Lakeside Software Strengthens Market Leadership with  Organizational Alignment of Products and Strategy Led by Robert Hobbs

Hobbs to Lead Results-Driven Team Across Strategy, Product Management, Product Marketing, and Product Value Delivery

BOSTON, February 12, 2025—Lakeside Software, the first AI-driven digital employee experience company, has unified its strategy and product-focused teams, creating a cohesive group designed to seamlessly align strategy with product, adapt swiftly to market shifts, and deliver an unparalleled product roadmap. Industry veteran Robert Hobbs will lead this team as senior vice president of strategy and products, driving operational agility, enhancing collaboration, and accelerating innovation to meet the evolving needs of modern enterprises. 

With more than 20 years of experience leading product and strategy teams, Hobbs most recently served as Lakeside’s vice president of business development, where he was instrumental in scaling the company’s growth and shaping strategic initiatives that have positioned Lakeside as an industry leader. Prior to joining Lakeside, Hobbs held leadership roles at LHS Communications, Digiquant, and IBBS. 

“Enterprise IT is on the brink of a massive transformation, so they need technology partners who can keep up. Unifying Lakeside’s strategy and products teams allows us to deliver innovative solutions with laser-focused agility and speed,” said David Keil, CEO of Lakeside Software. “Bob’s deep expertise and proven leadership track record make him the ideal person to drive this transformation and elevate our product strategy to meet the demands of our global customer base.” 

Under Hobbs’ leadership, Lakeside will strengthen the connection between products teams and customer-facing teams, ensuring real-time feedback loops that drive faster innovation. By aligning product performance with customer insights, Lakeside is uniquely positioned to accelerate its mission of delivering AI-driven intelligence that transforms digital environments and empowers organizations to optimize their operations. 

“I am deeply honored to lead this high-performing team and to play a pivotal role in shaping the future of Lakeside,” says Hobbs, SVP, Strategy & Products. “In today’s fast-evolving business landscape, enterprises are placing an unprecedented focus on the digital employee experience—and Lakeside is uniquely positioned to lead this transformation. Our vision is to unleash human productivity by delivering flawless digital experiences. Let’s usher in a new era of IT where enterprises can optimize IT operations, drive down costs, and boost productivity—while crafting a seamless, high-performance digital experience for every user.” 

Lakeside began 2025 with significant market acceleration following the launch of its SysTrack Intelligence Package in July 2024. This innovative solution has revolutionized IT operations by leveraging Lakeside’s differentiated collection of high-quality, well-structured IT data and proactive IT capabilities to create AI models purpose-built for IT. With several large Q4 Intelligence Package bookings and expanding market interest, Lakeside is positioned to further expand its AI and DEX leadership in 2025.