Customer Experience, Service & Success

Digital Experience Management Leader Lakeside Names New CEO

The appointment of Lakeside's new CEO coincides with the company's next phase of growth as it opens Boston headquarters
customer service experience

Lakeside Software, the leader in digital experience management (DEM), today announces that Michael Grossi has been named chief executive officer. Grossi brings more than 30 years of expertise across leading software technology segments and verticals, and over the past 5 years, has led transformative growth across private, public, and private-equity B2B software companies. Additionally, Lakeside Software is opening a new Boston office that will serve as the company’s corporate headquarters. Located in Boston’s Downtown Financial District at 2 Oliver Street, this move serves to further accelerate Lakeside’s hiring plans and expedite Lakeside Software’s growth and expansion.

Michael Grossi’s background is a great addition to the team as we continue to scale the business to address the growing DEM market opportunity,” said Mike Triplett, managing director at Insight Partners. “Lakeside has experienced significant growth year over year, and our new office in Boston marks our latest geographical expansion and plays an important part of our strategic growth strategy.”

Grossi succeeds Lakeside founder Mike Schumacher, who is transitioning from his role as CEO to his new role as chief strategy officer. “As Lakeside continues its growth ramp, I’m pleased to have Michael on board, driving that growth to new levels,” said Schumacher. “I’m looking forward to continuing to play a critical role in Lakeside Software’s growth trajectory as I lead strategy and technology solution efforts.”

The rapidly evolving hybrid and remote workforce challenges facing IT departments amid the pandemic has reduced visibility into end user experience and presents a significant market opportunity in the digital experience management space. Lakeside’s DEM platform with its unique Intelligent Edge-based analytics helps customers tackle those challenges by enabling them to proactively measure, analyze, and optimize their employees’ digital experience anywhere they are working.

Lakeside’s Digital Experience Cloud manages and optimizes millions of endpoints for customers in more than 40 countries and six continents around the world today. The company already employs 25 people in the Boston office and is hiring aggressively in Boston, Michigan, and around the globe to meet growing customer demand for the company’s solutions.

“I am thrilled to be joining Lakeside Software, a true leader in the DEM space,” said Michael Grossi. “I look forward to helping accelerate Lakeside’s growth and further strengthen the company’s position and domain expertise across the many areas where customers derive value from Lakeside, including end-user experience management, digital workplace planning, IT asset optimization, remote work management, and proactive service desk operations.”

Most recently, Grossi served as CEO of HealthcareSource, a leading SaaS talent management solution for the healthcare industry and led the sale of the company to symplr®, backed by Clearlake Capital earlier this year. As CEO, he led HealthcareSource through a significant growth phase and transition to a SaaS model. Prior to HealthcareSource, Grossi served as CEO of Ipswitch Software, a provider of IT management solutions for enterprise customers and was acquired by Progress Software in 2019.

Grossi lives in the Boston area with his wife and family and will be based in the new Boston office.

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