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.
Find me on:

Recent Posts

The CEO Dashboard Should Show Direction, Not Just Activity

The CEO Dashboard Should Show Direction, Not Just Activity

Thu, Oct 15, 2026 | Posted by Paul Sparrow

If your dashboard only tells you what happened, it’s reporting history. A CEO needs direction.

Steps Taken Aren’t the Same as Direction

I've spent a fair amount of time backpacking, and one thing becomes obvious when you've been walking for several hours: knowing how far you've walked isn't the same thing as knowing whether you're headed in the right direction.

Your watch can tell you that you've taken 22,000 steps.

Read More