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

How to Engage Hard-to-Reach CXOs: The New Growth Playbook

How to Engage Hard-to-Reach CXOs: The New Growth Playbook

Sun, Oct 25, 2026 | Posted by Ron Greenberg

 

Executive Takeaways

  • Hard-to-reach CXOs engage when you provide insights connected to the business outcomes they own.
  • Developing meaningful insights takes extra effort, synthesizing data, research, and discussions—to identify where new value can be created.
  • The insights that matter explain what is changing and why—and where new value or growth can be created.
  • Building these capabilities results in a more repeatable path toward achieving executive engagement, lasting relationships, and growth.

This blog is part of Chief Outsiders’ New Growth Imperative series, designed to help CEOs and leadership teams engage executive decision-makers at targeted strategic accounts by turning deep insights into compelling customer value.

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