John Blessing

Picture of John Blessing
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

Vistage Chairs: The Most Dangerous Sales Answer a CEO Can Accept: “We Lost on Price”

Vistage Chairs: The Most Dangerous Sales Answer a CEO Can Accept: “We Lost on Price”

Tue, Oct 13, 2026 | Posted by Karen Hayward

Executive Takeaways

  • When a buyer says “too expensive,” research shows price is rarely the real reason, especially as deal size grows.
  • Your CRM loss-reason field reflects your sales team’s view of the decision, not the buyer’s.
  • “Price” is often a stand-in for unclear value, implementation risk, or low confidence in the outcome.
  • A few points of win-rate improvement can unlock real revenue from the pipeline you already have.

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