Woodruff had worked as the 10 p.m. weeknight anchor for Newsline 9 in Wausau, Wisconsin. Prior to joining WAOW, Woodruff spent two years as a reporter and fill-in anchor at WFFT FOX Fort Wayne in Fort Wayne, Indiana. He contributed to two Emmy nominations for Best Newscast as well as a First Place award for Best Newscast from Indiana's Society of Professional Journalists.
While at BYU, Woodruff worked as a reporter, anchor, and producer for the BYU Daily News. He also reported for BYU Weekly. He completed news internships at CNN (Washington, D.C. bureau) and KSL-TV. He also interned with the Utah State Legislature and was involved in international development work in Ukraine.