Lakeside Software Expands Leadership Team with Appointment of Tyler Winkler as Chief Commercial Officer

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New role will drive revenue and market share growth through customer and partner expansion

BOSTON, September, 8, 2022 — Lakeside Software, the leader in digital experience management, announced today that Tyler Winkler has joined the company as chief commercial officer. In this new role, Winkler will oversee a global team of executive leaders and drive the company’s direct and channel sales strategies and operations.

Winkler brings to Lakeside three decades of executive leadership experience within the enterprise software space. As VP of Global Sales & Marketing at SecureWorks, he was instrumental in the company’s growth and success, which led to a $650 million acquisition by Dell in 2011 and a subsequent IPO in 2016. He joins Lakeside from UserIQ, a predictive customer success platform, where he served as CEO and a member of the company’s board of directors prior to its acquisition in August 2022. His deep-rooted software experience and success in growing high-performing sales teams add expertise and experience to Lakeside’s executive team.

“Tyler’s appointment is a momentous step forward for Lakeside as we continue to strengthen our leadership team and scale our global sales coverage,” said David Keil, CEO of Lakeside Software. “Tyler has an incredible reputation in the software industry which will help us to hire the best in the industry and accelerate our growth. His leadership and experience will greatly enhance our ability to exceed our customers’ expectations and emerge as the leader in the DEX market.”

“I am pleased and proud to join Lakeside’s executive leadership team,” said Winkler of his appointment. “Lakeside is rapidly expanding to meet the demands of enterprise organizations worldwide, and I’m excited to help lead and develop our sales and go-to-market strategy. Our best-in-class product and deep data collection provide companies with the right tools and insights to drive their business forward. I look forward to increasing its product accessibility through direct and channel partners.”

This is the latest in a series of significant developments for Lakeside in 2022. In June, Lakeside expanded the executive leadership team by appointing Elise Carmichael as chief technology officer; Guy Lever as senior vice president of customer success; and Ayelet Elstein as vice president of EMEA.

In August, Lakeside was named a Leader in The Forrester Wave™: End-User Experience Management, Q3 2022 report. Among the evaluated EUEM vendors, Lakeside was cited for enabling deep historical analysis of telemetry data for root cause analysis. Lakeside’s telemetry monitoring was also scored highest — a benefit of the Intelligent Edge architecture found in its Digital Experience Cloud platform, which collects more than 10,000 metrics out of the box.

About Lakeside Software

Lakeside Software is a leader in cloud-based digital experience management. Lakeside’s Digital Experience Cloud, powered by SysTrack, gathers and analyzes data on everything that may impact end-user experience and business productivity and provides the unmatched visibility IT teams need to design and support rapidly changing digital workplaces. Customers use Lakeside’s technology to perform end-user experience management, digital workplace planning, IT asset optimization, remote work management, and proactive service desk operations. For more information, visit

Lakeside Software and SysTrack are registered trademarks and/or trademarks of Lakeside Software, LLC in the United States and other jurisdictions. All other trademarks and registered trademarks are property of their respective owners.

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