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Jacob Dempsey has a diverse work experience in various roles and industries. Jacob started their career at South End Civil Inc. in 2012 as a Lead Estimator / Project Coordinator and worked there until 2017. Jacob then joined Purple, Rock, Scissors as a Digital Project Coordinator and later became a Project Manager. In 2018, Jacob joined Barrel as a Producer and eventually moved up to the position of Senior Producer. In 2021, they transitioned to Red Antler as a Senior Project Manager. Currently, Jacob is serving as the Director of Product Marketing at Bilt Rewards, a position they have held since 2024.

Jacob Dempsey holds a Bachelor of Science degree in Marketing from the University of Central Florida. In addition to their degree, they have obtained certifications such as "Getting Things Done" from VitalSmarts in 2020, "Google Ads Search Certified" from Google in November 2018, and "Certified Scrum Master (CSM)" from Scrum Alliance in 2018.