Building a stronger home service business

By Jesse Sanchez. 

Contractors can strengthen operations, improve profitability and prepare for a rapidly changing home service market through continuing education and stronger business systems. 

Contractors heading into 2027 are facing rapid changes in marketing, technology, competition and consumer behavior. On this episode of Roofing Road Trips®, Heidi J. Ellsworth spoke with Jim Leslie, CEO of Home Service Freedom, about how continuing education can help contractors adapt and build stronger businesses. 

Before joining Home Service Freedom, Jim helped grow A1 Garage to approximately $350 million and served as chief marketing officer as the company expanded across multiple markets. That experience now shapes his work helping home service contractors improve through training, best practices and peer collaboration. Reflecting on why exposure to other successful businesses matters, Jim explained, “I think the biggest thing is just getting around a group of companies that are scaling rapidly and seeing what's possible opens a whole new dimension.” 

That perspective is especially important as marketing continues to evolve. Search behavior has shifted with artificial intelligence summaries, ChatGPT, Siri, voice search and other options changing how consumers find businesses. Jim described the convergence of those changes with growing consumer skepticism, noting, “I call it the trust recession.” 

For contractors, responding to that environment requires more than generating leads. Understanding profitability, creating repeatable systems and identifying the operational drivers behind performance are also essential. Home Service Freedom addresses areas including marketing, recruiting, sales training, inside sales, operations and organizational development. 

Those topics also shape Freedom 2026, scheduled for October 25-28. The event brings together business leaders, technology executives and experienced home service operators, while providing opportunities for contractors to learn directly from one another. Jim emphasized the value of looking beyond one’s own trade, explaining, “When you expand your horizons and start looking at other industries and seeing what you can take, you just open your mind to all these other possibilities.” 

Beyond the annual event, Home Service Freedom offers workshops, virtual education and year-round training designed to help contractors strengthen their teams and build more scalable operations. 

Listen to the podcast or Watch the conversation to learn more about how continuing education, stronger systems and peer collaboration can help contractors prepare their businesses for growth in 2027!