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Sierra Webster-Calvert has a diverse work experience that spans various industries and roles. Sierra started their career in 1998 as an Office Manager at ITG Pathfinders and worked there until 2001. From 2001 to 2011, Sierra served as the Operations Manager at Premier Accessories. In 2006, they became a Real Estate Agent at Prudential PenFed Realty and held that position until 2012. Sierra then worked as an HR Coordinator at Westside Family Healthcare from 2013 to 2013, where they provided administrative support to the HR department. Next, they became an Office Manager at Del Val Structures, Inc. from 2013 to 2014. Sierra then transitioned to the role of Financial Operations Manager at Westside Family Healthcare from 2014 to 2019, before becoming the Director of Revenue Cycle in 2019. Additionally, they worked as a Salesperson at RE/MAX Vision from 2013 to 2017 and is currently employed as a Licensed Realtor at Patterson-Schwartz Real Estate since 2018.

Sierra Webster-Calvert holds an Associate of Arts (A.A.) degree in Business Administration and Management, General from Delaware Technical and Community College-Stanton-Wilmington. No specific dates were provided for their education at this institution.