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Hale Bartholomew has extensive work experience in various technical roles. They started their career in 1997 as an Applications Specialist at xpedx, where they configured and installed digital prepress solutions and provided training and technical support to end users. They then worked at Creo from 1998 to 2004, where they held multiple roles including Technical Sales Support, Applications Support Specialist, and Field Product Specialist. At Creo, they evaluated client systems, provided technical solutions, and supported software and hardware implementations. Hale then worked as a Tier 2 Engineer at 24x7 I.T. Solutions from 2010 to 2011, and as a Client Technical Analyst at the Port of Portland starting in 2011. Most recently, they have been working for Rambling Shoes since 2019, where their role involves traveling the world.

Hale Bartholomew attended the State University of New York at Oswego from 1990 to 1995, where they obtained a Bachelor of Science degree. During their time at the university, Hale studied Accounting and Art.