The Future of Painting Sales: What Contractors Need to Know // Danny Kerr

Jon Bryant: Hey everybody, welcome back to the Price Sell Paint Podcast. I’m Jon, here today with Danny Kerr from Breakthrough Academy. Super excited to have you, Danny. Michael’s not here because he has better things to do — I’ll be writing some nasty things about him in my journal tonight. Danny, welcome to the podcast. For those who don’t know Breakthrough Academy, fill us in.

Danny Kerr: Thanks for having me, Jon. We started in the franchising space for painting — my business partners and I were essentially College Pro Painters back in the day. Personally, I was trying to figure out how to be successful in life at eighteen, nineteen, twenty. Beyond that, I was also trying to not end up like my dad, who was a drug addict. College Pro kind of lifted me out of that world. It introduced me to a peer group of motivated, driven people my age who were doing everything it took to hit a goal. I spent eight years with them — went from franchisee to GM to VP of Western Canada for recruitment and development. I couldn’t imagine doing anything else.

Along the way, our CEO challenged us to think about what businesses we could spin off from College Pro. They came up with lawn care, gutter cleaning, more things with students on ladders. I honestly pushed back on that — I thought we had enough risk there. What I felt we were truly world-class at was teaching young people how to run these businesses from soup to nuts, getting them operationally ready and making real money. There’s a gift in that process that could be shared with the world.

That was the original idea for BTA — a pitch at an internal Dragon’s Den event. When I left, I thought: my entire life changed because of entrepreneurship in a community of other entrepreneurs. And no one is offering that franchise-level process and support to independent contractors who are out there alone with no direction. That’s how it came to be. We’ve been at it eleven years now, and the fundamental concept is still that experience I had when I was younger — how do I bring that to other people?

Jon Bryant: And you work with painting contractors as well as other trades?

Danny Kerr: Yes. Painting is where it started, but the contracting space generally has three types: large average job size, mid average job size — where painting lives — and small average job size. They have slightly different production and sales cycles, but the processes are similar. We’ve separated those three legs into distinct tracks in our program — a builder track, a service track, and so on. Painting is a core part of it.

Jon Bryant: And the team at Breakthrough — did everyone come out of the College Pro experience?

Danny Kerr: Early days, a large majority did. I used to call it the College Pro After Party — we all grew up, went into corporate jobs, and I said, “Guys, can we just keep hanging out and call it BTA?” Now it’s obviously expanded. We have about 50 staff total, 20 of whom are coaches. We select coaches for specific industry types — construction, mid-average job size, service. What we look for is: have you run a business? Have you been a COO or operations manager in a large organization? Do you have that boots-on-the-ground experience? And do you have that coaching bone in you?

Jon Bryant: You guys still think contracting will be around in five years?

Danny Kerr: For five years, yes. It’s actually interesting watching what’s happening with private equity, AI, and eventually robotics — painting does lend itself to automation over time. But if anything, there’s more opportunity in this marketplace than in most. We’re one of the least disrupted industries from a labor standpoint, and there’s a ton of upside in utilizing the tools and capital coming into the market.

Jon Bryant: That’s lucky for you — I’ve heard SaaS is dead.

Danny Kerr: It’s a scary place to be in SaaS right now. There seem to be two sides: those benefiting significantly and those going obsolete overnight. It’s a razor’s edge. For our industry though, I think what we need to evolve is our process, how we offer what we offer, and how streamlined we are. My partner Igor and I talk about this idea that everyone now expects an Amazon-level experience. If we’re not rising to create that for our customers, we’ll lose market position. Customers don’t want to research a bunch of companies, get multiple quotes, sit through multiple estimates, and pick someone. They want it at their fingertips — accurate and ready to go.

Jon Bryant: That’s a great segue into “Mastering Sales in a Digital Age,” which is a session you’re putting on that we’re part of. For those listening, we’ll put a link in the description. What does that mean to you?

Danny Kerr: It’s about marrying what has always worked — Google ads, door-to-door marketing, signs and flyers, relationship building — with how we use technology to make that experience more streamlined, better for the customer, and better ROI for the organization. We have tech on our side in a way we’ve never had before. The goal is to take those grassroots strategies and equip ourselves with the tools to be superhuman about it.

Jon Bryant: When you describe the Amazon experience, what does that look like in the future of contracting specifically?

