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You are the CEO of a rapidly growing online auto insurance company. The city of New York has recently tendered a request for proposals (RFP) to auto insurers to cover a fleet of 10,000 autonomous driving taxis subsidized by the federal infrastructure and fiscal stimulus plan. The funding allows the proposed city fleet to operate at prices below those of Uber and Lyft, effectively relegating those companies to suburban transport for the New York metro area. The taxi fleet will be owned by the city, and profits will be re-invested into capital improvements for the city’s deteriorating roads and bridges. Cities across the country appear to be following suit in planning similar initiatives. As CEO you have the authority to bid or no bid the RFP. You are also accountable to the board of directors for your decision. The role-play identifies 5 challenges you face. It explores philosophic and ethical concepts that apply to the public debate over both autonomous and self-driving cars. It also provides 3 role-play exercises related to the scenario.