April 28, 2026 • 45 Minutes

Raymond Little on Sales Leadership: Leading From The Front

Guest: Raymond Little — Founder, SVG Roofing Coaching | Contra Shoes

Guest Links: Facebook: Raymond Wendell Little | Instagram: https://www.instagram.com/rwl612/

Raymond Little built a roofing company from zero to nearly $100 million, exited to private equity for $40 million, and now runs SVG helping owner-operators between $1M and $10M break through their plateaus. In this episode, Raymond gets raw about what actually works in roofing sales in 2026, starting with storm vs retail in today's market, why wind claims are getting harder everywhere, and why the four-to-eight knocking window beats the nine-to-five mindset most new companies are still stuck in. He breaks down why you should never poach million-dollar producers from other companies but instead build them yourself, why a hefty override or ownership needs to be in the field driving the team daily, and his rule that you can't develop anyone greater than yourself. The conversation digs into Raymond's hiring philosophy built around second-chance people, team players, and good energy over credentials or personality tests, his 90-day ride-along system where new reps work the first 4-5 deals in the truck with him from knock to build, and the sales tactic of using the adjuster and homeowner as "teachers" to elevate new reps while making the process fully transparent. Raymond also shares why personal development around physical health, clean living, and healthy relationships is the foundation his entire company was built on, the real numbers on what 1099 reps should earn per lead, why one roof a week pays the bills and three a week means you stop checking price tags, and his mentor story of following Kurt the Nintendo and hitting half of what that man accomplished as his own definition of success. He also gets into Contra Shoes, the lightweight flexible roofing shoe a quarter the weight of Cougar Paws, designed for reps who knock and climb all day.

Roofing Podcast - Hook Better Leads

Welcome to one of the top Roofing Podcasts for marketing, sales, leadership and technology!

If you're seeking valuable insights and actionable strategies to excel in the roofing industry, you've come to the right place. Our dedicated roofing marketing podcast is your go-to resource for everything related to marketing in the roofing sector. Tune in every Friday and enjoy bonus episodes on select Tuesdays to stay informed and inspired.

Join us as we bring together industry-leading experts who specialize in roofing sales. Our roofing sales podcast is designed to equip you with the knowledge and skills necessary to boost your sales performance and achieve outstanding results. From prospecting and lead generation to negotiation techniques and closing deals, our sales coaches share their expertise and practical tips to help you succeed in the competitive roofing market.

We also dive deep into the realm of roofing leadership. Our podcast features accomplished leaders who have made significant impacts in the roofing industry. Learn from their experiences, strategies, and leadership principles to inspire and elevate your own leadership abilities. From building high-performing teams to fostering a culture of excellence, our roofing leadership podcast provides the guidance you need to become a respected leader in the roofing community.

In addition, we explore the latest trends and innovations in roofing marketing. Stay up to date with the rapidly evolving landscape of digital marketing, social media strategies, and branding techniques tailored specifically for the roofing industry. Our roofing marketing podcast delivers insights that will help you develop effective marketing campaigns, reach your target audience, and grow your roofing business.

Don't miss out on the opportunity to enhance your knowledge and skills in roofing sales, marketing, and leadership. Tune in to our roofing podcast every Friday, and mark your calendars for our special Tuesday episodes that delve deeper into the topics that matter most to you. Stay ahead of the competition and unlock your full potential in the exciting world of roofing through our informative and inspiring podcast.

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