Ramzi Raguii, a driver for the car-hire service Uber, was on vacation in Tunisia when he got word that the company had hired some political muckety-muck named David—David Plouffe, who ran Barack Obama’s 2008 Presidential campaign and later served in the White House—as its senior vice-president of policy and strategy.

Uber is an app that lets you hail a car: tap the screen and a car, with a driver, shows up wherever you are. Drivers sign on as independent contractors and use their own vehicles; Uber takes a twenty-per-cent commission on each fare. Raguii, who is thirty-two years old, told me that he became an Uber driver, in San Francisco, in October of 2013. “A lot of my homeboys are based in San Francisco,” he said over the phone. “They introduced me to Uber. They said, ‘Ramzi, you can do this for a little while.’ My other option was to have a full-time job and only have the option to have a fifteen-day vacation. And so I did Uber.”

The service is popular among riders: an internal document leaked to the blog Valleywag late last year suggested that, each week, people worldwide were taking about eight hundred thousand Uber rides. Drivers, meanwhile, appreciate the flexibility, autonomy, and ease of joining. The appeal of Uber is similar to that of Airbnb, which lets people rent out their homes to vacationers for a night or longer, or Taskrabbit, which matches people who need odd jobs done with those willing to do them for a fee. Before the Internet, the reasoning goes, those who needed services and those who could provide them had fewer ways to find one another; companies like Uber use our newfound connectedness to put us in touch. What’s more, the companies can profit handsomely because they don’t actually own the property used to provide the service—the cars, in Uber’s case, or apartments, for Airbnb.

Investors recently valued Uber at nearly twenty billion dollars, which struck some people as an absurdly high figure. But others, including Andrew Ross Sorkin, have written that Uber could, in fact, be worth more than that—not only because transportation is a big business, but because the company has the potential to do much more with its matchmaker app. Since Uber doesn’t own a fleet of cars or employ its drivers, it could, in theory, deploy its app for any number of other purposes. First it could displace the taxi industry. Then it could take on delivery trucks, moving vans, and more. Earlier this week, the company started testing out a home-delivery service in Washington, D.C.

Raguii admires Uber for being innovative, but he has become an outspoken critic of some of its policies. He said that he is particularly frustrated by the fact that Uber keeps lowering fares, which lets it undercut competitors but also limits drivers’ earnings. He also wishes that Uber would increase the level at which it insures its drivers. (Unsurprisingly, this recalls some of the complaints of unfairness from those who do business with another, more established company with impressive technology: Amazon.) To mobilize other disgruntled drivers, Raguii recently started an organization called the Drivers Network. It’s the best solution he can come up with, he said, because, in his opinion, politicians and regulators haven’t offered much help.

This isn’t for lack of pressure. Individual drivers like Raguii might not have much political influence, but lobbying groups representing traditional industries have worked hard to persuade the government to regulate their newer rivals more closely. In San Francisco, for instance, taxi operators have to provide a million dollars of liability coverage for their cars at all times; Uber, until recently, covered vehicles only when they held a passenger. But Uber, and companies like it, argue that they’re completely different from the industries that they’re displacing—taxis, hotels, employment agencies, and so on—and shouldn’t have to follow the old, fusty regulations that apply to those industries. Yellow cabs, unlike Uber cars, don’t double as personal vehicles.

In these companies' early days, no one seemed to complain much about that reasoning. But, in the past year, that has started to change. In the fall, Eric T. Schneiderman, New York’s attorney general, subpoenaed Airbnb for information about its hosts—some of whom seemed to be operating in defiance of a law that barred short-term rentals in most cases. In April of this year, Schneiderman followed up with a stern Op-Ed in the Times about startups like Uber and Airbnb. “Amazingly, many of these companies claim that the fact that their goods and services are provided online somehow makes them immune from regulation,” he wrote. “This isn’t smart, or sustainable. Just because a company has an app instead of a storefront doesn’t mean consumer protection laws don’t apply.” He went on to announce that his office was investigating whether Uber’s surge pricing, in which it charges more during periods of high demand, violated New York’s price-gouging laws. Schneiderman has had some victories since then: in May, Airbnb agreed to hand over some of the information that his office sought; in July, he announced that Uber had agreed to cap its prices during emergencies, in keeping with the law.

Now, in California, a Democratic state legislator named Susan Bonilla is pushing a bill that would tighten auto-insurance regulations for transportation companies like Uber. (Bonilla proposed the legislation—which is supported by insurance companies—after an Uber driver hit and killed a six-year-old girl in San Francisco. The driver’s Uber app was turned on, but he wasn’t carrying a passenger, so Uber said that he, and not the company, should be held responsible.)

Plouffe, in his new role, will be in charge of “all global policy and political activities, communications, and Uber branding efforts,” Uber’s C.E.O., Travis Kalanick, wrote in a blog post. This is a broad purview—Plouffe has said, in interviews, that he expects to “campaign” for Uber just as he did for the President—but, presumably, part of the job will be figuring out how to address challenges like the ones in California and New York. It will also include lobbying the government to come up with policies that are more favorable to Uber’s interests in the first place.

Raguii hadn't heard of Plouffe, but he said that he feels like he knows the type. “You’ve got tech-savvies running a cab company, and now they’ve got this David guy,” he said. “My opinion?” He said that he believes Uber has stayed under the radar of the regulatory establishment for the past several years. Now that there are signs that this is changing, the company needs someone who can give it good advice. “I mean, this guy’s job is obvious—to tell these guys, how are we going to dodge the rules? How do we cut corners?”

One of the few interviews that Plouffe and Kalanick gave on Tuesday was with Politico, to which they described their mission differently. “We’ll be trying to change the point of view of established politicians, and there’s a lot of resistance coming from people who want to protect the status quo,” Plouffe said.