WHAT WORKS FOR THIS GREAT SALESPERSON TO WIN HUGE DEALS

24 Dec 2024 · 42 min
The Brutal Truth about Sales and Selling - We interview the world's best B2B Enterprise salespeople.

24 Dec 2024 · 42 min

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In this episode Brian Burns interviews veteran Smartsheet salesperson Josh Safford about the mindsets, habits, and strategies that separate great salespeople from average ones. The conversation opens with a contrast between a "tips‑and‑tricks" mindset (minimal effort to hit the next milestone) and a "student of the game" mindset (continuous learning, deep curiosity). Josh recounts his painful transition from a pre‑sales engineer to a quota‑carrying rep, describing the first year as a "callus‑building" period of public mistakes. He explains how he eventually found his groove after six years, emphasizing discovery, personalized engagement, and a visual, analogy‑driven approach (camping, commercial aviation). Josh shares how he manages up by justifying deviations from playbooks, and how his two super‑powers—creativity and an intolerance for loss—help him navigate blockers, test champions, and keep deals alive. He describes his role as a cross‑functional facilitator in a matrix organization, mapping relationships, translating the fluid art of selling into actionable, forecastable data. Throughout, he critiques the modern obsession with formulaic email subject lines and rigid playbooks, arguing that sales is an art that requires adaptability, authenticity, and deep strategic thinking. The episode also promotes tools like brevitypitch.com for safe role‑play practice and highlights the importance of visualizing strategy, focusing on a handful of high‑impact enablement materials, and building genuine champion relationships.

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