Marketers are an adaptable bunch. When a once-reliable channel starts to dry up, they rarely panic. There’s usually a warmed-up alternative ready to step in. When cost per lead begins creeping up, demand gen teams are quick to experiment—testing new platforms, refreshing creative, or fine-tuning audience segments—until efficiency is restored.

Even as we inch further down the funnel, demand-minded marketing teams tend to shine. They excel at optimizing the conversion rate between leads and opportunities, for example. The mechanics of the pre- and upper-funnel—awareness, engagement, nurture—are well understood, measurable, and adjustable.

But there’s one metric that often proves more stubborn: opportunity-to-win rate.

Maybe it’s because there are so many cooks in the kitchen—demand gen, product marketing, sales, sales development, sales enablement, revenue ops—or perhaps because the “human element” starts to enter the equation. Either way, turning around a declining win rate is one of the toughest challenges go-to-market leaders face.

The cost of generating a qualified opportunity is already high—and with digital saturation, it’s climbing even higher for many B2B companies. That makes win rate arguably the most critical performance metric in any go-to-market system. Improving it even slightly can boost top-line performance and relieve pressure on the top of the funnel. After all, the better the win rate, the fewer leads a marketing team needs to generate.

Yet when opportunity-to-win rates start to decline, the root causes are rarely clear—or confined to a single department. The truth is: restoring win rate is a multi-factorial, cross-functional challenge.

Sometimes the problem is entirely self-inflicted—like sunsetting post-opportunity marketing programs or changing how opportunities are defined in CRM. Other times, it’s largely external: new competitors enter the market, budget freezes hit, or regulatory shifts slow deal velocity.

That’s why we created this visual checklist. It’s intended to be a collection of “prompts”– to ask your colleagues in companies with a conventional tech stack, or your GTM-integrated LLM (for companies that have taken a more aggressive posture around AI tooling). While this resource alone may not single-handedly reverse a declining win rate, hopefully it helps point you toward the change—or combination of changes—that can.

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