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Jessica Kobos has a diverse work experience, starting in 2013 as an Operations Analyst at VISION Relocation Group, where they served as a communication liaison and handled data processing. In 2014, they joined USIS as an Associate Investigator, conducting background investigations. Later in 2014, they moved to CACI International Inc, initially as a Background Investigator and then as a Market Research Analyst. Jessica joined Long & Foster Companies in 2016 as the Director of Operations & System Platforms for Long & Foster Property Services. In 2018, they transitioned to HomeServices Property Management, continuing as the Director of Operations & System Platforms.

Jessica Kobos completed their education with a Bachelor of Arts (B.A.) degree in Criminology/Pre-Law from Indiana University of Pennsylvania between 2009 and 2013. Prior to that, they obtained their High School Diploma from Chantilly High School between 2005 and 2009. In addition to their formal education, they also obtained certifications as an Insurance Agent, specializing in Property & Casualty, from the National Insurance Producer Registry. Jessica obtained the certification for Maryland at an unspecified time and for Virginia in July 2017.