Just a few months ago, things were going well for Alibaba CEO and chairman Daniel Zhang. Despite the global pandemic, China’s economy was bouncing back and strong e-commerce demand was boosting Alibaba’s revenue and share price. Time magazine in September named Zhang one of the world’s 100 most influential people, along with U.S. President-elect Joe Biden and Vice President–elect Kamala Harris. In late October, Alibaba’s market capitalization soared to a record high of more than $860 billion, making it more valuable than Facebook at the time.

But now, Zhang’s leadership is being tested like never before. The Chinese government has targeted Alibaba in its recent antitrust scrutiny, while Alibaba’s financial technology arm, Ant Group, is grappling with new online lending regulations that threaten to hobble its business. Zhang, an unassuming former accountant and longtime Alibaba executive who succeeded iconic founder Jack Ma as chairman in 2019, has earned a reputation as a seasoned operations expert with good long-term business ideas. But he has less experience dealing with governments. And some investors and bankers say they aren’t sure how well Zhang can handle the political hurdles.