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Robert Appelbaum has extensive work experience in sales and account management positions. In 2009, they worked as a Camp Counselor/Administrator at Camp Menominee until 2014. From 2015 to 2015, they worked as a Camp Counselor at JCC "Z" Frank Apachi Day Camp. In 2017, they joined RevenueWell as a Sales Development Representative Team Lead until 2019, when they transitioned to the role of Account Executive Team Lead until 2021. In 2021, they joined Service Express as an Account Executive and later became a Senior Account Executive until 2022. From 2022 to 2023, they worked as a Sales Manager at Winsight, LLC. Currently, they are working as a Senior Account Executive at Instawork, starting from July 2023.

Robert Appelbaum earned a Bachelor of Arts (B.A.) degree in Sports' Studies from the University of Iowa between 2011 and 2015. Robert also pursued a minor in American Studies during their time at the University. In March 2021, they obtained the Winning by Design - SaaS Sales Method Certification from Winning by Design.