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Caleb Quakkelaar has a diverse work experience spanning multiple industries. Caleb currently works at WaterStone Bank, starting as a Universal Banker I in February 2021 and moving up to Assisstant Branch Manager in June 2022. In March 2023, they became the Community President. Before joining WaterStone Bank, Caleb worked as a Teller Supervisor at Associated Bank from January 2019 to February 2021. Prior to that, they were a Service Coordinator at Vacuum, Pump and Compressor INC from June 2018 to October 2018. Caleb also worked as a Receiving Clerk at Marine Travelift, Inc. from December 2015 to May 2018. Caleb gained experience in the food industry as a Food Server at Trattoria Dal Santo from September 2014 to September 2016. Caleb also served as a Team Leader in the US Army Reserves from August 2013 to August 2016. Additionally, they worked as a Product Display Specialist at Crossmark, Inc for a brief period in early 2015 and as a Delivery Driver at The Linen Press, LLC from July 2014 to November 2014.

Caleb Quakkelaar attended Marquette University from 2009 to 2013, where they pursued a Bachelor of Arts (B.A.) degree in American Military History.