Saylor grew up in Woodland, Utah, trying every sport she could. At age four, she found skiing and immediately fell in love. She met Picabo Street before deciding to attend her academy, and O'Brien credits Picabo as significantly influencing her skiing and who she wants to be as an athlete and person. O’Brien joined the Stifel U.S. Para Alpine Ski Team in 2022 and had a successful first season on the circuit. The 2024-25 season was one to remember, when O'Brien landed on the World Cup podium multiple times as well as earning her first World Cup win. When she isn’t skiing, you can probably find her dying or cutting her hair, making lots of art, going to concerts, and hanging out with her dog.