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In 2008, Gaines joined travel company Helloworld.[8] She served as CFO of the company and became CEO in April 2014.[8] In June 2015, she resigned as Helloworld's CEO.[9]
Gaines joined the board of Fortescue Metals Group in 2013,[10] while still CFO of Helloworld. She was the company's first female non-executive director.[11] Gaines was appointed CEO of Fortescue in November 2017 succeeding Nev Power.[12][10] Before becoming CEO, she served as the Fortescue's chief financial officer (CFO).[1][6]
In December 2021, three years after becoming CEO of Fortescue, Gaines announced her future departure from the CEO role, intending remain with the company as a non-executive director on the board and as Fortescue's global green hydrogen ambassador. A global search is underway for her successor.[13]