Building Disney+, ESPN+ and a New SiriusXM

He started tinkering with computers in elementary school. Using an old IBM machine his grandfather passed down to his family, Wolinsky learned Visual Basic—an early programming language developed by Microsoft for Windows.

At first, he built apps to play pranks on his friends through AOL’s messaging platform. 

“I had a little mischievous streak at the time,” he said, laughing. “It was never anything nefarious—just doing the things that would sound fun for a middle schooler.” 

But his love for coding grew into something bigger. He sought resources to develop his skills and found like-minded people in school. By the time he got to the University of Maryland, he chose to major in computer science and then joined the QUEST Honors Program, where he sharpened his skills at the intersection of technology and business. 

“I thought maybe I would start a company or work on the business side in some way, so I just wanted exposure to that,” Wolinsky said. “The collaboration between the business school and computer science really appealed to me.” 

Now, Wolinsky is living out his childhood dream as the group vice president of software engineering for the experience engineering group at SiriusXM, whose automotive app is available on over 80% of new cars sold in the United States. He leads engineering for the listener experience across SiriusXM and Pandora, spanning mobile, web, connected devices and the next-generation in-vehicle app. His team develops the app’s functionality for playback, browsing, search, personalization and everything else related to a user’s listening experience.

“I’m really happy with where I am at the moment,” Wolinsky said. “I just want to continue working on really high-leverage, interesting consumer products.”

Before arriving at SiriusXM, Wolinsky worked at MLB Advanced Media, where he helped build a platform for fans to stream baseball games. That platform also hosted NHL games, Major League Soccer games, Eurosport, HBO Now, Sony PlayStation Vue and other direct-to-consumer video streaming products. As a content engineer, Wolinsky worked with a team on the back end to configure the content pipeline and content catalog. Their system allowed the platform to pull metadata and artwork to inform how users manage, curate, search and discover content. 

The technology eventually became the foundation of BAMTech, a streaming technology company spun out of MLB Advanced Media. Disney acquired a minority stake in 2016 and later took majority ownership, rebranding the organization as Disney Streaming Services. At BAMTech and later Disney Streaming, Wolinsky and his teams helped build the technology behind ESPN+ and Disney+. 

“That was definitely one of the highlights of my career,” Wolinsky said. 

Then in 2022, Wolinsky joined SiriusXM for the opportunity to apply what he learned building large-scale streaming products to another well-known consumer entertainment brand. As a longtime SiriusXM and Pandora listener, the opportunity was especially appealing. He joined SiriusXM as vice president of platform engineering, helping build the technology foundation and developer platforms used by the company’s engineering teams. He then became vice president of software engineering, leading the backend services platform, and finally reached his current role as group vice president responsible for experience engineering. 

Day to day, Wolinsky is “in one big meeting,” he jokes. He spends much of his time on organizational design, people leadership, technology strategy and long-term planning. Much to the chagrin of his middle school self, he does almost no computer programming. Still, he sees similarities between his developer roles and his current leadership role. 

“I consider myself an organizational engineer,” he said. “I love figuring out the perfect way that our team should be structured to set us up for success. It is a little bit like software engineering—fitting the pieces in the right place.”

In part, he credits his experiences at UMD and in QUEST for preparing him for success at the intersection of entrepreneurship, technology and business. For QUEST’s capstone projects, students work on interdisciplinary teams solving projects for real-world companies. 

“The entrepreneurial aspect and real-world application really did it for me. I really liked the idea of working with actual clients and seeing how the stuff that we were learning in class applied,” he said. “I also think that being part of a team serving a real client in a semi-real environment sets you up for industry better than going straight from the classroom.” 

And as much as Wolinsky misses coding, he gets as much satisfaction leading teams as he did developing software himself.  

“The thrill of creating something is pretty apparent to anybody who's done it. Seeing working software take shape after it was just an idea in your mind—there’s nothing like that. It's why anyone who builds things for a career gets into it,” Wolinsky said. “But there's something equally satisfying about seeing your team deliver something amazing that you had almost no part in actually building yourself. That you were responsible for setting the conditions that made it possible for that to happen. That brings a different type of satisfaction.” 

—Story by CMNS