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

From Loyalty Programs to Leadership: What 20 Years in CRM Taught Me About Organizational Growth

From Loyalty Programs to Leadership: What 20 Years in CRM Taught Me About Organizational Growth

Mon, May 11, 2026 | Posted by Anka Twum-Baah

 

Executive Takeaways

  • The principles that build customer loyalty work just as well on your best employees and partners.
  • Salary and bonus are table stakes. What keeps top performers are the moments that make them feel like insiders.
  • Internal friction is as damaging as friction in a customer journey — and just as fixable.
  • Generic recognition retains no one. Tailored moves do.

Loyalty programs taught many of us how to turn casual buyers into raving fans. My 20 years in CRM and loyalty for brands like Marriott, Amazon, and American Express—and leading a $3B customer platform—taught me something bigger: The same system that keeps customers coming back also keeps your best people from leaving.​​ When growth stalls, most CEOs reach for the usual levers: more demand gen, more recruiting, more channels.

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