Reginald Matthews

Reginald Matthews, J.D. is an Atlanta-based entertainment, sports, and technology law professional with several years of experience in America and abroad. His day-to-day consists of being a member of the legal team at Calendly, LLC, where he negotiates an array of agreements from master service agreements, data processing agreements, trademark, copyright, and licensing agreements, and a host of other agreements. Reginald also supports numerous functions of the Calendly organization, from marketing, communications, engagement, customer support, sales, engineering, product, and people.

Before joining Calendly, Reginald was a law clerk at Crespo Law. His experience included contract negotiations, trademark and copyright formation, business and entity formation, and other business needs for Atlanta and New York athletes, entertainers, politicians, and other public figures.  

Reginald is deeply involved in his community. He is currently a board member of the Atlanta-based non-profit Page Turners Make Great Learners. This literacy organization motivates and encourages students to read through various supplemental experiences that support and reinforce the classroom curriculum. Reginald is also a DEIB advocate focusing on creating workplaces promoting connection, inclusivity, allyship, and belonging across teams and time zones. He is currently a subcommittee co-chair within the Black Belonging Group focused on ensuring an equitable experience for diverse employees within Calendly. He continues to promote diversity, equity, and inclusion in the legal field by providing opportunities for lawyers within tech, mentoring future and current law students, and working to increase the diversity pipeline for college and law students looking to enter the intellectual property, entertainment, sports, and tech fields. Reginald has had the opportunity to speak on and moderate several panels and symposiums for Morehouse College, Southern University, MentorMeCollective, Candid Conversations with Calendly, and a host of other organizations.

Reginald has partnered with Southern University Law Center's Sports and Entertainment Program to establish a certification program and to provide opportunities, training, and development to law students and professionals to mold the next generation of sports and entertainment professionals. He is a foundering alum of the Southern University Law Center Sports and Entertainment Symposium, where notable thought leaders and public figures such as T.I., Melissa Proctor, Randell Gay, Kevin Liles, and David and Lyn Talbert; and he has moderated discussions with Sony, Viacom, BET, BNC, Pixar, Diverse Representation and other entertainment organization. Reginald is currently working on curating the Southern University Law Center Tech Law Program.

Reginald has been featured in several publications, including VoyagerATL, ShoutoutATL, The Playbook 2019 and 2020, and The SCREAMM Project. In 2022, Reginald was featured on InView Legal Magazine's cover. The cover story "No one wants to work with a book" focuses on the struggles of breaking the traditional mold of what everyone thinks a lawyer is and being true to yourself while in the legal industry. He has also talked about working in-house and how effective communications across the business only make you a better legal professional.

A native of Detroit, Michigan, Reginald is a graduate of Morehouse College, with a B.A. in Political Science with a concentration in American Government and Politics and Southern University Law Center (J.D.), where he focused on Transactional and Intellectual Property Law.