to be able to sell when the customer is ready to buy. Any break — like, "I have to bring Jeff out next week to look at this particular service" — was just a little obstacle we were creating. So we have a pretty lengthy training process. It takes about 12 to 18 months for someone to be fully up to speed and confidently selling all of our services.

Michael Murray: I'd love to hear more about that. Is the biggest challenge on the estimating side or more on the actual sales skills?

Gavin Hepp: The sales process does change depending on the service. We have some services that are want items — garage floor coatings, custom garage cabinets — versus things that are more maintenance-driven, like your house needing to be painted. The process can vary a little, but across most of our services it's pretty similar. The real challenge is understanding what's most important for each service, how we do it, and how to speak intelligently about it to give customers confidence. If you're selling against an owner-operator who's doing the work themselves, they can speak very intelligently about how to build a deck. Our reps need to be able to compete with that. So we start with one or two services, add the next once they have proficiency, then add the next. That's why it takes 12 to 18 months to get fully up to speed.

Michael Murray: How do you know when you've got the right person to keep investing in versus when you need to move on?

Gavin Hepp: That's the real challenge — you don't want to get nine months in and realize it's not a fit. I do 30, 60, 90 day milestones, and within that time, what I'm looking for is attitude and effort. Is this person trainable? Is this person worth investing in? That always buys them more time. Maybe their close rate or some other KPIs aren't up to par right out of the gate, but if they take feedback well and apply it well, that's someone worth investing in. When we're not seeing those things — they're sloppy with showing up on time, the same problems keep recurring, little details in proposals like punctuation and capitalization — you can know pretty quickly whether it's not going to be a fit. We try to listen to those signs and make changes before we're too heavily invested.

Michael Murray: What are some of the KPIs and benchmarks you look for — close percentage, number of quotes handled, things like that?

Gavin Hepp: Close rate is a big one, but more importantly, how many dollars are they closing? Are they actually hitting their target? We also look at VPS — Value Per Site, or what some call NSLI. It's how many dollars they're bringing in for every bid they go on. It's a combination of close rate and average job size. That's one we track really closely and benchmark across the board, and it varies by service. Those are the big ones.

Jon Bryant: Can you think of any examples of someone who hadn't shown the KPIs you wanted but turned it around? I'll be honest — my initial gut reaction has usually been right pretty early on. But I'm curious if you've seen a real turnaround.

Gavin Hepp: I certainly have, and I've also learned some lessons that have made me a little quicker to recognize when something isn't going to work. But I've been wrong a couple of times. In those cases, throughout the whole process there was a really great culture fit and values fit — they were teachable, took feedback well, participated in company trainings and events. All these green flags. The customer experience was going really well, proposals looked tight, project results were strong — I just needed more of them. That bought them more runway to learn. We have two reps right now who are absolutely crushing it. It took maybe two years before they really started, but now they're approaching two and a half million a year each, which I think is really strong for a sales rep.

Michael Murray: I'm hearing a lot about culture. It sounds like your sales team is pretty integrated with the entire team — not a lone wolf atmosphere. Taking a bit more time, but the end results can be pretty great.

Gavin Hepp: One hundred percent. They've put a lot of effort, especially in the last four or five years, toward building strong relationships with our production teams. A big part of that has been after action reviews — AARs — where sales and production get together regularly to talk about specific project types: what's working, what's not. That opportunity for honest, blameless feedback has built a really strong culture between sales and production. Sales makes mistakes, production can't always execute a project the way it was bid. Through those AARs, the team has become one team, which is a real challenge to accomplish. It's something we feel we've genuinely had success with.

Jon Bryant: For those unfamiliar, AAR stands for after action review — not pirate talk, though with your mustache, Gavin, it seems fitting. What exactly is an AAR?

Gavin Hepp: It's really direct feedback on how something went. Something they used in the military — what went well, what could we have done better, blameless feedback. When done consistently enough, you develop safety and comfort with feedback. To be able to tell someone "we should have done this differently" and have them own it — that takes time, practice, and modeling. Through repetition, these meetings become really valuable. Sales reps are saying, "I really missed that." A lot of people taking ownership of what they could have done differently, and supporting each other toward the goal of getting better. They don't have to be long — some are 30 to 45 minutes. We'll pull up a project that went really well, pull up one that didn't, and go through: what were our intended results, what were our actual results, what would we have done differently? Doing them regularly is what makes the difference.

Jon Bryant: Who's typically in that meeting?

Gavin Hepp: For something like exterior painting, it would be all our crew leaders, paint supervisors, someone from operations, all our sales reps and the sales manager. It might also include schedulers and resource coordinators.

