PCA Articles

When the market cools off, painting contractors feel it fast. Referrals slow down, ad costs creep up, and it takes more estimates to land the same amount of work.

It’s easy to blame the economy. But a slow season usually exposes something else: a sales and marketing process that was running on momentum instead of a system.

In a recent Breakthrough Academy Contractor Roundtable, I sat down with three painting business owners: Joe Kelly of JK Paint, Mason Marquis of SprayTex Painting, and Toby Woodiwiss of Woodiwiss Painting. CompanyCam Founder Luke Hansen joined them to talk about how technology is changing the way contractors market their work.

All three painters have built multimillion-dollar companies. None of them got there by outspending the competition on ads. They got there by taking control of their pipeline, their conversion rates, and their sales teams.

Here are five shifts they’ve made that any painting contractor can start using this season.

1. Track What Happens to Every Lead, Not Just How Many Come In
A full inbox feels good. But a hundred leads a month means nothing if half of them are tire kickers, your estimators can’t get in the door, or your close rate is stuck.

Joe Kelly learned this as JK Paint scaled. His team now follows every lead source all the way through: appointments set, jobs booked, and revenue produced. That shows him which channels actually pay for themselves.

Toby Woodiwiss takes it one step further. After every estimate, his sales reps rate the appointment from one to five. Over time, that score reveals which channels bring in homeowners who value quality work and which ones bring in price shoppers.

If you want the same clarity, start tracking these numbers by lead source:

• Lead volume and lead quality
• Cost per booked appointment
• Lead-to-sale conversion rate
• Closing rate
• Revenue compared to marketing spend

Once you can see them side by side, it gets obvious where your money is working and where it’s leaking.

2. Build a Marketing Plan That Holds Up in the Slow Season
Every painter knows the winter dip is coming. The companies that ride it out best don’t wait for the phone to ring.

Danny Kerr recommends balancing passive marketing (ads, your website, search engine optimization and AI search) with active marketing your team can dial up or down as needed. Think outbound calls, reaching out to past customers, business development, door knocking, and asking for referrals.

Joe Kelly’s team starts planning for the off-season in August. They ramp up outreach, roll out winter promotions, and set weekly targets for things like flyer drops and yard signs. The result: all 10 of his crews stayed busy through the winter.

Mason Marquis uses seasonal promotions at SprayTex Painting to nudge homeowners toward bigger interior projects during the slower months. Interiors are a natural fit when exterior work dries up.

The takeaway is simple. A year-round plan with clear weekly activity goals gives you something steadier than hoping the referrals keep coming.

3. Fix Your Sales Process Before You Spend More on Ads
Before you raise your ad budget, look at what’s happening to the leads you already have. Ask yourself three questions: Are we qualifying homeowners before we book the estimate? Are we presenting the price in person? Is our lead follow-up consistent?

Here’s where the panel sees the biggest wins for painting contractors.

Qualify before you drive out. A short screening call keeps your estimators in front of good-fit homeowners instead of burning half a day on someone collecting five bids.

Present the estimate on the spot. Joe and Toby both push for this. When your rep presents in person, they can answer questions, handle objections, and ask for the job while the homeowner is still picturing the finished room.

Make your sales process repeatable. Toby’s team uses structured training, role-playing, and self-evaluations. That keeps every rep running the same play and makes it easy to spot where someone needs coaching.

Follow up with value, not pressure. Instead of asking “Are you ready yet?” send something useful: color ideas, photos of a similar project, or a recommendation. Joe points out that a paint job competes with a lot of other priorities in a homeowner’s life. A quiet prospect isn’t always a lost one.

4. Turn the Work You Already Do Into Marketing
Most painting contractors are sitting on their best marketing asset and don’t use it: the work itself. Before-and-after shots, jobsite photos, and customer conversations are exactly what future homeowners want to see.

Luke Hansen shared how CompanyCam is building tools that turn jobsite photos into social videos, Google Business Profile posts, and online project portfolios. Your crews are already taking those photos. Now they can pull double duty without anyone sitting down to “create content.”

Danny Kerr also talked about AI meeting recorders that capture sales conversations. They help you coach reps, and they surface the questions homeowners ask most. Those questions are gold for your website, your ads, and your social posts, because they come from real customers instead of guesswork.

The point isn’t to automate for the sake of it. It’s to use what’s already happening in your business to make your marketing more relevant and your sales more effective.

5. Build a Sales Team That Wins on More Than a Script
Most sales training focuses on objection handling, discovery questions, and closing. Those matter. But Mason Marquis believes emotional awareness matters just as much.

At SprayTex Painting, Mason hires salespeople who are self-aware, hungry to improve, and able to build real connections with homeowners. He even works with an in-house counselor to help his team build people skills and understand how they react under pressure.

Toby Woodiwiss takes a more process-driven approach with structured training, role-playing, self-evaluations, and weekly accountability meetings.

Different styles, same foundation. Both hire for self-awareness and coachability. Both train consistently, review performance weekly, and track sales activity against clear goals.

If your results swing from rep to rep, you may not need new salespeople. You may need a better system for developing the ones you have.

The Bottom Line: You Can’t Scale What You Can’t See
The most successful painting contractors don’t leave their pipeline to chance. They know where their leads come from, they track their numbers, they develop their salespeople, and they market on purpose, even when it’s slow.

When the market shifts, they don’t just work harder. They adjust the system.

You don’t have to fix everything at once. Pick one bottleneck, whether that’s lead quality, follow-up, or a missing off-season plan, and build a simple process around it. Then move on to the next one.

About Danny Kerr
Danny is one of North America’s top contracting thought leaders and a well-loved industry speaker, helping thousands of humble, hungry, smart contractors reclaim their time, profit, and lifestyle. His entrepreneurial journey began in his teens when he started a painting company as he got his life on track following a tumultuous upbringing. Since 2015, along with partners, he’s built Breakthrough Academy (BTA) into the foremost industry expert on operational systems implementation for contractors.