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E. Jack Connolly's work experience begins in 2010 as a Judicial Intern for the Honorable Judge Robert W. Pratt in the Federal Judiciary. In 2011, they worked as a Summer Associate at Ahlers & Cooney, P.C. From 2012 to 2015, Connolly served as a Contracts Counsel and then as an Assistant General Counsel at Workiva. In 2018, they joined DHI Group, Inc. as a Corporate Attorney, later becoming a Senior Corporate Attorney. In 2022, Connolly was promoted to Vice President, Legal, and in 2023, they assumed the position of Vice President & General Counsel at DHI Group, Inc.

E. Jack Connolly earned a Bachelor of Arts degree in Political Science from the University of Iowa in 2009. E. Jack went on to complete their Juris Doctor degree in Law from Drake University Law School in 2012.