Jon Bryant: I like that. Really productive idea. Michael, have you guys explored any of the AI ride-along tools for giving sales reps feedback?

Michael Murray: Gavin, have you looked at those at all?

Gavin Hepp: We've looked at them and priced them, but haven't pulled the trigger. I've had some friend companies that have played with them and I've been getting their feedback. There are some positives and some negatives, and I haven't heard enough to say we need it. But ride-alongs are so incredibly important — if you're not out there with your team, hearing what's being said and listening to what comes from the customer's mouth, you're missing so much. I see AI ride-along tools becoming more prevalent, and it'd be nice if the cost came down a bit. But in the absence of that, ride-alongs are essential.

Michael Murray: Talk more about that. Who's doing the ride-alongs, how frequently, how do you coach someone on it?

Gavin Hepp: If you have a sales manager dedicated to lifting up and training the team, I'd like to see them spending half their time out riding along with reps. That's where they provide the most value — not sitting at a desk crunching KPIs. Our sales manager at Webfoot has three ride-alongs per rep per quarter, which gets them about one a month. That's our minimum. When someone's close rate or VPS is dropping below targets, it's not just three — you've got to get out there as many times as it takes until you see results improve. The trap is when a rep is performing well and you stop riding along with them. A year goes by, something changes, they start doing things their own way, and you wonder why. No one has been investing in how they're doing — just happy with the results. We get complacent and stop doing the things that made us successful.

Michael Murray: What about role playing? Is that a big part of your success with the sales team?

Gavin Hepp: It's a newer focus for us, but I love role playing. When done well, it can be fun — it creates laughs, it's a vulnerable exercise that builds the team because it's a little silly and uncomfortable for everyone. We do a quarterly all-day training with the sales reps, each with its own agenda based on seasonality and what's coming next season. Every year we train on sales process and every year we train on price objections — it's built into our system. Part of that is two hours of role play where we just drill on things. We'll work on one specific word track, one little line, playing with inflection. Something like, "Had you considered what a project like this might cost?" — and just let them drill it 20 times until they feel comfortable. We also do longer role plays with a starting point and a finish line, trying to get to a budget conversation, and we'll rotate partners. It's been really impactful. We're doing it outside of sales too — with our resource coordinators, front desk, anyone who talks to customers for a living. You should practice talking.

Jon Bryant: So you've got role play and pirate cosplay going on over there — lots of play. That mustache is really bringing it all together. For those listeners who may not have a structured sales system, the idea of word tracks might be new. Can you run through that a bit more?

Gavin Hepp: A lot of people who don't have a structured sales process rely on things that come naturally to them — they're good at creating bond and rapport, they explain what they do well, they make the customer feel comfortable. That's a big part of selling. But the challenge comes when you start bringing on a sales rep. You can't just teach them what you do naturally — you need to teach them steps in a process, and then hopefully they layer in their natural skills. Without structure, it's just "watch me and do what I do," and that doesn't work. They need a roadmap. If you're in a position where you're bringing on a sales rep, first ask yourself: how do I sell? Break it down, put some structure to it. Nowadays you can even put it into ChatGPT — give me a Sandler sales process. Nobody should be without a sales process; they're so accessible now. The key is selling with structure. When you work a process consistently, you become very effective. You never skip the important steps, and those steps are designed to explore what's most important to your customers. If you're just freewheeling, you'll win with people similar to you, but not with everyone else. And freewheeling is tough to scale.

Jon Bryant: I'll share from my own experience — that transition from freewheeling to having a process was huge for me. Without a system, I started to hate sales. It put me in a bad place of "I'm not getting enough work, what do I have to do, maybe I have to be more aggressive" — aggressive about what? Having a process helped me better connect with customers, understand them, and help them buy. It changed my mindset completely. For anyone listening who doesn't have a system, go to ChatGPT and get one. Sandler is great. And if you're struggling as a sales rep, go back to your system and ask what you're not doing. Every time something goes wrong, if you go back to the system, you can re-center yourself — you've probably just gone off course. Would you guys agree?

Michael Murray: A hundred percent. And that's where having a sales manager or sales coach comes in — going back to the ride-alongs. Without a system, you can't drift away from it, but you also have nothing to return to. The best athletes and best business executives spend a lot of money on outside coaching for good reason. Gavin, you're now doing sales coaching with companies outside of Webfoot through Nolan Consulting. What does that relationship look like?

