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Jen Weingarten has had a varied work experience. Jen began their career in 2015 as a Real Estate Analyst for CrediFi. In 2018, they took on two roles, as a Data Analyst for Tzur Management and as a Personal Assistant to the CEO for Rapaport. In 2021, they became an IRG Operations Administrative Assistant for The International Renewals Group. Her most recent role is as a QA Manual Tester for Hometalk, which they began in 2022.

Jen Weingarten obtained a Bachelor of Arts (B.A.) degree in Political Science and Government from the University of Prince Edward Island between 2005 and 2008.