Uber’s plans to recruit a new chief financial officer come as the ride-hailing company’s financial team grapples with a host of challenges ahead of a possible IPO.

Those tests include helping figure out a path to turn a multibillion-dollar loss last year into a profit, lowering per-trip costs, and dealing with standard regulatory requirements and potential tax issues. Interviews with people involved with Uber’s finance team provide a window into how Uber views its competitive advantages and difficulties, and how some early assumptions about the ride-hailing market have been dashed.