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Jason DeGray started their career in 2002 as a traffic engineer at BETA Group, Inc. Jason then worked as a Senior Project Engineer at VHB from 2007 to 2010. After that, they joined The Beta Group, Inc. as a Senior Project Engineer from 2010 to 2012. Subsequently, they worked as a Project Manager at GPI / Greenman-Pedersen, Inc. from 2012 to 2016. Currently, they are the Boston Office Director at Toole Design Group since October 2019, previously serving as the New England Regional Engineering Director from 2016 to September 2019.

Jason DeGray earned a Bachelor of Science degree in Mechanical Engineering from Boston University, graduating in the year 2000. Jason then pursued a Master of Science degree in Transportation and Highway Engineering from the University of Massachusetts Amherst, completing their studies in 2002. In 2006, they obtained their Professional Engineer (PE) certification from the Commonwealth of Massachusetts. Additionally, in 2007, they obtained the certification of Professional Traffic Operations Engineer (PTOE) from the Transportation Professional Certification Board.