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Richard Maitland has worked in the customer success field for over a decade. Richard began their career in 2010 as an Assistant Manager at Brio Bar Corp. In 2016, they moved to Boomset as a Director of Recurring Revenue, Senior Customer Success Manager, and Account Manager. In 2021, they joined Hopin as a Customer Success Engineer, Senior Customer Success Manager, and Renewals Manager. Currently, they are a Customer Success Manager at Anecdotes.

Richard Maitland's education history includes a High School diploma from Titchfield High School, obtained between 1996 and 2002 with a focus on Business/Commerce, General. In 2003 and 2004, they obtained a Diploma from the University College of the Caribbean, with a focus on Marketing. In 2012, they attended Fordham University, obtaining a Bachelor of Arts in Economics, although they did not complete the degree. That same year, they also attended the Investment Banking Institute, obtaining Professional Training in Investment Banking, Corporate Finance & Valuation Analysis. In February 2022, they obtained a certification in Customer Success for Growth from the Winning by Design Revenue Academy.