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

Are You Building a Business That's Ready to Scale - or Just a Business That Has Had Great Growth?

Are You Building a Business That's Ready to Scale - or Just a Business That Has Had Great Growth?

Mon, Jul 27, 2026 | Posted by Carol Eversen

 

Executive Takeaways

  • The commercial function that got you to $10M–$15M was built for that stage. It doesn't automatically scale to the next one.
  • Most founders don't see the gap from the inside. Buyers will see it immediately.
  • Seven diagnostic signals reveal whether your revenue engine is built to scale — or just built for today.
  • The earlier you find the gaps, the less expensive they are to close.

There is a version of business success that feels like momentum but isn't quite there yet.

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