Boswell steps into the CEO role after nearly seven years at PlayVS, most recently serving as Chief Technology Officer since January 2025 and previously leading the company’s engineering, product, and operations organizations. He is a proven technology leader with 23 years of experience and three successful exits as an executive. Before PlayVS, Boswell served as CTO of education technology company ArborBridge, where he designed and built its global online SAT and ACT tutoring platform and oversaw the acquisition of College Planner Pro. ArborBridge was later acquired in 2021.

Jonathan graduated from Florida State University and resides in Los Angeles.