Gentry started her career as a running coach in the United Kingdom and became a Nike+ Run Club Coach in London. Gentry moved to New York City in 2019 to join Peloton as a Tread specialist. Together with Robin Arzon, she developed an 18-week marathon training program for the Peloton app. In this role, she has become a globally recognized trainer and face of the Peloton brand, partnering on initiatives with celebrities including Ashton Kutcher.