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Olivia Bolles has a diverse work experience spanning several industries. Olivia is currently employed as an Ecommerce Manager at Living Proof, Inc. since March 2021. Prior to this, they worked at Wayfair from January 2018 to March 2021, holding various roles including Senior Category Associate, Category Associate, and Buyer for Perigold. From May 2017 to June 2018, Olivia worked as a Marketing Assistant at Jen Groover/ Groover Media/ JumpStart Connect. Olivia also gained coaching experience at Connecticut Elite Field Hockey Camp, where they worked as a Coach from July 2015 to July 2017. Additionally, they were a Student Athlete at the University of Connecticut from 2013 to May 2017. Olivia's work history also includes a brief internship as a Promotions Intern at WMGK Greater Media Philadelphia in June 2016.

Olivia Bolles earned a Bachelor's Degree in Communication, General from the University of Connecticut, where they studied from 2013 to 2017.