Uber was a pioneer in seamlessly connecting passengers and drivers through an app. Now a union-led group meant to represent its drivers is also taking an unorthodox approach — as well as Uber’s money.

The group, the Independent Drivers Guild, was formed roughly one year ago as part of an agreement for the New York City area between Uber and a regional branch of the International Association of Machinists and Aerospace Workers. Guild officials say the unusual deal was simply the most practical way to improve the lot of drivers, whom the union has a proud history of organizing.

“The drivers need help, and they need help now,” said James Conigliaro Jr., the founder of the guild and a senior Machinists official.

And the guild, which says it represents about 50,000 ride-hail drivers in the New York City area, has produced concrete victories. It took the lead in persuading the city’s Taxi and Limousine Commission to propose a rule that would require a tipping option on Uber’s passenger app, potentially increasing drivers’ income by hundreds of million of dollars.