Before becoming an attorney, Dean Stewart spent fifteen years working as a teacher and administrator for the Cache County School District in Utah. She obtained her undergraduate degree in English and master's degree in educational leadership from Utah State University. While working on her master's degree, she took a class titled "Legal Issues in Education" that provided the original spark for her interest in attending law school.
During Dean Stewart's time as a BYU Law student, she was the managing editor of administration for the BYU Law Review and the President of Women in Law. Following graduation, Dean Stewart continued her efforts to promote opportunities for women in the legal profession as a a member of the board of the Women Lawyers of Utah.
Dean Stewart clerked for the Honorable Judge Andrew J. Kleinfeld of the U.S. Court of Appeals for the Ninth Circuit in Fairbanks, Alaska, and then for the Honorable Judge Ted Stewart of the U.S. District Court for the District of Utah in Salt Lake City. She then entered private practice in the commercial real estate section of Parr Brown Gee & Loveless in Salt Lake City.