Uber Technologies Inc. this morning bolstered its leadership team with the appointment of Barney Harford (pictured), a former executive at travel aggregator Expedia Inc., as chief operating officer.

Harford’s career has followed an interesting trajectory. He joined Expedia in 2004 as the president of its Asia Pacific business shortly before Dara Khosrowshahi, Uber’s chief executive officer, came aboard as well to head the company. The two then worked together until Harford took the CEO role at rival Orbitz Worldwide Inc. in 2009. In the final twist, Expedia acquired Orbitz for $1.6 billion a few years later.

Harford has reportedly been working as an adviser to his former boss-turned-competitor-turned-boss-again at Uber since October. In the hiring announcement, Khosrowshahi said the executive was busy learning how the company operates and “developing perspectives on how it can work even better in the future.”

Once he formally takes over as COO on Jan. 2, Harford will be tasked with overseeing all of Uber’s core business activities. That includes first and foremost global ride-hailing operations. He will also provide direction for the marketing and customer support groups, as well as the company’s food delivery division.

The appointment of Harford as COO comes at a crucial time for Uber. The ride-hailing giant reportedly lost a hefty $1.46 billion in the third quarter, up from $1.06 billion three months earlier, on net revenue of $2 billion. A fresh perspective may be just what the company needs to start climbing out of the red, but Harford will have his work cut out for him.

Uber has suffered a string of controversies and regulatory setbacks over the past year. The most recent blow came just this morning when the Court of Justice of the European Union ruled that it should be classified as a transportation company. This decision will enable the bloc’s member states to place stronger legal restrictions on Uber, which would incur new compliance costs in a time when its losses are already growing rapidly.

Khosrowshahi, Hartford and the rest of the leadership team will likely have a challenging 2018.

Image: Uber