Danny Kerr: I’m a homeowner, so I can speak to it. I just got my roof done. Some contractors came in with a quick ballpark number and emailed me two weeks later. Terrible experience — I didn’t understand the value of what I was spending $37,000 on. The better experience would have been documentation of our conversation transcribed in real time, a same-day or on-site quote so I could make a decision, clear features and benefits, digital payment, automatic invoicing, reminder sequences, a way to click and pick my colors, expectations set throughout the production process. Creating that full customer journey with technology at every stage — that’s the opportunity. And each piece of it can be innovated on in a way that brings real value to the customer, streamlines your sales process, helps you close more deals, and sets you apart from the competition.

Jon Bryant: How many quotes did you get for the roof?

Danny Kerr: Two. One was from a friend who’s brand new in business, and one was from one of our members who is well established. Our member was significantly higher — they have more overhead and I’ve trained them well to charge properly. But interestingly, I went with the more expensive one. The sales experience told me what the production experience would be. And one of the deciding factors was simple: both sent me quotes, one on paper and one digital. I called both with questions. One got back to me within the day, the other within a week. That was it. I was out. I paid an extra $8,000 for our member to do the work.

Jon Bryant: That’s so interesting. I think a lot of contractors haven’t been in the position of spending $37,000 on their own home. Getting into your customer’s shoes — understanding what the experience is actually communicating — is huge. But not very often do I hear contractors say “our process needs to get better.” They tend to blame the customer instead.

Danny Kerr: Looking within and understanding that is everything. Those sound bites you just described — quick communication, how your estimate appears, the value you deliver throughout the sales process — it all says something. And a lot of people don’t take personal ownership of the problem.

Jon Bryant: So where did you take them from, and how did you get that member to the point where they could close you at a higher price?

Danny Kerr: They were doing about $3 million when we met, doing a lot of the work themselves, not very profitable, charging far less than they should have, and actually losing money pretty well when we first engaged. Cash flow was so tight they were running into debt. We had to do a few things: first, build the right team around them so it wasn’t all on them, and make that team profitable while also bringing in more work. They had the mindset that if you’re good and cheap, everyone will choose you. We redeveloped that. We also fixed their deposit structure — they weren’t collecting enough upfront to cover material and labor costs. Got their financial metrics dialed in. I think they’re at about $12 million now — more than tripled, maybe quadrupled. Good cash flow, good margins, clear understanding of their numbers, and a strong team around them.

Jon Bryant: Did you change anything in their sales process — bring in more digital tools?

Danny Kerr: Not in the sales process specifically, but they did come to me after I was their customer and asked for honest feedback. Which I loved — I hope they do that with everyone. The main feedback I had was around the end of the project. The subs had finished, one crew leader checked in quickly, I gave a couple notes on cleanup, and they said someone would come back in a couple weeks for a final walkthrough. But I had no clarity on who, when, or what that meant. I called them somewhat upset about granules from the roof covering my patio. A guy came, fixed it, everything was fine — but the communication around that wrap-up process just wasn’t defined yet. The sales process was smooth, production was generally fine, but that post-production experience felt rough. And that last impression matters — for getting paid faster, for getting the right review, and for how they made me feel.

Jon Bryant: The last five percent is hypercritical.

Danny Kerr: Huge in painting. If you produce a job without completing touch-ups, move your crew off site, and then take a week or two to come back — the customer is sitting there frustrated, your cash flow is stalled because you haven’t collected final payment, and now your crews are all busy on other jobs. That wrap-up process is massive and simple if done right. But without accountability around it, it’s very easy to leave four or five jobs unfinished and unpaid.

Jon Bryant: What do you think becomes standard in the sales experience over the next three to five years?

Danny Kerr: The ability to provide a digital quote or even a click-to-buy experience before you ever get there is coming. I’ve actually seen this in roofing already — the owner of Sumo Quote is building a process where you can get a quote, click to buy, and have a roofing crew show up on a scheduled date without ever meeting anyone. All subcontractor-based, scalable across North America with no local infrastructure. I think that’s coming for painting pretty quickly. With Google Street View and top-down satellite imagery, you can start to incorporate a lot of this into quotes. There’s always nuance — especially for interior work — but I don’t think it’s going to be that hard to figure out.

