About Gerard
Gerard O’Shea focuses his practice on employment counseling and litigation for clients ranging from early stage startups to Fortune 100 companies. With a deep understanding of both employment law and corporate matters and transactions, including financings, he helps clients understand employment-related legal issues in the context of running a business, which allows him and his clients to formulate business-practical solutions to reflect, manage, and mitigate legal risk in savvy and business-practical ways.
Gerard helps clients grow their businesses and retain talent by drafting client employment agreements, offer letters, confidentiality agreements, invention assignment agreements, commission plans, handbooks, noncompetition and nonsolicitation agreements, and other employee policies.
He helps clients protect their businesses by assisting clients with hiring, firing, and everything in-between, including sensitive employee matters; managing and structuring reductions-in-force; handling the lifecycle of employee discrimination, harassment, and retaliation claims, including investigations and negotiations; and counseling clients on and litigating employee mobility issues, including enforcement of employee non-competes upon termination and risk management relating to hiring.
Gerard helps clients navigate lawsuits and audits by representing them in federal and state court, and in proceedings before the Equal Employment Opportunity Commission, Department of Labor, Office of Federal Contract Compliance Programs (OFCCP), and various city and state agencies.
He helps his clients get funded and achieve profitable exits by representing their employment-related interests on both the buy and sell sides in M&A transactions and in connection with fund-raising. He has worked on several hundred M&A transactions over the past two decades.
Gerard helps his clients expand to new countries and territories, including assisting UK, European, and other non-US clients to seamlessly expand in the US by leveraging his extensive experiences with non-US clients, EU citizenship, and prior legal education in Europe.
In addition, Gerard is a thought-leader and expert in business modeling gig economy businesses to withstand misclassification audits and lawsuits, comply with the multitude of applicable legal standards, and attract savvy investors. In that capacity, he advises and represents many of the country’s leading on-demand businesses in mission-critical lawsuits and audits, including reviews before the IRS, New York State Department of Labor, and California Employment Development Department.
Education
Cornell Law School
JD, 2004
Boston College
BA, Pre-Medical/Psychology, cum laude, 1999
Court admissions
US Court of Appeals for the First Circuit
US District Court for the Southern District of New York
US District Court for the Eastern District of New York
US District Court for the District of Massachusetts
Rankings and accolades
Best Lawyers: Litigation – Labor and Employment (2025)