Cailee is from Mayville, North Dakota where she attended May-Port CG High School. She was an all-state athlete all four years in both cross country and track, and won state championships in the 1600m, 3200m and cross country. She competed in six events at the state meet (4x200, 4x400, 4x800, 800m, 1600m, and 3200m). Her high school personal bests included 5:08 in the 1600m and 11:14 in the 3200m, both of which also set school records.
 
After graduating in 2017, Cailee attended South Dakota State University, where she double-majored in Ecology/Environmental Science and Wildlife and Fisheries  Sciences. At SDSU, she set a school record of 4:46 in the mile, won two Summit League Championships, and competed at NCAA DI East Regionals in the 1500m. After SDSU, Cailee used a final year of eligibility at the University of Minnesota-Duluth, where she earned a post-baccalaureate certificate in Environmental Education. On the oval, she was the runner-up at the NCAA DII Indoor Championships in the mile, and placed 4th in the 1500m at the Outdoor Championships. In addition, she won two NSIC Conference Championships. She finished her collegiate years with personal bests of 2:07 (800m), 4:19 (1500m), 4:46 (mile), and 9:35 (3000m).
 
In her first post-collegiate race, Cailee won the Wisco Mile, setting a meet record and personal best of 4:43. She joined Minnesota Distance Elite in August of 2023.