Early in her career Wainwright began working for The Clorox Company in brand management and computer software.
[2] By 1996,[3] she had replaced Wes Boyd as CEO of Berkeley Systems[4][5] where she was instrumental in changing the company's strategy by making it a leading interactive entertainment entity.
"[16][17][18] Wainwright was approached by John Hummer of Hummer Winblad Venture Partners to run Pets.com, and was CEO of Pets.com when it ceased operations 268 days after its initial stock offering — "one of the shortest-lived public companies on record" according to Kirk Cheyfitz, author of Thinking Inside the Box: The 12 Timeless Rules for Managing a Successful Business.
Wainwright is an advisor to Springboard Enterprises’ New York Fashion Tech Lab and Purdue University's Krannert School of Management.
[39] Wainwright was selected for the inaugural 2021 Forbes 50 Over 50; made up of entrepreneurs, leaders, scientists and creators who are over the age of 50.