James Aylward

James Aylward is a seasoned professional in customer success and project management with extensive experience in the media and technology sectors. Currently serving as a Senior Engagement Manager at Whip Media since February 2025, Aylward previously held a notable role as Director of Customer Success at FreeWheel, where strategic relationships with high-profile clients were cultivated and technical solutions aligned with client visions. Additionally, Aylward directed client technology initiatives as Program Director, ensuring program alignment with business goals. Prior experience includes a Project Manager position at HBO, overseeing cross-functional teams to launch content globally across multiple platforms. Aylward holds an MBA from Baruch College and a BA in Liberal Arts and Sciences from The Evergreen State College, along with educational experiences in Spain and Mexico.