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Jacob Gilland has a diverse work experience starting from 2019. Jacob worked as a Statistician at Genius Sports from August 2019 to April 2022. From October 2021 to April 2022, they were the Director of Player Development at Recruitment Hockey. Jacob also worked at Grand Rapids Marketing Group, where they served as a Marketing Specialist from September 2020 to January 2021 and as a Corporate Trainer from January 2021 to March 2021. In September 2021, Jacob joined Reeths Puffer Hockey as a Hockey Coach. From September 2022 to July 2023, they worked as a Sales Development Representative at ZoomInfo. Jacob is currently working at CRI Advantage as a Sales Development Representative, starting from July 2023.

Jacob Gilland attended Muskegon Community College from 2019 to 2021, where they earned an Associate's degree in Business Administration and Management, with a focus on General Studies. In 2020 to 2021, they also pursued a degree in Hockey Scout and GM from Sports Management Worldwide. Additionally, in 2021, they obtained a Real Estate License from Real Estate Express, specializing in Real Estate.