His most prominent roles were as CEO of several large companies in the transportation industry: Northwest Airlines (2001–2004), Delta Air Lines (2007–2016), and Amtrak (2017–2020).

[1] Anderson, who had never considered a career in the aviation industry, accepted the position at the urging of Ben Hirst, a neighbor who worked at Continental as a legal counsel.

[5][6] In 2010, during his tenure at Delta, Anderson led an anti-union campaign against the Association of Flight Attendants, calling the labor union "un-Christian" and "immoral.

[9] In June 2017, Amtrak announced Anderson as the organization's next President and CEO, replacing Charles "Wick" Moorman.

Anderson remained co-CEO with Moorman until the end of 2017, at which time he assumed the role of sole CEO.

On March 2, 2020, it was announced that Anderson would step down as CEO on April 15, 2020, after fulfilling his three-year commitment to the company.