Startup News

AI Startup Skillsoft Appoints Matthew J. Cushing as Chief Legal Officer

Aug 4, 2026 | By Devin Jacobs

Skillsoft has appointed Matthew J. Cushing as it's Chief Legal Officer, effective August 3. He will lead the company's global legal team and report directly to CEO Ron Hovsepian.

SUMMARY

  • Skillsoft appointed Matthew J. Cushing as Chief Legal Officer.
  • Skillsoft provides an AI-powered workforce skills platform.
  • Cushing will lead the legal team and support the company's growth strategy.

Cushing brings extensive experience in legal leadership, corporate governance, commercial strategy and business transformation. His appointment will support Skillsoft as it continues to execute its growth strategy.

Before joining Skillsoft, Matthew J. Cushing held several executive leadership roles at Pegasystems, including Chief Legal Officer and Chief Commercial Officer.

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During his nearly nine years with the company, he led the global legal team and helped support Pegasystems' transition to a cloud-first subscription business while driving strong annual contract value (ACV) growth.

"The work we've done to reposition Skillsoft has created new opportunities for growth, innovation, and value creation," said Ron Hovsepian, Chief Executive Officer of Skillsoft. "Matt has firsthand experience helping companies navigate complex business transitions while maintaining strong governance and operational discipline.

"I'm excited to join Skillsoft at such an important point in its evolution," said Mr. Cushing. "What attracted me most was the opportunity to join a company with a clear vision, a strong leadership team and significant opportunities ahead.

About Skillsoft

Founded in 1998, Skillsoft provides an AI-powered skills management platform that helps organizations understand their workforce skills, close skill gaps, and measure the impact of employee development. The platform helps businesses build AI ready teams, reduce the cost and time of training, and prepare employees for changing workplace needs.

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