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Ian Weiland has a diverse work experience in the transportation and logistics industry. Ian started their career in 2014 at Junction Collaborative Transports, where they held the role of Director of Enterprise Sales for four years. In 2018, they became the Chief Operating Officer at Junction Collaborative Transports. In the same year, they also joined Junction Cargo Brokers as their Chief Operating Officer. Additionally, they worked at Landstar as part of their Logistics Supply Chain team from 2014 to 2017.

Ian Weiland attended the University of Maryland from 1999 to 2003, where they earned a Bachelor of Arts (BA) degree in Economics.