Jon Bryant: Interesting. I’ve seen some challenges with virtual sales at certain dollar ranges. PaintZen did something like this around 2010 — a click-to-purchase widget for New York condos where you’d enter the details and buy. But eventually every path ended in a sales appointment anyway because people wouldn’t commit without one. PPG acquired them for an exorbitant amount and then found that nobody wanted to use it without the human element.

Danny Kerr: That doesn’t surprise me. The human relationship matters. But Elon Musk has a point — we are the most stubborn point of change management that will ever happen. The most streamlined option does eventually take over. How long that takes, I don’t know. I’m a huge proponent of human relationship, so I hope it remains central. But we’re not going in the direction of more manual and more hands-on. We’re streamlining. The sales relationship might be one of the last things to go — but we’ll see.

Jon Bryant: During COVID there was a lot of virtual estimating going on. Win rates were atrocious — around 10%. You could do all the work, but the relationship piece was missing. I think there’s a gap between the future we imagine — click, quote, done — and the reality that it takes one person getting screwed over before the whole thing falls apart.

Danny Kerr: And that’s on everybody’s brain right now because AI is changing everything. Your entire customer journey needs to be rethought, and you need to discover as you go what level needs human interaction and what level can be automated. At BTA, I’ve been looking at AI agents for inbound and outbound. What I’ve heard pretty unanimously across our members: for inbound, it works well — people are happy that someone picked up and routed them. For outbound, you’re annoying people. That’s a simple but important nuance. Trial it, let it fail a little, and pivot. I do believe the human relationship will become one of the most valuable things a company can offer — it may end up being the rarest commodity. But our job as entrepreneurs is to understand what’s coming, test it, and redefine the process. If we stick to the manual way, competitors will come in and take our lunch.

Jon Bryant: I saw a graph the other day showing what AI will replace — sales was one of the last things, because it’s truly relationship-based. The further we go into AI, the more people will probably crave personal interaction as a pushback. All the cool kids are apparently carrying Discmans again.

Danny Kerr: Totally saturated in technology, so we go analog. That tracks.

Jon Bryant: Let’s shift to sales teams — building and training them. Our audience is sales reps and business owners. Where do you start?

Danny Kerr: First, understand the sales process so you can hire around it. You need someone to open the door, someone to close the door, and someone to keep everything organized on the back end. Early in business, that’s usually one person doing all three. But as you grow, you can actually create three separate roles that pass the ball strategically.

Openers love to build relationships, love to get to know people — but they’re not great closers because they don’t want to damage the relationship by asking for the sale. Those are your outreach reps, your follow-up people, your booth relationship builders. Closers — your estimators — are willing to ask for the sale, ask the hard questions, challenge objections. Slightly different personality. And both openers and closers, because they’re so relationship-oriented, tend to struggle with details and back-end admin. Give them even part-time admin support, and instead of spending 10 hours a week on things they’re bad at, they can go do more of what they’re great at.

Jon Bryant: How do you know who’s who — what to look for in each type?

Danny Kerr: DISC profiles are a quick, simple starting point. A closer is usually more of a D — dominant. An opener is usually more of an I — interpersonal. Admin support is more of a C — compliance-oriented. Broad strokes, but useful as a screening layer.

When it comes to interviewing specifically, there’s one trait people often overlook for outreach roles: what I call “fundamental” — the ability to handle stress in pursuit of a goal. Outreach is one of the highest-turnover roles in any company. People doing 100 calls a day, getting rejected constantly. What determines success isn’t just sales ability — it’s emotional resilience. Not tenacity, not hard work resilience — specifically the ability to go through the highs and lows of rejection all day long and come out steady. No fight or flight dominance, just a quiet, consistent forward motion.

To interview for it, I look at past experience and ask: what’s the hardest experience you’ve ever been through? What were your goals along the way? What I’m watching for is someone who goes through the highs and lows quickly and comes out learning something, without destroying everything else they had going on. Goals stayed consistent, they remained steady. That predicts a more stable, consistent sales rep rather than someone who’s on top of the world one month and ready to quit the next.

Jon Bryant: And how do you get past the general platitudes salespeople are good at in interviews?

