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Jessie W. has extensive work experience in the healthcare industry, particularly in organizations related to reproductive health and family planning. Starting in 2012, Jessie worked as a Medical Assistant for Planned Parenthood of Orange and San Bernardino Counties. In 2015, Jessie joined Adolescent Growth as a Medical Assistant and later took on the role of Assistant Program Manager. Jessie then moved on to work at Planned Parenthood Los Angeles in 2017, where they served as a Medical Assistant and later as a Medical Assistant 3. In 2022, Jessie joined Planned Parenthood Great Plains as a Reproductive Health Assistant and also worked as a Public Affairs Administrative Assistant and Organizing & Campaign Specialist for Planned Parenthood Pasadena and San Gabriel Valley. Jessie's roles have showcased a commitment to healthcare and reproductive rights advocacy.

Jessie W. attended Mt. San Antonio College from 2021 to 2025, focusing on the field of study in Social Justice. There is no mention of obtaining a degree during this time. Alongside their college education, Jessie W. obtained additional certifications as a Certified Phlebotomy Technician (CPT) from the AUMT Institute and as an NHA-Certified Phlebotomy Technician (NHA-CPT) from NHA, although specific details on when these certifications were obtained are not provided.