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

When the Founder Is the Rainmaker: How to Scale Without Losing the Spark

When the Founder Is the Rainmaker: How to Scale Without Losing the Spark

Mon, Jul 7, 2025 | Posted by Paul Sparrow

In many founder-led businesses, the founder isn’t just the leader—they’re also the best (and often only) rainmaker. They land the big deals. They have the trusted relationships. They know the pitch inside and out because they are the pitch.

It works—until it doesn’t.

As the business grows, this model creates a bottleneck. Every new opportunity depends on one and only person. And it’s the same person every time. But there’s a downside. When that person is also responsible for running the business, mentoring the team, and shaping the vision, something eventually gives.

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