Benchmark AI Chases $45M in College Sports. It Reads the Contracts Nobody Reads. Athletic Directors Are Listening.
AI startup Benchmark, founded by Michael Anthony, is helping college athletic departments compare contracts, cut costs, and prepare for a revenue-sharing era estimated at $45 million. The tool evolved from an earlier platform called Win AD, which aggregated coaches' contracts and vendor data. Bubba Cunningham, 2020 Under Armour/NACDA Athletics Director of the Year and now senior adviser to the chancellor at North Carolina, told USA TODAY Sports that the platform mushroomed to cover multimedia rights, shoe company agreements, and essentially anything the department contracts for.
The mechanism here is contract aggregation at scale. When an organization signs dozens of vendor agreements across multiple departments, no single human holds the full picture. AI solves this by ingesting every contract, normalizing the terms, and surfacing comparisons that would take a legal team weeks to assemble manually. The mental model is information asymmetry correction: the party with the most complete data wins the negotiation, and Benchmark is selling that asymmetry to athletic departments.
Benchmark, founded by Michael Anthony, son of John Anthony whose travel company serves college athletics programs. Users include North Carolina, where senior adviser Bubba Cunningham and staff utilize the tool regularly for coaching contracts and vendor agreements, per USA TODAY Sports.
- Gather three recent contracts or subscription agreements you have personally signed. This could be a gym membership, a streaming service, or a phone plan. Expected outcome: you will have a small set of documents to compare.
- Upload each document to a consumer AI tool such as ChatGPT or Claude and ask it to extract key terms: cancellation policy, auto-renewal, monthly cost, and penalty fees. Expected outcome: the AI will produce a structured summary of each contract in seconds.
- Ask the AI to create a comparison table across all three contracts, highlighting which has the most favorable terms and where you are overpaying. Expected outcome: you will see the same contract aggregation principle Benchmark applies to athletic departments, demonstrated on your own finances.