Carlyle Massey

Carlyle Massey serves as the Senior Director of Customer Operations & Support at CarGurus since September 2022. Prior experience includes the role of Director of Customer Solutions at Plymouth Rock Assurance from April 2021 to August 2022, and a significant tenure at Liberty Mutual Insurance from 2012 to 2020, where responsibilities included leading a 120-person department through transformation and providing strategic leadership to a 1,500+ employee Claims Support Operations. Carlyle's career began at Wayfair, where operational management of the call center and workforce management were key roles. Educational qualifications include an MBA in Business Administration and Management from UW Foster School of Business and a B.A. in English and Psychology from Williams College.