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Billy Wailand has a solid background in corporate development and law. Billy started at GCI Communication Corp. in 2014 as an Associate General Counsel, where they led in-house counsel on various M&A deals and commercial litigation cases. Billy also played a key role in developing and implementing the company's corporate compliance program. In 2019, they were promoted to VP, Corporate Development, and in 2021, they became the SVP, Corporate Development at the same company. Prior to their time at GCI, Billy was a Partner at Feldman Orlansky & Sanders from 2010 to 2013. Billy also gained valuable experience as a Law Clerk for Honorable Dana Fabe at the Alaska Supreme Court and Honorable Richard J. Holwell at the United States District Court, Southern District of New York. Billy started their career as an Associate at Debevoise & Plimpton in 2007.

Billy Wailand graduated from Harvard University in 2002 with a Bachelor of Arts (BA) degree in Environmental Science & Public Policy. Billy then went on to pursue a Doctor of Law (JD) degree from New York University School of Law, where they completed their studies in 2006.