Fastbreak AI Is A Scheduling Power Play

No professional or amateur sports schedule will please all players, fans and stakeholders. A well-orchestrated schedule should rankle the feathers of all relevant constituencies equally—in there lies the challenge.

“Scheduling in general is the art of equally managing disappointment. You want to make sure everybody equally hates you—then you’ve done a good job. If one team thinks ‘oh my God, this is amazing, this is fantastic’ then you’ve probably done something wrong,” explains Fastbreak AI CEO John Stewart.

Stewart, a serial entrepreneur based in Charlotte, North Carolina, made his mark with MapAnything—a location intelligence and route optimization system run on Salesforce’s platform. Features included territory management, multi-day route planning, and location-based workflows to enhance field operations. Under his leadership, MapAnything grew to $22 million in annual recurring revenue before being acquired by the customer relationship management behemoth itself in 2019 for $250 million. Its DNA still powers what is now known as Salesforce Maps.

Following the sale, Stewart was bound by a three-year non-compete that kept him out of the scheduling space. Since that’s his forte, he used the time to reset before plotting his next move. Like many temporarily sidelined tech impresarios, he invested in startups, dabbled in rental properties, sat on boards, mentored and took on occasional consulting work.

Harnessing AI to build out schedules for leagues–condenses a grind of a process that could take weeks to finish tweaking into just a few hours. Fastbreak AI has become a pro sports scheduling goliath. When your client roster includes dozens of professional sports leagues—like the NBA, WNBA, NHL, MLS, Serie A and Premiership Rugby—it’s clear the industry has taken notice.

At the core of Fastbreak’s platform is an algorithm that weighs dozens of variables—venue availability, player rest, travel, broadcast windows—and adapts to whatever constraints a league values most, whether that’s competitive balance, minimizing back-to-backs, or boosting TV ratings.

“We are sort of the 800 lb gorilla,” Stewart said. “I don’t have to convince you to use Microsoft Office. Here’s the validation: there are twelve or thirteen people in the world that really understand this stuff, in terms of the optimization that applies to sports scheduling and ten of them work for us. We have a density of expertise and the fact that we are so broad in our customer base gives us a unique ability to digest new problems that we see. Every league has a unique problem.”

The company, now the dominant player in the space, has been on an acquisition spree of late—bringing four companies into the fold in the past six months, an effort that has substantially expanded its footprint, with its software now scheduling 55 professional sports leagues.

Tiger Woods and Rory McIlroy-backed TMRW Sports is a recent client—and also an investor—onboarding the tech after TGL’s inaugural season schedule was already set. But they will be using it moving forward to create a schedule for next season that balances optimal broadcast viewership with player availability.

Solving TGL’s Scheduling Headache

Most pro sports teams travel together and follow a predictable cadence of home and away games. But TGL presented an entirely different challenge. In professional golf, players build their own tournament calendars—and in a league where team matchups, TV broadcasts, and individual preferences all have to align, Fastbreak AI faced a complex puzzle.

“They have their teams, but every one of those golfers has an independent and different schedule. There’s a schedule of broadcasts they have to meet, a schedule of match play for their teams and they have to accommodate the individual schedules of the players on the six teams,” Stewart explained.

Most of Fastbreak AI’s remaining competitors are consultants, some of whom rely on third-party optimization engines like Gurobi or Xpress. Stewart’s co-founders, Dr. Chris Groer and Dr. Tim Carnes are data science and mathematical optimization experts who previously worked on the NBA’s scheduling system while at KPMG, when the league contracted the firm to build an in-house scheduling solution. Stewart had initially recruited them to work on MapAnything, and when Fastbreak AI launched, one of the first calls they made was to their old pals at the NBA.

At the time, the league was developing the concept for its in-season tournament—a scenario that pushed the limits of their existing scheduling software and gave Fastbreak AI an opportunity to showcase the capabilities of its platform’s custom repair algorithm.

“It was pretty obvious they were going to be a customer and they wanted to be on our cap table,” Stewart said. “So, we opened up a small friends and family round. Then in May of 2023 we actually launched the software platform—so for two years now the platform has been on the marketplace,” Stewart said.

Future Functionalities

Play simulation is an area Stewart’s team has been contemplating exploring—looking at player tendencies to then make assumptions on match length.

“We don’t currently do that, we are looking at it to see how it would apply. This is a huge problem in any type of combat sport. They are always behind schedule and athletes never know when to show up because a match can be over in fifteen seconds or it could take six minutes,” Stewart explained.

Simulations could even be used to potentially juice the PGA Tour’s pace of play, a perennial pain point. Theoretically, if certain players tend to play a few minutes slower depending on their pairing, an algorithm could solve for that—generating more efficient groupings, at least in pre-cut rounds before performance determines the tee sheet.

“It’s definitely possible, there is a math problem to be solved there and we’ve thought about how it could be applied to any math-based sport.”

Same Engine, Different Leagues

Predictive viewership is another area Fastbreak AI is plowing ahead on. They have a product coming out later this year that models for eyeballs as a schedule optimization variable.

“This then has an impact on the value of media rights and of course that is the way we are looking on it as well,” Stewart said.

Fastbreak AI’s professional contracts help subsidize the development of its scheduling engine, which is then applied across both pro and youth sports.

“The media rights deal of the NBA is not the same as the Greek Basketball League—both of which are customers—but it’s exactly the same platform,” Stewart said.

The company adjusts its pricing model based on the rights package value of each league, effectively tethering service costs to the revenue potential of what clients are selling to broadcasters.

“We will bring our capabilities to the youth level to make it more efficient and a better experience for the parents. We are doing a whole sports approach, from the grassroots to professional leagues using the same technology,” Stewart said. He would know—Stewart has five kids and has logged plenty of hours navigating the chaos of youth travel sports firsthand.