How RRCA Roofing Turned Sales Careers into Entrepreneurial Launchpads

by William Jones / ⠀Entrepreneurship / July 30, 2025

One of the essential distinctions between a job and a career is the opportunity for growth and future success within the role. When Stephen Kaywell became a door-to-door sales rookie in 2013, he wasn’t sure what to make of the position. However, after realizing his exceptional talent as a salesperson, he began to aspire to greater goals. Today, he is the National Sales Manager at RRCA Roofing, and his journey exemplifies the company’s high-performance culture, mentorship-driven growth, and innovative response to industry challenges.

Now, he strives to create a work environment full of potential and promise for all, enabling everyone to work in a career where they can succeed. As a result, RRCA has become a top-tier opportunity for ambitious sales professionals.

Entrepreneurial Development Model

RRCA operates in Florida and Connecticut, states where wind and hail storms frequently damage roofs and strain budgets. The company’s hybrid insurance-to-retail model allows homeowners to receive critical repairs quickly, while RRCA ensures cash flow and keeps projects on track. Kaywell believes that this same agility provides recruits with a rare opportunity. RRCA’s culture goes beyond hiring salespeople; it aims to develop entrepreneurs. Through mentorship, leadership development, and financial literacy, recruits learn to think like business owners. They participate in mentorship programs that combine field training, leadership coaching, and personal growth, something Kaywell wished for himself. Kaywell emphasizes that for those committed, “the teacher appears,” highlighting RRCA’s performance-focused environment and the genuine chance to earn six figures. Through it all, Kaywell’s approach emphasizes self-mastery and vision: “Treat every role as if you’re the CEO of your own enterprise.”

Resilience in a Crisis

When insurers started pulling back from Florida, claims payments slowed significantly, risking contractor projects across the state. Kaywell’s team adapted by securing third-party financing, enabling homeowners to move forward with repairs while waiting for reimbursement. The change not only maintained cash flow but also strengthened RRCA’s reputation as a client advocate. This became a proving ground for RRCA’s adaptability. The resilience the company demonstrated helped to build trust and long-term relationships with clients and employees alike; two rare traits in high-velocity sales environments.

High Earnings, Real Impact

The combination of recurring natural disasters and insurance-to-retail agility creates a uniquely lucrative niche for reps who perform. This was what Kaywell realized in 2013 when he first began his career in sales. Raised by a single mother who taught him that hard work and belief can rewrite any script, Kaywell leans on those lessons daily. “Whether you think you can or you can’t, you’re right,” he says, echoing the entrepreneurial mindset that propelled him from novice rep to closing more than $1 million in contracts every year since 2020.

Market Insight & Industry Relevance

In 2024, Florida had the highest average annual home insurance premium at $6,000, more than triple the U.S. average of $1,700 (Source: Insurance Information Institute, 2024). RRCA’s customer education model and sales training help bridge the trust gap between homeowners and contractors, making sales reps not just closers but advocates.

Self-Made Success

Everyone aspires to be successful. If you employ someone and continuously tell them that they are little more than a cog in the machine of the larger company, they’re not going to be inspired to work harder. However, if you give that same employee the opportunity to grow and build a better future for themselves within the company’s structure, they are much more likely to become a dedicated worker, because their job has now transformed into a career for them. With RRCA roofing, Stephen Kaywell is doing precisely that; affording people the opportunity to become their own self-made success story in a bold new market.