Gavin Hepp: Being outside someone's business means all I have visibility to is that sales rep — their skills and what they need to be successful. I'm not distracted by how a project went last week or what's going on in their office. It's structured, dedicated, focused time just talking about them and their process. Like you said, the best athletes and business leaders all have coaches and mentors — someone to help pick them up, help them prioritize, help them realign. That's really what you're trying to do: catch them, refocus them, ask good questions, get them to open up, and help them find the answers as much as possible.

Jon Bryant: Where do you start when you come into a new coaching relationship?

Gavin Hepp: You're trying to figure out who you're working with. There are some great assessments out there — DISC is a well-known one. What makes them tick? What motivates and drives them? That's really important, and it also helps spotlight where the challenges are going to be. For example, if someone has a really low I on DISC, they may not have the emotional intelligence of someone with a high I, and things you explain don't always click for them. They might not understand why it's important for a customer to feel safe and comfortable, or why you set the table at the beginning. They just want to get right to it. We're all wired differently. Once I understand who I'm working with, we can decide where attention and time needs to be spent. For someone with really low I, I spend a lot more time explaining the importance of that emotional connection. You don't have to feel it, but you have to understand it — because it's real for your customers.

Michael Murray: You mentioned "setting the table" — Jon and I know what you mean, but can you explain that for someone who might not?

Gavin Hepp: Setting the table is your first five to ten minutes when you arrive at a project. It's the most important part of any sales process, regardless of what you're selling. This is where you set expectations for how you're going to spend your time. When we arrive at someone's home, they're unsure what's going to happen — they're a bit anxious and uncomfortable. We have the opportunity in those first few minutes to catch them and say, "Hey, would it be all right if I just spend a couple of minutes talking about how we're going to spend our time today?" And they'll say, "Yeah, sure." Then you walk them through it: "I'm going to have some questions for you — is it okay if I shoot some your way?" We just got our first yes of the day. Then: "We'll tour the house together — I really want to see what's important to you and the scope of work." And then, when the table is set really well, you say: "At some point after I'm done with my measurements, I hope you feel comfortable enough to have a conversation about what this all costs." They'll say, "Yeah, that makes sense." I've now teed up the budget conversation. And: "I'll have a price ready for you before I leave. If you're not ready to make a decision today, let's just set up a time in the next few days to touch base and go over any remaining questions." I'm teeing up that next step agreement. So when it comes time to say, "It sounds like you're not quite ready today" — they already expected it. It goes smoother. You get more access to budget information because they know it's coming. You told them you'd talk about money, so now you are.

Michael Murray: You're also positioning yourself as an expert. The homeowner instantly has confidence and credibility in you. That's what homeowners are hoping for, especially in the upper price point — someone who knows what they're doing and is going to take care of them.

Gavin Hepp: Exactly. They're looking for competence. They want to feel taken care of, want things to go smoothly, want someone looking out for things they might not have noticed. When they feel comfortable and safe, they ask better questions, they're more engaged, they like and trust you more — and you get more closes at higher prices. Everything goes smoother. When reps are having a hard time selling, I always go back to setting the table. If you can't get customers to call you back, are you teeing up that next step agreement? When you follow up on something they're already expecting, you get more of them.

Jon Bryant: I once experienced the opposite firsthand. I was at an estimate for a large 5,000 square foot home — walls, trim, ceilings, moving-in job. I'd just set the table and started touring the house when another contractor showed up an hour early. He came in, said "Hey, how's it going? How many square feet?" Customer said 5,000. He said "Perfect, I'll send you an estimate Tuesday" — and left. I followed up with the customer afterward, just curious: "How did that feel compared to what we did?" They said, "That guy's not getting the job." I asked why. They said, "He doesn't know anything about my life, my project, what I want. He just showed up and 5,000 square feet was enough." That customer didn't want cheap — they wanted to know their home was in good hands and that they had someone to call after. These things really matter.

Gavin Hepp: There are a lot of folks who operate that way — show up, pepper questions, your guard goes up because they haven't set the stage. We love bidding against those folks.

Michael Murray: Sounds like a shameless plug moment — if you know someone like that, share the Price Sell Paint podcast and help a friend out. Gavin, while we're on the topic of competition — you're in a market of about 100,000 people. How do you think about competition? Scarcity mindset, abundance mindset? Are you watching their pricing?

Gavin Hepp: I believe no one delivers a service like we do — I have great confidence in that. There have always been people with lower prices than ours, and you can probably find someone half our price. We try not to worry too much about that. We have production rates, we know how long projects take, so we have great confidence in our pricing. As the established player, we can say we've been here for 25 years and have homes we painted that are just coming up on their second job after 12 years. That's nice to lean on. But competition has gotten trickier — someone starting a painting company today has tools and technology that let them look like a pro pretty quickly. We try not to put too much weight behind it and stick to what we know and our strengths. We don't let competition affect or influence how we sell.

