Former Snyk CRO Gary Olson and Former Zscaler VP Crendal Kear join Sysdig to propel the company toward $250 million ARR, following outsized growth in user adoption

Amid Global Expansion and >330% Growth of Sysdig Sage™ AI, Sysdig Appoints Gary Olson CRO and Crendal Kear CBO

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Damon Weinhold
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Sysdig, the leader in real-time cloud security, today announced the appointment of Gary Olson as Chief Revenue Officer (CRO) and Crendal Kear as Chief Business Officer (CBO) following a remarkable 337% growth in Sysdig Sage™ user adoption over the last eight months. Sysdig Sage, the industry’s first agentic artificial intelligence (AI) cloud security analyst, uses multi-step reasoning and contextual awareness to help security teams find, understand, and fix issues faster. By accelerating human response, Sysdig Sage equips organizations to outpace attackers and decrease cost per incident by >50%.

Demand for Sysdig Sage has surged over the last eight months, with more than 45% of customers already adopting the technology – a spike attributed to the company’s pioneering approach to AI-embedded cloud security workflows. By leveraging contextually aware AI agents with domain-specific expertise, Sysdig Sage bolsters enterprise cloud security and redefines operational efficiency.

Sysdig closed its fiscal year with more than 400% expansion across Europe, the Middle East, and Africa over the last 24 months. The company also secured top customer ratings for both cloud-native application protection platforms and cloud security posture management in Gartner Peer Insights™, and remains the only company to receive a perfect 5 out of 5 score for Support Experience in the two Gartner “Voice of the Customer” reports.

“I spent my first 100 days at Sysdig traveling the world to meet with customers, and one thing was clear: they love our products. The rapid adoption of Sysdig Sage, the fastest in our history, is a strong signal of the massive opportunity ahead,” said William Welch, Sysdig CEO. “I’m focused on building a world-class executive team with public company experience and a commitment to operational excellence. Reuniting with Gary and Crendal from our time at Zscaler, as well as appointing a new CMO and CISO last year, positions Sysdig to drive innovation in cloud security as we push toward $250 million ARR and beyond.”

Olson Joins as CRO to Drive Sysdig’s Next Phase of Growth

With proven experience scaling high-performance teams and delivering rapid, repeatable revenue growth, Gary Olson brings over 30 years of experience in cybersecurity and software-as-a-service (SaaS) to Sysdig. Most recently, as CRO at Snyk, he led a global team of more than 300 to achieve a $300 million annual recurring revenue (ARR) milestone in just one year. Before that, he played a key role in Zscaler’s go-to-market (GTM) expansion, launching and growing a new product and sales team globally, and contributing to the company’s successful initial public offering (IPO). Olson has also held senior leadership positions at AT&T Cybersecurity (now LevelBlue), BMC Corp., Blue Coat Systems, Sun Microsystems, and PTC.

“Sysdig stands out in cloud security with the industry’s fastest cloud detection and response, seamlessly correlating data across dynamic cloud environments in real time,” Olson said. “At the core of this capability is Falco – the trusted, open source cloud detection standard used by over 60% of the Fortune 500. If you’re looking for the best cloud detection and response, you go to the company that set the standard.”

Kear Appointed CBO to Scale Sysdig for Long-Term Success

Over a career that spans high-impact roles at cybersecurity and enterprise technology leaders, Crendal Kear has built a reputation for fostering collaboration and empowering teams to shatter goals. At Talkdesk, she led global customer success, enhancing client retention and satisfaction. At Zscaler and Exabeam, she streamlined GTM motions and drove scalable revenue growth. During her extensive tenures at HP, NetApp, and Aricent, Kear transformed business operations, aligning strategy with execution for long-term success.

“The cloud security market is at a pivotal moment and, as the real-time cloud security leader, Sysdig is in an ideal position,” Kear said. “Given the substantial European expansion, the global adoption of Falco, and the rapid evolution of Sysdig Sage, we have a tremendous opportunity to redefine how businesses approach security in the cloud. My focus is to build the operational rigor necessary to scale our GTM motion, optimize execution, and ensure that customers receive a best-in-class experience.”

Resources

• Meet Gary Olson and Crendal Kear on LinkedIn.
• Learn more about the Chief Information Security Officer and Chief Marketing Officer who joined Sysdig in December 2024.
• Learn more about Sysdig.

About Sysdig

In the cloud, every second counts. Attacks unfold in minutes and security teams must protect the business without slowing it down. Sysdig, named Customers’ Choice in the Gartner® “Voice of the Customer” report for cloud-native application protection platforms (CNAPPs), stops cloud attacks in seconds and instantly detects changes in risk with real-time insights and open source Falco. Sysdig Sage™, the industry’s first AI cloud security analyst, uplevels human response and enables security, developers, and DevOps to work together, faster. By correlating signals across cloud workloads, identities, and services, Sysdig uncovers hidden attack paths and prioritizes real risk. From prevention to defense, Sysdig helps enterprises focus on what matters: innovation.

Sysdig. Secure Every Second.

View source version on businesswire.com: https://www.businesswire.com/news/home/20250313971850/en/

Amid global expansion and >330% growth of Sysdig Sage™ AI, @Sysdig appoints Gary Olson CRO and Crendal Kear CBO. Learn more: https://sysdig.com/press-releases/gary-olson-appointed-cro-crendal-kear-appointed-cbo/