What the Middle Market Gets Wrong About Pricing

April 23, 2026

Pricing is the highest-leverage decision a middle market CEO makes. Most of them set it wrong, rarely revisit it, and leave 10-20% of EBITDA on the table every year.

The usual mistakes

Cost-plus pricing. Discounting to win deals you shouldn’t take. Never raising prices because the sales team is afraid customers will leave. Same prices for high-value and low-value customers. These aren’t strategy. They’re habits.

The truth about price increases

I’ve been through dozens of price increases. The sales team predicts 30% of customers will leave. The actual number is usually 3-5%. The CEOs who can stomach the noise are the ones whose margins expand. The ones who can’t stay stuck.

The real unlock

Segment your customers by value delivered, not by size. The ones who get the most value should pay the most. The ones who get less should pay less — or leave. Flat pricing across segments is a gift to your low-value customers at the expense of your high-value ones.

Where to start

Pick your top 20% of customers by profit contribution. What would it take to increase their average price 7% next year? For most companies, the answer is: almost nothing. That single move is often worth a full year of sales effort.

Ready for a direct conversation about your business?

Bill Canady takes a limited number of strategy coaching calls each month with middle market CEOs, founders, and owners who want a direct read on where their company stands and what to do next. No pitch. No fluff. One honest conversation about growth, profitability, and exit readiness. Book your strategy coaching call at billcanady.com.

About the Author

Bill Canady

Bill Canady is a national best-selling author, Founder & CEO of The 80/20 Institute, and a global business leader known for transforming companies into high-performing, profitable enterprises. Over the course of his career, Bill has led multibillion-dollar organizations through their most critical challenges—navigating complex regulatory, investor, and media environments—while consistently delivering profitable growth.

Drawing on decades of executive experience, Bill created the Profitable Growth Operating System (PGOS), a proven framework designed to help leaders cut complexity, focus on the critical few, and accelerate growth. Through The 80/20 Institute, he and his team partner with CEOs, executives, and entrepreneurs worldwide to apply the 80/20 methodology in real-world settings, unlocking revenue growth, margin expansion, and shareholder value.

As both an operator and advisor, Bill’s mission is clear: to give leaders the tools, systems, and confidence they need to achieve sustainable, profitable growth — without sacrificing focus, culture, or execution.

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