Guest: Brett Tesson, Tesson Roofing
Host: Jim Ahlin, Roofing Success Podcast
Listen to the Episode: https://roofingsuccesspodcast.com/wrong-roof-marketing-success-brett-tesson-268
Links:
https://tessonroofing.com
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How One Roofing Mistake Built Unshakable Trust
What happens when your roofing company makes a major mistake—like installing the wrong roof on a customer’s home? If you’re Brett Tesson, founder of Tesson Roofing in St. Louis, Missouri, you turn that misstep into a masterclass in extreme ownership and brand loyalty. In this episode of the Roofing Success Podcast, Brett shares the journey from lawn care entrepreneur to running one of the most respected roofing operations in the Midwest. His story is rich with lessons on leadership, service, and scaling a business by putting people first.
From Lawncare to Leadership: The Birth of Tesson Roofing
Brett’s entrepreneurial journey began with a lawn care business he started in junior college. Hustling by day in landscaping and learning roofing by night, he eventually made the leap into roofing full-time in the thick of the 2008–2009 recession. The industry was struggling, but Brett spotted a key advantage: he had low overhead and a high tolerance for hard work. That mindset, along with a positive outlook and a drive to serve people better than his previous employer, laid the foundation for what would become Tesson Roofing.
“I believed I could serve the clients better. I believed I could bring more fairness to the crews. And if I just focused on working hard for people and not getting too fancy—I could make it work.”
Owning Mistakes and Earning Trust
Perhaps the most compelling moment in this episode is Brett’s story about installing the wrong color roof. The customer had originally chosen tan shingles but later texted to request Moire Black—a message that was missed. When the mistake came to light, the customer gave Brett two options: refund the full project or replace the roof. Brett chose to replace the roof.
“It sucked—but that’s who we are. We want to be known as a company that does what they say they’re going to do.”
The incident wasn’t just handled—it was transformed into a trust-building story. Neighbors saw a crew replacing a brand-new roof and asked what was going on. When they heard Tesson was making it right at no extra charge, that story became powerful word-of-mouth marketing. Brett emphasized that generosity and doing the right thing—even when it costs money—strengthen both brand and team loyalty.
Service as a Strategy: Partners, Not Vendors
Brett doesn’t just talk about service—he builds it into every layer of his company culture. That starts with treating everyone like a partner: clients, crews, and suppliers.
- Customers are treated with respect and proactive communication. Tesson Roofing implemented a CRM system early to ensure every client touchpoint was organized and responsive.
- Crews are supported with Gatorade, lunches, frozen Snickers, and jobsite check-ins. As Brett puts it, “Treat people like humans, not commodities.”
- Suppliers meet with Brett at the beginning of each year to align on expectations and growth goals. His team books jobs 3–5 weeks out and communicates clearly, which earns them favorable pricing and priority treatment.
“If I see a delivery driver at a gas station, I’ll stop and buy them lunch. It’s just appreciation—and it doesn’t cost much.”
Building a Loyal, High-Performance Team
One of Brett’s most impactful leadership decisions was transitioning from 1099 contractors to a fully W2 sales team—before it became industry trend. That meant more overhead, more risk, and some growing pains. But it also allowed Brett to invest deeply in people and build a true team culture rooted in loyalty, humility, and shared purpose.
Every Tesson Roofing team member is salaried, receives a company vehicle and gas card, and is supported with training and resources. Even more important than the perks? The expectation that everyone in the company leads with honesty and service.
“My number one job is to be the lead servant—so they can go out and serve the end customer.”
Many of Brett’s teammates have been in his life since second grade. Loyalty, he says, is earned in how you show up during tough times. His team knows that if something goes wrong, Brett will stand behind them, not throw them under the bus.
Scaling Without Losing Your Soul
With over 40 people on staff (not including subcontractors) and a reputation for quality, Brett has proven that you can scale a business without losing your values. His leadership is about more than delegation—it’s about painting a vision that gives people purpose and helping them see their role in something bigger than a paycheck.
“People want purpose. If they know what they’re doing matters, they’ll go to bat for you.”
His advice to other contractors? Keep your blinders on. Focus on your unique path. Build a business model around your values and plan it out with intention. And most importantly, don’t make everything about money.
Final Thoughts: It’s All About Integrity
At the end of the day, Brett believes that doing the right thing—even when it’s expensive—is the only way to build a company worth working for and worth hiring.
“Money is just the thank-you note. It’s a byproduct of how well you serve people.”
If you’re looking to build a roofing company that customers trust, crews respect, and communities refer without hesitation—Brett Tesson’s playbook is a masterclass in service-first leadership.
FAQs: Roofing Business Takeaways from This Episode
Topic: Customer-Service
Q: How should a roofing company handle installing the wrong roof?
A: Own it, fix it, and treat it as an opportunity to prove your integrity. Brett Tesson chose to replace an entire roof at his company’s expense rather than argue with a customer. This built trust and turned a costly mistake into a powerful word-of-mouth win.
Topic: Operations-Management
Q: How do you scale customer service as your roofing business grows?
A: Use systems like a CRM to maintain communication and service quality. Tesson Roofing implemented theirs early and made it a central part of delivering timely, consistent, and reliable customer experiences.
Topic: Sales
Q: What’s better: a 1099 sales team or a W2 model?
A: Brett moved from 1099 to W2 after realizing he wanted to invest in people long-term. While more expensive, it allowed him to build a more cohesive team culture focused on service, not just commissions.
Topic: Operations-Management
Q: How can you foster loyalty in subcontractor crews?
A: Treat them as partners. Tesson Roofing supports crews with lunches, cold drinks, and genuine respect. That builds loyalty and keeps job quality high.
Topic: Customer-Service
Q: What’s the best way to build trust with clients?
A: Answer your phone, show up on time, and do what you say you’ll do. Simple consistency and follow-through can place you in the top tier of roofing companies.
Topic: Finance-Accounting
Q: Is it worth investing in better compensation and vehicles for staff?
A: Yes—when paired with expectations and culture. Brett provides company vehicles, salaries, and support to his team because he knows that investing in people yields better long-term returns.
Topic: Education-Training
Q: How do you help young team members develop in the roofing industry?
A: Provide mentorship, resources, and purpose. Brett emphasizes servant leadership and purpose-driven work to help young professionals grow with direction and impact.
Topic: Growth-Expansion
Q: When should you invest in switching from 1099 to W2?
A: Once you have a clear business plan and budget, switching can create more structure and accountability. Brett did it after several years in business and has since seen major cultural benefits.
Topic: Marketing
Q: How can customer service mistakes become marketing wins?
A: When you handle mistakes with honesty and generosity, people talk. Replacing the wrong roof voluntarily led to praise from the entire neighborhood—and became a marketing goldmine for Tesson Roofing.
Topic: Legal-Compliance
Q: Why does switching to a W2 model help with compliance?
A: It aligns with labor laws and reduces gray areas in employment practices. Brett also wanted to do things “the right way” legally while building a team-focused culture.
Topic: People
Q: What keeps employees loyal to a roofing company?
A: Loyalty is earned through integrity, investment, and leadership in tough times. Brett’s team knows he has their back, which builds mutual respect and long-term retention.
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