Caldwell won her first World Cup aerials event in the United States in Lake Placid, New York, in January 2011, becoming the youngest freestyle female ever to win.

Upon returning, she claimed the silver medal at her first world cup event in China, earning a spot to the 2014 Winter Olympics in Sochi, Russia.

She competed again in Beijing in December 2014, winning gold, alongside her 19-year-old teammate Kiley McKinnon, who won silver.

[1] She became the first female skier to land a quadruple twisting triple back flip at the 2017 World Championship in Sierra Nevada, Spain.

Her family now resides in Houston, Texas, and she lived in Hamilton, Virginia,[3] and then in Park City, Utah, beginning around 2013.