Kevin D. O'Leary

Kevin O’Leary has practiced law for over twenty-five years, focusing on employment and education.  From 1989 until 2002, he was an associate and then a partner in the Labor, Employment and Benefits group at Cummings and Lockwood, a full-service law firm based in Connecticut.  Kevin spent the next 15 years as Associate General Counsel at Dartmouth College, where he was the attorney principally responsible for responding to employment related issues involving the faculty and the staff, as well as focusing on student affairs matters. In addition, he served as an important part of the team that responded to reports of sexual misconduct, including assault, involving students as the reporting and responding parties.  Kevin has experience advising senior leadership on the development of an effective response to critical issues, taking into account the interests of all parties to the dispute and protecting everyone involved. 

Kevin’s practice has always included investigative work of some form. While in private practice this included helping his clients determine the facts necessary to respond to an internal or an external complaint. At Dartmouth College, he assisted in preparing responses to concerns raised by or about employees, faculty members, coaches and students, relying on his own review of facts in dispute.

Kevin is an experienced investigator and now focuses his work on conducting workplace investigations and providing training that allows organizations to effectively respond to allegations of misconduct and proactively train its staff to avoid these behaviors.  Kevin is trained in conducting forensic, trauma informed interviews.  

Throughout his career, Kevin has been involved in preparing for litigation in state and federal courts, before administrative agencies and before arbitrators.  With decades of experience and a deep understanding of how to conduct a balanced, thorough, credible investigation, Kevin is uniquely suited to advise senior leadership on how to respond to complaints about conduct.  His track record of success includes the supervision of high-stakes investigations which produced effective and reliable results.

Kevin has extensive labor relations experience. He was an advocate in grievance arbitrations regarding disciplinary and contract interpretation issues. Kevin negotiated collective bargaining agreements in the public and private sector, in a wide range of industries.

Kevin received his B.A. in Political Science, magna cum laude from Tufts University, and his J.D, with honors, from the University of Connecticut School of Law.  He is admitted to practice in Massachusetts, New Hampshire and Connecticut.  Kevin is a member of the Labor and Employment Sections of the New Hampshire Bar Association and the American Bar Association.   Kevin is also member of the Boston Bar Association College and Universities section and a former member of the National Association of College and University Attorneys.

Kevin is physically based in New Hampshire. He regularly conducts investigations throughout New England.