Sales can be high-pressure, but a little humor goes a long way! This blog explores six hilarious sales video moments—from “Sell Me This Pen” to Michael Scott’s role-play disaster—offering both laughs and valuable sales lessons. Whether it’s storytelling like Don Draper or upselling like Eugene Levy, these clips highlight what to do (and what to avoid) in sales. At SmartWinnr, we believe in blending humor with effective training through gamification and sales contests. Want to engage and upskill your team? Discover how SmartWinnr can make sales training fun and results-driven!

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