Raymond Little on Sales Leadership: Leading From The Front

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