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.
Recent Posts

The Revenue-Ready Marketing Playbook, Part 2: In a Noisy Market, Make Clarity Your Competitive Edge
Tue, Apr 22, 2025 | Posted by Jyotsna Makkar
This is Part 2 of the Revenue-Ready Marketing Playbook, a 4-part series for mid-market CEOs who want marketing to move the needle.
A CEO once said to me, “We know our product delivers real value. Our customers are happy. But when we show up in the market, it feels like we’re saying the same thing as everyone else.”
That stuck with me, not just because it was honest, but because it’s common. In crowded markets, sounding the same is the fastest way to become invisible. Buyers tune out. Sales cycles drag. Margins shrink. And despite how strong your actual offering is, you keep getting boxed in as “just another option.”