Skillsoft appoints Matthew J. Cushing as Chief Legal Officer
Skillsoft appoints Matthew J. Cushing as Chief Legal Officer effective August 3, 2026, succeeding interim leader Scott Semel. Cushing brings extensive experience from Pegasystems, EnerNOC, and Acme Packet, including overseeing Oracle’s $2.1 billion acquisition of Acme Packet. He will report to CEO Ron Hovsepian and lead the global legal organization.

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Skillsoft (NYSE: SKIL) has appointed Matthew J. Cushing as its Chief Legal Officer, effective Monday, August 3, 2026. The appointment marks the completion of a planned transition to permanent leadership for the company’s legal function, replacing Scott Semel, who served as interim Chief Legal Officer. Cushing will lead Skillsoft’s global legal organization and report directly to Chief Executive Officer Ron Hovsepian.
The hiring brings three decades of experience in legal, governance, commercial strategy, and business transformation to the AI-native skills management platform. CEO Ron Hovsepian stated that Cushing’s firsthand experience in helping companies navigate complex business transitions while maintaining strong governance and operational discipline will be an asset as Skillsoft continues executing its strategy and driving growth.
Executive Background
Before joining Skillsoft, Cushing held multiple executive leadership roles at Pegasystems for nearly nine years. He served as General Counsel (Chief Legal Officer) and Chief Commercial Officer, leading the global legal function during Pegasystems’ transition to a cloud-first subscription business and a period of significant Annual Contract Value (ACV) growth.
Earlier in his career, Cushing was Vice President and General Counsel of EnerNOC, where he helped lead the company’s successful U.S. Supreme Court litigation in FERC v. EPSA. He also served as Vice President, General Counsel and Secretary of Acme Packet, leading the legal execution of Oracle Corporation’s $2.1 billion acquisition of the company. Prior to these roles, he spent 17 years at Bingham McCutchen LLP (now Morgan Lewis), including more than a decade as a partner in the firm’s corporate practice.
Leadership Transition
Cushing’s appointment concludes the interim period led by Scott Semel. Hovsepian expressed gratitude for Semel’s leadership and contributions during the transition.
Cushing cited Skillsoft’s clear vision, strong leadership team, and significant opportunities ahead as key factors in his decision to join. He emphasized his intent to contribute to the company’s continued growth and create long-term value for shareholders.
What This Means for Governance
The appointment strengthens Skillsoft’s executive leadership team with a veteran public company executive experienced in both legal compliance and commercial strategy. By integrating legal oversight with commercial acumen—reflected in Cushing’s prior dual role at Pegasystems—Skillsoft aims to align its governance framework more closely with its operational and growth objectives. This structural alignment is particularly relevant as the company advances its AI-native platform strategy and manages workforce capability transformations for its clients.
How might Matthew Cushing's dual background in legal and commercial strategy influence Skillsoft's upcoming contract negotiations and revenue recognition practices?
What specific governance challenges does Skillsoft anticipate facing as it scales its AI-native platform, and how is the new CLO prepared to address them?
Could Cushing's experience leading Pegasystems' transition to a cloud-first subscription model provide a roadmap for Skillsoft's own operational efficiency improvements?






























