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Jacob VanDrie started their work experience in 2016 as a Shift Leader at Jimmy John's, where they worked until 2018. In 2019, they worked as a Data Analyst at Huck Bouma, PC for a few months. Later in the same year, they became a Financial Advisor at Northwestern Mutual until September 2020. In 2021, Jacob joined Magid as a Corporate Accounts Support Analyst, and in 2022, they were promoted to the role of Corporate Accounts Analyst. Currently, they work as a Senior Financial Analyst at FCB Chicago.

Jacob VanDrie received their Bachelor of Business Administration - BBA degree in Finance and General Business from Western Michigan University, where they studied from 2017 to 2021. In addition to their degree, they obtained two certifications: Bloomberg Market Concepts from Bloomberg LP in March 2020, and an Insurance Agent certification for Accident, Health, Life, Variable Life, and Variable Annuities from the State of Michigan in January 2020.