In a box overlooking the field, two officials scrutinize the catch, rewinding the tape again and again in their tiny room. Two others — a woman, whose trigger finger captures every single play with the click of a button, and a “communicator,” an NFL employee with a direct line to the field — accompany them. Within the final two minutes of either half, this foursome calls challenges, rather than the competing team’s coaches. And in this case, they call one. Immediately, the on-field officials blow their whistles, stop the game, and duck under the instant replay hood behind the sidelines.

On a massive screen in the National Football League’s Officiating Command Center in New York City, I’m watching them watch the scene play out. The game isn’t live, but the center’s Big Brother feel is undeniable. In this room a team of ex-officials grades the nine referees’ (seven on-field and two in the booth) officiating of every game — and the officials with the best marks head to the playoffs. The Command Center also hosts data, everything from penalties to announcer comments to more traditional playtime statistics, and stores it in its Game Statistics and Information System (GSIS). The media, fans, and NFL execs consume that data in all sorts of ways — and the system’s existence is one indication of the League’s push to increase its digital footprint.

Another: the NFL’s first-ever Chief Information Officer Michelle McKenna-Doyle. After CIO stints at Universal Orlando Resort and Constellation Energy, she was hired last September and slowly acclimated herself with the NFL’s complex model — “We’re really a trade association with [32 teams, or] operating businesses,” she explains — and forged relationships with her fellow executives, owners, and sponsors to appease resistance to the systems she planned to implement.

Wireless, for instance, was initially an uphill battle. A year or two ago, McKenna-Doyle explains, there was pushback from certain clubs claiming fans watching the game live didn’t really want Wi-Fi. McKenna-Doyle helped the Philadelphia Eagles offer free wireless throughout its stadium and negotiate communications deals. Buzz around its new offerings proved the old theories wrong. Clubs now believe in Wi-Fi “just like having water and electricity. You just have to have it,” she says.

Though all 31 NFL stadiums have Wi-Fi on the sidelines, the high-density consumption of data presents challenges. McKenna-Doyle works with clubs and their telecom and Wi-Fi providers to craft personalized solutions based on the stadiums’ various needs. “To make sure the game is pulled off flawlessly, we have to make sure communication is flowing from the sidelines in a way that’s uninterrupted.” Currently, communication systems among officials, coaches and players, doctors, are in different silos, and very little cross-communication occurs. Next game, look for the guys in colored hats, and you’ll have some idea of how the different communication channels work: Yellow oversees coach-to-coach and coach-to-player communications; orange handles Wi-Fi frequency; green works with the NFL and its TV partner on broadcasting the game; red is the airway management physician, helping with players’ respiratory issues. McKenna-Doyle hopes to restructure the system for more holistic communication and decrease the throng of techies by the bench.

NFL Media COO Brian Rolapp focuses on how players’ moments, in plays big and small, can enhance fans’ at-home experience. The media partnerships and brands like Fantasy Football and RedZone are Rolapp’s babies. He and McKenna-Doyle work hand-in-hand to ensure each platform delivers the greatest goods possible. The two currently are developing Next Generation Statistics. This new approach will focus on player tracking — their locations, their speed — through chips in their shoulder pads. Next Gen Stats won’t replace the NFL’s current statistics capture until the ball, the sidelines, the down markers, and other aspects of the game can be equally measured; but in its first phase, the stats will benefit fans’ and the media’s experience. Eventually, McKenna-Doyle hopes to evolve the NFL’s current data model; Next Gen Stats will give the League a competitive edge against other outlets, like ESPN, measuring game data with their eyes.

Unsurprisingly, the sidelines host much tougher customers than the stands or at-home fans. Coaches and players challenge many of McKenna-Doyle’s implementation plans. This past year, she rolled out Electronic Medical Records with eight teams. Next year, the remaining 24 will make the switch. Microsoft sponsors the tablets and their software — a deal headed by Rolapp — and the contract is covered in McKenna-Doyle’s fingerprints. Doctors can quickly access players’ medical histories, and can rewatch tackles that caused injuries through a replay system called Injury Review Video to better understand treatment of a tear or dislocation. Eventually, McKenna-Doyle hopes to have the Surface tablets used similarly for game strategy and play analysis. But the competition committee won’t approve such a rollout unless every club participates, and the coaches worry about security and the devices lagging or failing during game time.

McKenna-Doyle thinks of herself as a technologist who looks at the business side of things first. “Frankly, solving the technology is the easy part,” she claims. “I’m glad we had a purpose other than game strategy to test [tablets] on because if it goes down or there’s an issue or communication interruption, it’s not affecting calling of plays.”

And as for Kerley’s questionable in-bounds catch? After an official review, it’s confirmed he was out of bounds, playing in those sidelines McKenna-Doyle is working to reshape.

A shorter version of this story appeared in the December 09, 2013 issue of Fortune.