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

The Augmented Revenue Engine

The Augmented Revenue Engine

Tue, Aug 18, 2026 | Posted by William Bell

Executive Takeaways

  • Sellers who partner with AI are 3.7x more likely to hit quota.
  • AI doesn't replace sellers. It removes the 75% of work that isn't selling.
  • Win rates climb 30%+ when AI improves every funnel stage, not just one.
  • Waiting doesn't preserve the status quo. It widens the gap to AI-enabled competitors.

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