Cailee is from Mayville, North Dakota where she was a prolific athlete at May-Port CG High School. She was an all-state runner all four years in both cross country and track, and won state championships in the 1600m, 3200m, and cross country. 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. As a Jackrabbit, 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. After joining Minnesota Distance Elite in August of 2023 she has managed consistent improvement in all distances raced. She was second in the Ryan Shay road mile in 2024 with a time of 4:26.2 and managed to drop her 1600 meter time by almost 20 seconds throughout the 2024 and 2025 track seasons. Her best performance was at the 2025 Stumptown Twilight meet (4:10.81), which qualified her to compete at the 2025 USATF Outdoor Track and Field Championships. She will continue to push herself on the track in the middle distances in the seasons to come.