PlayOn! Sports Appoints New CFO – ON Partners

Jan 30, 2024

PlayOn! Sports Announces James Rosenstock as Chief Financial Officer

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ATLANTA /PRNewswire/ — PlayOn! Sports, a leading high school media and technology company, announced the appointment of James “Jay” Rosenstock as Chief Financial Officer (CFO).

Rosenstock is an accomplished media and technology executive who has previously served as CFO at Skillshare, a market-leading direct-to-consumer (DTC) creative learning marketplace, and ezCater, a top business-to-business (B2B) online catering marketplace. At PlayOn!, Rosenstock will oversee the Accounting, Finance, Tax, M&A, Information Technology and Security and Project Management Office (PMO) departments.

“We are thrilled to welcome Jay to the PlayOn! leadership team. He brings extensive experience in both the DTC and B2B industries and has guided leading companies through significant transformation,” said David Rudolph, PlayOn! founder and CEO. “We are confident that Jay’s expertise will be valuable as we continue to innovate for the benefit of schools and fans nationwide.”

“As the child of two educators and an avid sports player and youth coach, it’s a privilege to join such an innovative company and accomplished leadership team as we embark on the next stage of growth,” said Rosenstock. “I look forward to the journey ahead as we continue to scale our business and create meaningful experiences for schools and communities across the country.”

Earlier, Rosenstock was instrumental in architecting and operating Discovery’s international businesses, where he oversaw Discovery Education International. He also held leadership roles with SONY, WWE and VICE. Rosenstock began his career as an investment banker covering the Technology, Media and Telecom (TMT) sector. He is an honors graduate of Virginia Tech, where he serves on the Virginia Tech Foundation Board of Directors. Rosenstock is also a long-standing member of the Board of Directors for Special Olympics New York.

“Jay is a forward-thinking executive who values the power that sports have to impact not only the lives of our young people but also their families, schools and communities,” said Special Olympics New York President & CEO Stacey Hengsterman. “Jay’s leadership will be an incredible asset to PlayOn!, just as it has been for our statewide nonprofit.”

View the full press release here.

Executive Search Partnership: PlayOn! Sports

ON Partners partners Tara Flickinger and Matt Mooney are proud to have partnered with PlayOn! Sports on this CFO search. Learn more about ON Partners by downloading our recent Variance Report, which explores four executive hiring trends of 2023, and our Talent Intelligence Report, where we open up on our data innovation and research, offering a fresh perspective on executive hiring.

The future of high school athletics and activities is powered by PlayOn! Sports. Through the NFHS Network, GoFan and rSchoolToday, the PlayOn! team elevates the event experience for schools and fans across streaming, digital ticketing, scheduling and sports management. For more information, visit

To learn more about partnering with our executive search firm, meet our executive search consultants.

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