Ballerina turned gallerina, Olivia began her career in music and ballet. She trained and competed in classical piano, violin, and voice, and studied dance with American Ballet Theatre, Oregon Ballet Theatre, and Ballet West. After retiring from ballet early, she expanded her creative practice as a sign artist, producing large-scale lettering, drawings, and paintings for retail spaces, and founded an online art magazine during COVID, where she interviewed artists and built a digital platform.

Since 2021, Olivia has been working at Gagosian Gallery in Beverly Hills, contributing to numerous major exhibitions, including the Jean-Michel Basquiat exhibition, Made on Market Street, and at least 30 others. She works in sales and seeks to create a more welcoming entry point into collecting, with the belief that art should feel accessible.