Raymond Little on Sales Leadership: Leading From The Front

About this episode

Raymond Little discusses effective sales leadership and strategies in the roofing industry.

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…

People in this episode

Host: Tim Brown

Guest: Raymond Little

Topics covered

• sales leadership
• roofing industry
• personal development
• team building
• sales tactics

Keywords

• roofing sales
• storm claims
• retail market
• hiring philosophy
• personal development

Mentioned in this episode

Organizations: SVG Roofing Coaching, Contra Shoes

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• Building Owl Roofing: The Story Behind the Growth · May 5, 2026 · 38 min
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