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Jason Woolard has a diverse work experience in various roles and positions. Jason started as a Civil Engineer Officer in the United States Air Force from 2000 to 2006. Jason then joined JE Dunn Construction as a Project Manager from 2007 to 2009. In 2010, they worked as a Military Master Planner at HDR until 2011. Since then, Jason has been employed at PINNACLE CONSULTING GROUP. Jason started as the Director of Capital Infrastructure Project Management and eventually held positions such as Director of Management and Administration, Vice President Operations, and currently serves as the Chief Operating Officer.

Jason Woolard received their Bachelor of Science degree in Civil Engineering from Colorado State University from 1995 to 2000.