Michael Murray: One of the best things I've heard on that topic: if a customer says, "I got a price that's half of yours, why is yours so much higher?" — just reframe it: "Why is theirs so much lower?" You said you have the right price. That frame of mind is so important in our industry.

Gavin Hepp: We deal with that a lot and do a lot of role playing on it. Sometimes you just repeat back the last three words: "Half your price... I wonder what they missed." Or, "That's really surprising — we never hear that, so I'm a bit confused by that. Without looking at their proposal I can't say why they'd be half our price, outside of doing half the work. We're all working from the same labor pool around here. Labor doesn't vary tremendously, and we're getting materials from the same place. It really comes down to how many hours were put into your project. To do half the price, you've got to do half the work."

Michael Murray: Or be half as good.

Jon Bryant: Over the years I've found that question really falls apart for the cheap guys when you actually ask the customer how they got to that price, and the customer says, "I don't know, they just kind of came up with it." Well, maybe ask them how they came up with it — because they just crumble. Meanwhile we can answer it confidently. You've been in business 25 years, you know how long things take. It comes back to: what are you looking for? Because maybe you want that half-price job, but that's not what you told me when we talked. It reopens that conversation.

Gavin Hepp: We'll call back to our takeoffs — I know exactly how many linear feet of fascia you have, I have 17.2 hours in for scraping the fascia on the front side of your house. Ask them how much prep time they have for that same fascia. Thanks to the fine work at PaintScout, we can display those finer details.

Michael Murray: Woo! Choosy homeowners choose contractors that use PaintScout — that should be the new slogan.

Jon Bryant: It gives you confidence to address that question. I see it online all the time — people asking "what's the price per square foot in Wisconsin?" And it's like, well, how long does it take you? Once you get to that level, your sales team feels more confident because there's an actual reason for your price. They won't crumble in that conversation. Do you guys feel the same?

Gavin Hepp: Without question.

Michael Murray: I don't know how you could hire sales people in this industry without some sort of framework. You can do it on pen and paper — that's how we started — but I can't imagine asking a homeowner "how many square feet is your house?" and then saying "I'll get right back to you." The homeowner just thinks you're making it up based on how big the house is or how nice their car is.

Gavin Hepp: That's a lot of new construction. It's like, interior is a buck a foot, exterior is two bucks a foot. It's kind of crazy how that estimate works, but that's new construction pricing for you.

Jon Bryant: I still get confused by it. I think the builder looks at it as a percentage of home value — the house is $100,000, so 4% goes to painting, you get $4,000, figure out your square footage number from there. Whatever that dollar-per-foot figure works out to, people have just been throwing it around forever. Did you guys know why that is? Why contractors still quote in square foot dollars?

Gavin Hepp: It's treated more like a commodity — this is what you can get in this market for this type of service. That's honestly one of the reasons we got out of new construction entirely years ago. It was always, "This one's a little different for these reasons, there's extra masking here and there." And the response was, "We'll catch you up on the next one." No thanks.

Michael Murray: Yeah, even new construction is really hard to be profitable in. And that square footage mentality is just tribal knowledge — I worked at a painting company, I think this is how they did it, I asked at the paint store. It just gets passed on and nobody stops to ask whether there's a better way or whether this is how the best contractors in the industry are actually doing it. Spoiler: it's not.

Gavin Hepp: And to be scalable, you need something trainable, something systematic. If it's just you, fine — you can eyeball a house and know it's going to be 15 grand. But when you bring someone else in, they don't have your experience. They don't notice the railings that you know are going to cost more. You need a system — not just for sales, but for estimating.

Michael Murray: And then that business owner says, "I can't hire anyone good, there's no one out there, I can't delegate this." With no inward reflection on what they're doing to make this a job someone could actually learn.

Jon Bryant: Well, maybe we can end it there. Gavin, this has been fantastic as always. For anyone interested in sales coaching, Gavin is available through the Nolan Consulting Group — check it out. We all need coaching. Gavin, thanks for your time — always a pleasure.

Michael Murray: Thanks, Gavin. Good to see you.

Gavin Hepp: You guys are great. Thanks for having me. Appreciate you.

Jon Bryant: And with that, if you appreciate the podcast, give it a like and a subscribe. We'll see you in a couple of weeks with another great guest. Thanks everyone — have a great day.

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