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Rob served as a senior leader within the Wisconsin Senate under five majority leaders, three Republicans and two Democrats. As chief clerk and director of operations of the Wisconsin Senate, Rob was the parliamentarian of the Senate and was responsible for the proper, constitutional functioning of the Senate as a lawmaking and oversight body within state government. Each time he stood for the position he was unanimously elected by the Senate. Prior to being chief clerk, Rob was a legislative drafting attorney, specializing in business and corporate law, campaign finance, election law, economic development law, and construction law.

Rob also served as deputy secretary of the Wisconsin Department of Employee Trust Funds, the executive branch agency charged with administering the Wisconsin Retirement System and the purchasing and provision of health insurance benefits for state and other public employees. In this role, he oversaw all aspects of day-to-day operations and ensured regular and appropriate coordination of efforts between the agency and the governor’s administration.