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Jason Penta's work experience begins in 2003 as an Intern at Cartus (formerly Cendant Mobility). From 2005 to 2010, they held multiple roles at Venture Direct Worldwide / PlattForm Advertising, including Media Buyer/Planner, Senior Search Marketing Coordinator, Publisher Relations Manager, and Vice President, Marketing. In 2010, they became Vice President Client Services at Pontiflex, later renamed Crossboard Mobile. Jason then transitioned to Vice President, Media Operations before leaving in 2014. In 2015, they worked as a Consultant in Product & Business Development at Prospectiv before joining HomeServe USA. At HomeServe USA, they held various director-level positions, including Director of Energy Services & New Ventures, Director of Product Management, Director of HVAC & Strategic Initiatives, and most recently, Senior Director of HVAC Marketing.

Jason Penta completed their Bachelor's degree in Business Administration (Marketing) from Marist College from 2001 to 2005.