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Hailee Jacobson has a diverse work experience in the healthcare and retail industries. Hailee started their career at Premier Plastic Surgery Group in 2000, where they served as an Administrator. In this role, they were responsible for guiding cosmetic patients through the surgery process, scheduling procedures, and managing call schedules for multiple physicians until their departure in 2009.

Following their time at Premier Plastic Surgery Group, Hailee joined Dermatology Partners Inc as a Retail Director I Product Educator. Their primary responsibility in this role was to guide patients in selecting suitable skincare options based on their desires, budget, and time commitments. Hailee's expertise in skincare constantly evolved during their tenure, which lasted from 2009 to 2019.

In 2015, Hailee transitioned to RegimenMD, where they served as the Director of Physician Training and Acquisition. Hailee held this position until joining California Closets in 2019 as a Design Consultant, a role for which no end date was provided.

Hailee Jacobson attended Westminster College from 2007 to 2009, where they studied Registered Nursing/Registered Nurse. It is unclear whether they completed a degree or pursued further studies in this field.