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Jessica Reif has worked in various roles in the fields of research and data analytics since 2008. Her earliest role was as a Sales Associate and Youth Golf Coach at Eagle Golf in 2008. Jessica then worked as a Human Resources Assistant and Summer College Residential Community Advisor at the Samuel Curtis Johnson Graduate School of Management in 2011. In the same year, they also worked as a Research Assistant at the Johnson Graduate School of Management at Cornell. In 2012, they were a Summer Data Analyst at McLagan, An Aon Hewitt Consulting Company. In 2013, they were a Global Human Resources Solutions Intern at PwC.

In 2014, Reif began their work at CrossLead, first as a Research and Data Analyst at the McChrystal Group, then as a Manager, Analytics - Team Lead, Research and Analytics Advisor, and finally as Director, Research & Development | Client Services. In 2017, they moved to Oracle as a Product Delivery Manager, Applied Machine Learning & Data Science Products.

Jessica Reif has a Bachelor of Science in Industrial and Labor Relations from Cornell University. Jessica is currently pursuing a Doctor of Philosophy in Management & Organizations at Duke University - The Fuqua School of Business, which they are expected to complete in 2026. Jessica also has certifications from Scaled Agile, Inc. (SAFe Product Owner / Product Manager and SAFe 4 Agilist), CrossLead (CrossLead Team Leader), Scrum.org (Professional Scrum Master (PSM-I)), and Scaled Agile, Inc. (SAFe Scrum Master (SSM)).