How $10M Contractors Keep Crews Busy All Winter (Roundtable)

Winter doesn't have to mean empty calendars, layoffs and scrambling to keep your contracting business afloat.

While many contractors accept the slower season as inevitable, others are finding ways to keep their crews working, protect their margins and build momentum for the year ahead.

So, what's their secret?

In this episode of Contractor Evolution, Breakthrough Academy's Danny Kerr sits down with three successful painting contractors: Joe Kelly of JK Paint, Mason Marquis of Spraytex Painting and Toby Woodiwiss of Woodiwiss Painting, alongside CompanyCam founder Luke Hansen.

Together, they break down the sales, marketing and operational strategies helping them generate consistent work, even when demand slows.

5 Ways Successful Contractors Keep Their Crews Busy Year-Round

Keeping your pipeline full during the off-season takes more than offering winter discounts. These contractors share five strategies that help them stay ahead.

1. Plan for winter before it arrives. Waiting until business slows to start marketing puts you on the defensive. Joe Kelly starts planning his winter strategy in August, giving his team time to generate demand before the seasonal slowdown hits.

2. Track the numbers that actually drive revenue. More leads don't necessarily mean more jobs. Monitor booked appointments, lead quality, closing rates and cost per appointment to identify gaps early and make smarter marketing decisions.

3. Make winter promotions work for your margins. Discounting doesn't have to mean sacrificing profitability. Mason Marquis explains how strategic winter offers, larger projects and flexible scheduling can help keep crews productive while protecting gross profit.

4. Take control of your lead generation. Don't rely entirely on referrals or paid advertising. Combine passive marketing with proactive outreach, including reconnecting with past customers, asking for referrals and neighborhood marketing campaigns.

5. Get more sales from the leads you already have. Generating more leads isn't always the answer. Improve your sales process by qualifying prospects, presenting estimates on-site, following up consistently and coaching your sales team to build stronger customer relationships.

Turn Your Slow Season Into a Competitive Advantage

One thing becomes clear throughout the conversation: keeping crews busy year-round isn't just about finding more work. It's about building systems that create predictable revenue.

From tracking sales performance to getting your entire team behind your winter strategy, these contractors show what's possible when you stop reacting to seasonality and start planning for it.

And the benefits go beyond surviving winter. Consistent work helps you retain good people, maintain momentum and enter your busiest season ready to grow.

There’s more in this episode! You’ll hear how these contractors approach winter marketing, manage their sales teams and turn seasonal challenges into opportunities when you watch the full episode.

Ready to build a more predictable, profitable contracting business? Book a complimentary discovery call with Breakthrough Academy to explore how better systems and strategies can help you grow year-round.