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Robert Littlefield has a diverse work experience in various managerial roles. Robert started as a General Manager at Pratt & Whitney in 2001 and worked there until 2010, managing multiple engine centers and achieving operational objectives. In 2010, they joined Precision Castparts as a General Manager before becoming the President of the Chicago Magnesium Casting Company in 2013. Robert also worked as a Just-In-Time Consultant in the same year. Additionally, they had a consulting role in the Kaizen Promotion Office at Pratt & Whitney from 1990 to 1992.

Robert Littlefield completed their education in two institutions. From 1984 to 1995, they attended Eastern Connecticut State University, where they earned a Bachelor of Business Administration (B.B.A.) degree in Business Administration and Management, with a focus on general studies. Following this, from 2006 to 2014, they pursued a Master of Science (M.S.) degree in Accounting at Rensselaer at Work.