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Cindy Grossman began their career in 1992 as a Counselor at Family Service Association. Cindy then became a Student Advocate at O'Farrell Community School. In 1995, they began working at Home Start, Inc. as a Safe Futures Counselor. Cindy was promoted to Program Manager in 1997 and Program Director in 1999. In 2004, they left Home Start to become the Program Director/Supervisor of SANDAPP at the San Diego Adolscent Pregnancy and Parenting Program/San Diego Unified School District. Cindy remained in this position until 2012 when they became the Executive Director at Kids' Turn San Diego.

Cindy Grossman has a Master's degree in Social Work from San Diego State University-California State University and a Bachelor's degree in Individual and Family Studies from Penn State University.