De-Seasonalizing Your Business for Stability and Profit

Most contractors are their own worst enemy when it comes to pricing. That was the sentiment from John Conway, Chief Operating Officer at Redwood Services when he talked with us during an episode of Toolbox for the Trades. 

The fear of charging what they're worth doesn't come from customers—it comes from within.

"Most of the people that are scared of the price are us, the contractors and the service companies," Conway. "Most customers want great service delivered by a great technician using superior parts and services, and they're willing to pay for it."

Conway learned this lesson early in his career when he reluctantly joined his father's one-truck HVAC operation in Memphis. What started as a temporary gig to avoid traveling became a 30-year journey that taught him the fundamentals of building sustainable service businesses.

After selling his own company and coaching over 100 contractors nationwide through Nexstar, Conway now partners with Redwood Services to help trades businesses break free from seasonal dependency.

The key isn't just surviving the slow months, it's thriving year-round.

Conway's approach centers on strategic planning rather than reactive scrambling. February happens every year, yet many contractors act surprised when demand drops.

"There's this thing called February and it's gonna happen every year," he says. "Sometimes we go into February and we go, oh, it's really slow. Like we didn't know February happened."

The solution requires multiple strategies working in harmony: adding complementary trades, leveraging aged equipment data, building robust membership programs, and most importantly, treating your team as your greatest asset.

"You show me a business with a bad culture. I'll show you a business with bad financials 'cause they're gonna come, they're gonna be hand in hand," Conway explains.

His formula is straightforward but demanding: plan marketing spend to match seasonal needs, use ServiceTitan to tag aged equipment throughout the year, maintain a ratio of 350 agreements per technician, and never stop investing in people.

The math is simple, the execution requires discipline.

John Conway recently joined ServiceTitan’s Jackie Aubel on the “Toolbox for the Trades” podcast, which included Conway’s thoughts on:

[6:38] Why adding plumbing and electrical reduces seasonal dependency

[10:00] Using ServiceTitan to tag aged equipment for strategic callbacks

[15:00] The 350 agreements per technician benchmark for stability

[18:00] Breaking down membership value: $2,300 in services for $199

[23:00] Common planning pitfalls that keep businesses seasonal

[26:00] How culture directly impacts financial performance

Additional Resources:

Nexstar Network

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