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Robert Fleischacker has a long and varied career in the legal field. Robert started their career in 1988 as Division Counsel, Legal Counsel, and Attorney. Robert then moved on to Pentair Water Quality Systems in 1996 as Assistant General Counsel. Robert then joined Stoughton Trailers, LLC in 1998 as General Counsel & Secretary. In 2009, they became Vice President, General Counsel & Chief Compliance Officer at The Remi Group (Remi) where they created and implemented the company's first legal and compliance department and developed policies and procedures. In 2019, Robert joined Passport as Assistant General Counsel. In 2018, they became General Counsel at Root Level Technology. Most recently, Robert joined EVC Ventures in 2022 as Chief Legal Officer.

Robert Fleischacker obtained a Bachelor of Science (B.S.) in Economics from the University of Wisconsin-Madison between 1980 and 1984. Robert then attended the California Western School of Law from 1985 to 1987, where they earned a Doctor of Law (J.D.) degree. In September 1988, Robert obtained a license to practice law in Wisconsin from the State Bar of Wisconsin. Robert then obtained a license to practice law in North Carolina from the State Bar of North Carolina in June 2011.