John Blessing

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As the Chief Outsiders Chief Sales Program Manager and CSO, John is an accomplished leader who consistently builds success in growth and turnaround situations in a variety of industries, including professional and financial services, retail, and SaaS. He turns around poor performance and accelerates growth by building and executing strategic sales programs. He also drives sales and operations alignment to deliver breakthrough revenue. With experience in several industries, John offers perspectives not hindered by industry-specific paradigms.
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Recent Posts

Growth Without Guesswork: The Questions Great Vistage Chairs Ask

Growth Without Guesswork: The Questions Great Vistage Chairs Ask

Fri, May 15, 2026 | Posted by Karen Hayward

Executive Takeaways

  • Most CEOs are managing growth on assumptions that no longer reflect how buyers actually buy.
  • The best Chair question isn't "how is sales going?" It's "where are the growth leaks?"
  • AI search is already a revenue issue, not a future one.
  • Insight without commitment is just a good conversation.

After leading more than 150 Vistage workshops, working with hundreds of CEOs navigating growth challenges, and spending more than 10 years as a Vistage member myself, I’ve noticed a consistent pattern in conversations with business leaders. No matter the industry, the symptoms sound familiar.

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