When I first connected with Jack Adler, he was still a pretty fresh college graduate of Syracuse (as a fellow alum, I’m obligated to obnoxiously shout “Go ’Cuse!”), setting the foundation for his athlete marketing platform, Out2Win.
Well, a lot has changed for him and his startup in the last couple years. Out2Win has grown from a headcount of three in 2024 to nine now, and also has a new HQ in New York City, working with brands like Amazon, Nike and Under Armour in that time “that have really helped shape the trajectory of the business,” Adler told me recently.
Most notably, Out2Win has shifted from a marketing SaaS platform to an agency-like firm that uses its tech layer to boost the speed and efficiency of its work. Adler and crew built a proprietary algorithm that could gauge and identify the right athletes for brands to partner with across social media/influencer campaigns. But now that technology is a component of the startup’s Autopilot feature, which debuted late last month.
The way it works: a brand can build a campaign by entering the desired components of that effort. Autopilot takes the hoped-for result (awareness, more traffic, etc.), the budget and the type of athletes they’re looking for, etc., and launches the campaign.
It’s worth noting that we’ve seen other companies in the space, like OpenSponsorship and Parity, find real success by providing a hands-on agency approach in brokering the relationships between brands and athletes. Out2Win’s database of 300,000 athletes to find ideal matches for brands produces contracts for the athletes, creates content briefs, and handles the paid-media efforts.
“We have an agent that goes and conducts the outreach directly to the talent and builds out the campaign, all with human interjection,” Adler said. “We have a team that will be managing the account, but it allows us to just go scale our business in the way that we would a software, but with the outcome delivery of an agency.”
This Autopilot tool enables Out2Win to support clients now with multiple offerings. Its self-service foundation is still available for a client to dig into partnership opportunities on their own, but now this injection of agentic AI helps Out2Win act as an AI native agency that can oversee the collaboration as well, Adler added.
This year alone, Out2Win has helped Amazon and probiotic soda brand Olipop collaborate on a March Madness campaign with 12 athletes across the men’s and women’s tournaments. And with this new AI component, Adler has already seen a compelling use case with drink producer Accelerator Active Energy, which used Autopilot for a social campaign that produced the company’s best sales week on Amazon in 2026. It’s early proof that the new feature is immediately answering a need.
“To be honest, we always had minimalistic layers of AI involved. The Out 2Win score, that proprietary algorithm [that rates product-athlete fit and an athlete’s social media effectiveness], has features of AI involved in it,” Adler said. “But I never thought that we’d be at a point of today, which is where AI is literally an integral part of the actual delivery of the service.”
