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Dr. Holmboe is the Chief Research, Milestone Development, and Evaluation Officer, Milestones Department. He is also Professor Adjunct of Medicine at Yale University, Adjunct Professor at the Uniformed Services University of the Health Sciences, and Adjunct Professor at the Northwestern University Feinberg School of Medicine.

He served as the Associate Program Director, Yale Primary Care Internal Medicine Residency Program, and as the Director of Student Clinical Assessment, Yale School of Medicine. Before joining Yale in 2000, he served as Division Chief of General Internal Medicine at the National Naval Medical Center. He also previously served as a medical student clerkship director and residency training officer at the Portsmouth Naval Medical Center. Dr. Holmboe retired from the US Naval Reserves in 2005.