Ashwini Chhabra, deputy commissioner of policy and planning at the New York City Taxi and Limousine Commission, will be joining Uber as the startup's first head of policy development and community engagement.

The Commission has had an at-times adversarial relationship with Uber, which launched its yellow cab-hailing app in New York City without approval and had to pull it back. Since then, the commission has affirmed its belief that hailing apps are good for New Yorkers, but forced Uber to go through a bureaucratic process that gave its competitors time to catch up. Having lost its first-mover advantage, Uber is now up against similar apps including Hailo and Taxi Magic.

Chhabra was one of the more open-minded commission officials during the battle to introduce hailing apps into a city with a firmly-established taxi industry. He hardly carried water for Uber, however, noting that hailing apps could disadvantage riders without smartphones and should be banned "in places where they will be particularly disruptive," like at taxi stands.

Uber has hired government insiders before, taking on former Bloomberg aides Bradley Tusk and Stu Loeser as lobbyists in New York and former Rahm Emmanuel fixer Michael Kasper in Chicago. It's a smart strategy considering all the legal hurdles the company has faced in its efforts to upend the taxi industry. The company operates in more than 100 cities worldwide, and may now be gearing up for its next battle: Las Vegas, where it will have to convince not just one, but two regulatory agencies that are skeptical of the new technology. Perhaps Chhabra can reason with them.