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Jessica LeMay has a diverse work experience in various industries. Jessica began their career in 1999 at Asante as a Certified Pharmacy Technician, where they assisted healthcare providers and patients by answering inquiries, processing prior authorizations, and following up with patients' results. In 2018, they joined Hunter Communications as a Telecommunications Billing Specialist/Voice Provisioner/Project Coordinator/Procurement Specialist, responsible for overseeing and performing telecom billing functions. Jessica also became the Director of Customer Experience at Hunter Communications in February 2022. In the same year, they also worked as an Independent Consultant for Pampered Chef.

Jessica LeMay attended Rogue Community College from 1999 to 2002, focusing on Chemistry. Jessica did not obtain a degree during this time. Additionally, they obtained a certification in Leadership Principles from Harvard Business School Executive Education in December 2021.