In 1999, Swan joined the dot-com grocery delivery company Webvan as VP of finance. Webvan launched with a ton of hype, and raised some $400 million in venture capital. Webvan raised another $375 million in an IPO the year of its launch, and hit a market cap of $7.9 billion on its first day of trading.
However, Webvan's costs far outpaced its revenue, and it quickly burned through all of its cash. By April 2001, Webvan CEO George Shaheen resigned, and Swan was named the new chief exec.
Four months later, the company filed for bankruptcy and was forced to let go of its remaining 2,000 employees. The company's assets were sold to Amazon. All told, Webvan was only in operation for three years.
Swan held various executive roles over the next several years, including a stint between 2003 and 2006 as CFO of Electronic Data Systems (EDS), the IT outsourcing firm founded by Ross Perot.
After eBay, Swan joined growth-equity firm General Atlantic, where he advised startups on their financial operations. He also helped lead General Atlantic's $158 million investment in AppDynamics, which sold to Cisco in 2018 for $3.7 billion.
Swan became interim CEO in June 2018, replacing Brian Krzanich, who resigned following the company’s investigation into his past relationship with an employee. Reportedly, Swan told employees at an all-hands meeting that he didn't want the job on a permanent basis.