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Sidney Calvin has a diverse work experience. They started their career as a Research Intern at Wellness Coalition in 2009. From 2010 to 2012, Sidney interned at Metropolitan Community Charities LGBTIQ Homeless Youth Services and the Sexual Assault Prevention and Awareness Center, gaining experience in youth services and social work. In 2011, they worked as a Program Development Assistant at the Program on Intergroup Relations. In 2014, Sidney held roles as a Membership Coordinator at the National Association of Social Workers, California Chapter and as a Lead Account Manager at Summit Solutions Inc. They then worked as an Account Executive and Sales Operations Manager at Customer Lobby in 2014, before joining the Contra Costa County Homeless Programs as the HMIS Administrator in 2016. They also served as a Project Manager and later as the Director of Technology at Performance Based Ergonomics from 2016 to 2021. Since 2021, Sidney has been working at EverCommerce, initially as an Operations Strategist and currently as the Head of Business Operations.

Sidney Calvin received a Bachelor of Arts degree in Psychology and Anthropology from Hampshire College in 2011. Between 2011 and 2013, Sidney pursued a Masters of Social Work degree at the University of Michigan, focusing on Community Organization and Interpersonal Practice.