He graduated from Cornell University with a Bachelor of Science in Applied Economics in 1983. He then went to work for Procter & Gamble, then he became Senior Director of National Marketing at Pizza Hut. He has also been head of marketing for Guinness and Chief Marketing Officer at Derby Cycle Corporation. He was then senior vice president at Panda Management Co., taking the same position at VH1 later, boosting their ratings by 30%.
He joined Nintendo in December, 2003, as the Executive Vice President of Sales and Marketing, overseeing Canada, North America, and Latin America.
He became the President and Chief Operating Officer of Nintendo of America on May 25, 2006, after former president, Tatsumi Kimishima, was promoted to Chairman of the Board and Chief Executive Officer. Reggie gained popularity with his opening statement at Nintendo's E3 press conference, "My name is Reggie. I'm about kickin' ass, I'm about takin' names, and we're about makin' games." After Satoru Iwata's passing, Reggie became the new public figure of Nintendo as a whole since Kimishima (who became the 5th president of Nintendo) was not as willing as Iwata into taking part in the direct communication of the company. Since then he has been seen hosting the E3 conferences and making transitions in the Nintendo Directs like Iwata used to.
On February 21, 2019, it was announced that Reggie would be retiring from the company, with his last day being April 15, 2019. Doug Bowser succeeded Reggie in the role of President and COO of Nintendo of America.
- Prior to the 2007 Nintendo conference at E3, Shigeru Miyamoto on three different accounts asked Reggie if he could perform the Hula Hoop minigame from Wii Fit on stage. On all three accounts Reggie declined, including the day of the event, in which he claimed that his back was hurting. Miyamoto later stated that employees back in Kyoto told Miyamoto that he should never have asked the president to perform such a task on stage.