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Rob Bailey has a diverse work experience spanning several companies.

Starting in 2009, they worked at EMC as both an Enterprise Account Manager from August 2011 to July 2016 and as a Business Development Account Manager from May 2009 to August 2011.

In 2016, Bailey joined SHI International Corp. as an Enterprise District Sales Manager and held this role until February 2022.

Most recently, in February 2022, they joined Samsara as a Region Sales Director. Samsara is an Industrial IoT company that helps organizations improve their operations and safety.

Rob Bailey attended Bentley University from 2004 to 2008. During their time there, they studied Business/Commerce, General. However, no specific degree was mentioned.