Matthew Massey

An entrepreneurial and solutions-focused legal advisor, Matthew has 15 years of in-house experience, having counseled and led initiatives for a VC-backed, high growth startup as well as large public companies. Most recently, Matthew was Deputy General Counsel for Root Insurance, where he helped the legal department grow and keep pace with Root’s tremendous pace, ultimately culminating in an initial public offering in October 2020. As Deputy General Counsel, Matthew was the company’s lead commercial counsel, while overseeing the department’s work for business development, marketing, intellectual property, real estate, and data science. Additionally, Matthew served as a trusted advisor and contributor to the management team and board of directors.

Throughout his 20 years of legal experience, Matthew has served in various roles for large international companies and closely-held private companies, including JPMorgan Chase Bank, The Scotts Miracle-Gro Company, and System, Inc. Matthew holds a B.A. in philosophy from Boston College and a J.D. from the Wake Forest University School of Law.