Bridging Generations in Sales and Outreach

E11 with Walter Crosby - Cigars, Sales Teams, and Straight Talk for CEOs


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In this episode, Butch Nicholson sits down with veteran sales strategist Walter Crosby, host of the Sales and Cigars podcast, to explore why so many sales teams struggle to reflect the vision of the CEO and how to fix it.

Walter shares insights from four decades in the field, helping business owners identify broken systems, misaligned incentives, and outdated hiring practices that quietly hold their sales teams back.

You’ll hear why relying on “industry experience” is often a trap, how modern buyers are changing the rules, and what CEOs must do to align compensation, culture, and clarity inside their sales org.

He breaks down why defining your ICP is non-negotiable, what it takes to motivate different generations on your team, and why LinkedIn is a credibility tool not a cold call shortcut.

If you're a Gen X or Boomer business leader trying to modernize your sales approach without losing your edge, this conversation is a masterclass in building a professional sales team that actually performs.

Bridging Generations in Sales and Outreach is hosted by Robert (BUTCH) NICHOLSON and produced by Fist Bump

Helping Gen X and Baby Boomer leaders turn their reputation into revenue—without losing the human touch.

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Bridging Generations in Sales and OutreachBy Butch Nicholson