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Dena Boutwell has held a variety of positions over the past 20 years. In 2000, they were the Director of Sheriff's Youth Programs of Minnesota. Two years later, they became a Secondary Education Social Studies Teacher at New Ulm Public School. In 2005, they were a Regulatory Specialist at Alta Colleges, LLC. From 2006 to 2008, they were the Training and Recruiting Coordinator at Specialty Sports Venture (Vail Resorts). During this time, they trained management staff throughout CO, CA & NV and recruited and interviewed candidates at all levels for the company. From 2008 to 2015, they were the Compliance Manager & Special Needs Supervisor at Boulder Valley School District, where they supervised special needs school bus drivers and student assistants, managed special needs routes, and managed all department training and compliance. In 2015, they became a Board Member at The Acorn School for Early Childhood Development. From 2018 to 2019, they were the Safety Director at Via Mobility Services. Currently, they are the Advisory Council Chair at Boulder County Area Agency on Aging.

Dena Boutwell attended Minnesota State University, Mankato from 1997 to 2002. Dena also holds certifications as a CPI Nonviolent Crisis Intervention Trainer from the Crisis Prevention Institute and as a Ken Blanchard Situational Leadership II Trainer from The Ken Blanchard Companies.