Steven O'Brien

Steven O'Brien is an accomplished sales professional with extensive experience in enterprise sales and client advisory roles. Currently serving as Enterprise Sales Director at Five9 since June 2025, O'Brien focuses on CcaaS and UC solutions, as well as AI and automation. Previous roles include Enterprise Account Executive - Solution Specialist at T-Mobile and Sr. Sales Director at Wilmac, where O'Brien emphasized customer success and lead qualification. O'Brien also held the position of Account Executive at LiveVox, and served as President and CEO of Cheese Masters, Inc., which launched New York's first quick-service grilled cheese restaurant franchise. O'Brien holds a degree in Business Administration with concentrations in Entrepreneurship and Marketing from Northeastern University.