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Rachel Simkiss has a diverse work experience in the art and charity sectors. Rachel started their career at Halcyon Gallery as a Marketing Manager from an unspecified date until 2007. In 2007, they founded the Silver Pearl Trust, where they served as a Trustee until 2016. During their time at the trust, they organized various charity events and built relationships with corporate brands for funding and sponsorship. Since 2010, Rachel has been associated with Clarendon Fine Art, where they held multiple roles. Rachel started as the Marketing & Communications Director from May 2010 to July 2012, then became the Gallery Director from July 2012 until September 2020. Currently, they hold the position of Director of Brand for Clarendon Fine Art Galleries since September 2020.

Rachel Simkiss attended Portland House School and Leicester High School from 1987 to 1993. Rachel then pursued an Art Foundation degree at DeMontfort University from 1995 to 1996. Afterward, they enrolled at Solent University, where they completed a BA(Hons) in Art History & Fashion Design from 1997 to 2000.