Mastering Sales Execution: Cory Bray on Sales Enablement, AI, and Strategy Alignment

Overview

In this revealing episode of "The Gap," sales expert Cory Bray tackles the persistent disconnect between strategy and execution that drains revenue potential from even the best companies. When your sales team struggles to turn boardroom plans into field results, the conversation uncovers what's really happening in that gap and how modern revenue enablement can solve these challenges.

Takeaways

1. Understanding Strategy vs. Tactics:

Cory clarifies the often confused difference between goals, strategies, and tactics. He points out that strategy gets misused frequently, especially by middle managers. According to Bray, true strategy belongs at the executive level and aligns with company-wide goals. The real work happens in the tactical execution, where sales teams need to focus their energy and attention.

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"The goal is being set by the CEO, the board of directors...The strategy is being set by the executive leadership team... and the tactics are being executed by the company at large."

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2. The Tactical Role of Sales Enablement:

Challenging conventional thinking, Cory argues that sales enablement teams shouldn't be developing strategies but executing on them. Their primary job is implementing tactics that support leadership's strategic vision. Sales enablement tools should make this process more effective by helping teams organize and deploy these tactics with precision.

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3. Project Management: The Missing Competency

One of Cory's most pointed observations centers on a fundamental skill gap in enablement teams: project management and analysis. "Where along that journey does somebody develop really strong project management skills? It doesn't happen," he notes. Without these abilities, teams struggle to prioritize work, measure results, and execute consistently. Cory suggests a straightforward "0-1-2" framework (didn't do it, did it, did it well) for assessing execution quality.

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4. Common Sales Execution Challenges

The conversation highlights several roadblocks that prevent effective sales execution:

• Inconsistent project management approaches
• Goals that don't align across departments
• Superficial deal analysis and management
• Weak understanding of target markets
• Poor preparation for handling objections

Whether stemming from product-market misalignment or inconsistent sales fundamentals, these issues significantly impact performance. Addressing them requires a return to mastering the basics.

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5. The Double-Edged Sword of AI in Sales

Cory takes a nuanced view of AI in sales enablement tools. While acknowledging its benefits for insights and automation, he warns about its potential to undermine critical thinking.

"AI makes people smarter and dumber at the same time."

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He emphasizes that AI works best as a complement to human judgment, not a replacement. Sales professionals still need to maintain their critical thinking abilities to navigate complex sales situations effectively.

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6. Leadership and Alignment

Successful sales strategy implementation demands strong leadership that aligns the organization around common objectives. Leaders need to set clear expectations while supporting their enablement teams through the execution process.

"You can't raise 18 children in one year, just like you can't implement massive change overnight."

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Patience combined with alignment drives sustainable success. Cory also cautions against constantly rebuilding programs rather than improving existing ones: "Building stuff's easy... Taking something that kind of works and making it work, that's harder."

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How Revenue Enablement Platforms Solve These Challenges

Today's revenue enablement platforms are revolutionizing sales and directly address the gaps Cory identifies by offering:

• Project management tools that give structure to enablement initiatives
• Analytics that pinpoint execution gaps across sales organizations
• CRM integration for real-time visibility into deal progress
• Coaching frameworks that strengthen essential sales fundamentals
• Execution scorecards based on practical assessment methodologies

These platforms create the missing bridge between high-level strategy and day-to-day execution, ensuring sales teams can access the right content, training, and guidance exactly when needed.

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Frequently Asked Questions

What is the biggest gap between sales strategy and execution?

According to Cory Bray, the biggest gap typically lies in project management skills. Many teams lack the ability to prioritize, implement, and consistently operate enablement programs instead of jumping between initiatives.

How can revenue enablement platforms improve sales execution?

Revenue enablement platforms bring structure, visibility, and accountability across sales organizations. They help teams align on goals, deliver consistent messaging, find the right resources when needed, and measure execution quality through frameworks like the 0-1-2 assessment method.

What role should AI play in sales enablement?

AI works best when supporting rather than replacing human judgment in sales. Its ideal use involves automating administrative work, providing data-driven insights, and surfacing relevant content while leaving strategic decisions to sales professionals.

How can sales leaders better align strategy with execution?

Sales leaders should focus on setting clear goals, consistently communicating priorities, building project management capabilities, and creating accountability through simple assessment frameworks that make execution quality measurable.