The New Rules of Sales Excellence in Cybersecurity

How value selling, MEDDICC, and adaptive discovery are reshaping sales execution across cybersecurity

"Technology is important—but the business outcome is even more critical." That insight captures the essence of our latest episode of In the Spotlight, where we explore what it takes to drive sales excellence in today’s cybersecurity landscape.

In this deep-dive conversation, veteran sales leader Gary Olson (CRO at Sysdig, with prior leadership roles at Snyk, Zscaler, AT&T, and Symantec) joins Spotlight CEO Roi Carmel to unpack the evolving dynamics of go-to-market strategy in a crowded, high-stakes environment.

From Pitch to Partnership: The Shift to Value Conversations

In cybersecurity, product capabilities alone no longer win deals. As buying teams grow more complex and scrutiny increases, sellers must connect deeply with the outcomes that matter most to their prospects.

"What we do as an enabling technology is critical, but what the customer is trying to achieve is even more critical."

Connecting value to business outcomes—early and often—is now the baseline for effective sales conversations.

Sales Excellence = Predictable, Repeatable, Scalable

What separates world-class sales teams from the rest? The formula starts with people, but it’s driven by process:

• Predictable: You know what success looks like

• Repeatable: Everyone can run the same playbook

• Scalable: You can grow without losing quality

More than process or metrics, it’s about building a culture of clarity and purpose—where the story a seller tells is tightly aligned to what the buyer cares about.

MEDDIC: More Than a Checklist

The MEDDIC framework has stood the test of time—but only when applied as a lens, not a formality.

"If you treat MEDDIC like a checklist, it becomes a chore. But if you treat it like a lens on reality—you unlock a whole new way of qualifying."

The key is depth, not just compliance. Great sales teams use MEDDIC to uncover gaps, test assumptions, and shape conversations that lead to decisions.

Adaptive Discovery and the Rise of Human-AI GTM

Modern cybersecurity buyers expect sellers to listen, not pitch. That’s why adaptive discovery—adjusting in real-time based on what you hear—has become essential.

"It’s about shrinking the noise, focusing on the vital few, and adapting conversations around what truly matters."

AI is accelerating this shift. By analyzing interactions, surfacing patterns, and pointing to blind spots, modern sales platforms now enable teams to operate with more precision, more speed, and more insight.

Looking to 2030: A Roadmap for Sales Innovation

What will sales excellence look like five years from now? Think less process and more autonomy.

"I got into a self-driving car and thought: why didn’t we do this 10 years ago? That’s what adaptive GTM will feel like—faster, cheaper, and more focused."

Expect AI to power more of the tactical lift—qualifying, forecasting, researching—so that human teams can focus on strategy, empathy, and customer value.

Final Word

This conversation isn’t just for CROs. It’s for anyone building or scaling a sales motion in cybersecurity—or any other market where complexity, competition, and buyer expectations are rising fast.

"Today is the beginning of the journey to 2030. The way we qualify, communicate, and deliver value will define modern sales."

About the Guest

Gary Olson is the Chief Revenue Officer at Sysdig and a seasoned sales executive with over three decades of leadership experience in cybersecurity and enterprise SaaS. He has held senior roles at companies including Snyk, Zscaler, AT&T Cybersecurity, Symantec, BMC Software, and Juniper Networks. Known for his deep expertise in value selling, MEDDIC frameworks, and building scalable global sales teams, Gary brings a unique perspective at the intersection of sales execution, strategic GTM, and leadership development. He began his career in the U.S. Air Force and continues to serve as an advisor to several startups and venture firms.