Danny Kerr: You get to the story. I had a head of sales candidate recently whose resume blew me away. But he was speaking entirely in generalities. I asked him what he looks for when interviewing a sales rep — he gave good, polished answers. Then I asked how he actually finds those traits in an interview. He had nothing. No substance behind the knowledge. So I went deeper: what specifically happened? What happened on Tuesday? Who was involved? What happened next? What did you learn? Specifics get you past the fluff.

Jon Bryant: I always used to ask people to tell me about the last event they planned. Nothing to do with the role, but you can ask so many follow-up questions. How far in advance did you notify people? What method did you use? How many showed up? How did it go? It’s really hard to fake generalities when someone’s asking you for specific details.

Danny Kerr: Exactly — get to the story. I picture the person as a stick figure on a white background. As I talk to them, I need to add detail until I have an HD picture of exactly who they are and what their world looks like. That’s when you really understand whether the trait is there or not.

One thing I’ve found after years of hiring: I kept all my interview notes. A year later I’d go back and read notes on someone who didn’t work out, and it was all right there. They’d told me exactly who they were — and then sold me out of believing it. Past performance predicts future results. If you can get to that level of detail in an interview, try turning off their name and putting your name, turning off their old company and putting yours. Ask yourself: am I okay with this playing out the same way here?

Jon Bryant: For business owners listening — getting that first sales rep is a huge milestone. There’s a decision point though: do I do the sales or do the operations? What do you see most often?

Danny Kerr: Here’s the order that 99% of people should follow. First, hire admin help. Doesn’t have to be full-time — remote, part-time, a student — but get help with your administrative work. It’s the cheapest ROI for the most time-consuming low-skill tasks you have. Second, hire for production management. The owner is almost always the best salesperson — most passionate, most knowledgeable, and removing that sales engine can remove the heartbeat of the business. There are cases where someone is wired for production and genuinely bad at sales, and in those instances maybe sales comes first — but it’s a risky move when the business is small because it can tank your profitability. Almost always: admin first, production management second, sales third.

Jon Bryant: Let’s end with some objection handling. Walk us through your approach.

Danny Kerr: The biggest mistake people make is jumping into defend-and-explain mode the moment an objection lands. That puts the customer on the other side of the tennis court. You want to be on the same side. The most important step is having an open-ended response ready that engages the conversation further without defending. So instead of “let me explain why our price is justified,” you say something like, “Thanks for telling me that — genuinely appreciate you being upfront. What are some of the things you guys need to think through between now and then?” You’re asking for more explanation, not a yes or no.

To make this automatic, we’d put the ten most common objections on flashcards — objection on the front, open-ended response on the back. You have to get all ten in a row cleanly before your brain defaults to defend-and-explain. Drill it until the response is automatic.

From there, you keep asking questions until you get to the real story behind the objection. It’s almost never the surface-level answer. Someone says they need more time — the real story might be that they got burned last year not getting multiple quotes and promised their spouse they’d never do that again. Now you understand what you’re actually solving for.

Once you understand the story, your job is to problem-solve — not to convince them to buy today, but to provide a logical solution that helps them make a better decision. Maybe you let them get other quotes but provide referrals and hold a specific follow-up date. Maybe you clarify that the price won’t change so there’s no risk in waiting. Whatever it is, you’re working through it with them, not just letting it float. And then — you re-ask for the job. Once you’ve solved the objection: “Does that help? Do you feel like we could go ahead today?” If they object again, you can go through the circle again — once, maybe twice. Read the room. If it’s feeling forced, stop. But if the rapport is strong and you’re genuinely trying to help, you can do it a couple of times.

Jon Bryant: Don’t leave without a decision.

Danny Kerr: Exactly — or at minimum a clear next step with a task and a date attached to it.

Jon Bryant: Danny, this has been really fun and genuinely valuable. For those who want to connect with you and Breakthrough, where do they go?

Danny Kerr: I’ll put a link in the show notes with a free hiring package — covers building your ideal candidate profile, better interview questions, and a clearer process for identifying the right people for your sales team. Inside that, you can also opt in to connect with us directly. We also have a podcast called Contractor Revolution if you want to listen on the road. And our website is btacademy.com for everything else.

Jon Bryant: Love it. Danny, thank you so much. Guys, thanks for listening — like and subscribe as always, and we’ll see you next time on Price Sell Paint.

Danny Kerr: Awesome. Thanks, Jon.