Uber Technologies Inc Chief Financial Officer (CFO) Nelson Chai has planned to resign. This marks the most significant executive departure since the company’s IPO 2019.

Chai informed Chief Executive Officer Dara Khosrowshahi of his intentions to step down, though a decision regarding the timing is yet to be made.

Chai oversaw some of Uber’s biggest highs and lows as a public company. San Francisco-based Uber made several multibillion-dollar deals, including the $2.65 billion acquisition of Postmates in 2020, logistics operator Transplace for $2.25 billion in 2021, and purchases that played a crucial role in helping Uber diversify beyond rides. When the pandemic obstructed the demand for ride-hailing, Uber’s bookings were cut down to as much as 80%, and the company laid off more than 6,000 employees.

In 2022, Chai helped Uber to its first-ever quarter of positive EBITDA of $186 million. The company did strip out some expenses, which served as a solid indication to its stakeholders that Uber is moving past its growth-at-all-costs phase.

Before Uber, Chai had been a longtime lieutenant of Wall Street veteran John Thain, the former top-ranking executive at Goldman Sachs Group Inc. He later went on to take a senior role at the New York Stock Exchange with Merrill Lynch and CIT Group, crossing paths again with John Thain.