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Jenn Cullen has a diverse work experience spanning different industries. Jenn is currently working as an Executive Assistant at HemWell MD and Medfiniti N.V., starting in 2021. Prior to this, Jenn held the role of Chief Administrative Officer at Mirku, a software company, from March 2016 onwards. From October 2018 to 2020, they worked as a Mortgage Banker at Atlantic Bay Mortgage Group. Before that, Jenn was a Manager at CreditRepairProgram.com from November 2015 to January 2018. Jenn also has experience as a High School English Teacher at Pinellas County Schools from July 2011 to November 2013. Jenn started their professional career as a Product Marketing Manager at Barnes & Noble, Inc. from August 2007 to May 2011.

Jenn Cullen completed their education at the University of South Florida, where they received a Bachelor's degree in Mass Communication/Media Studies from 2007 to 2011. In addition to their degree, they have obtained several certifications. Jenn obtained a Mortgage Loan Originator license from NMLS in August 2018, a Credit Repair Specialist certification from Advanced Credit Academy in January 2018, and is also certified as an Agile Marketing Specialist (CAMS) from Agile Marketing. The specific month and year of their CAMS certification are not provided.