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

Outsider Insights | From Hustle to System: Why More CEOs Are Rebuilding Their Sales Function

Outsider Insights | From Hustle to System: Why More CEOs Are Rebuilding Their Sales Function

Mon, Nov 3, 2025 | Posted by Dawn Werry

Outsider Insights

Across Chief Outsiders, we talk to hundreds of CEOs every month. In this new series, we explore the trends and challenges we’re hearing from these discussions – and what you can do if you’re facing the same issues in your business.

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