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Gunnar Olson has been working in college advising and counseling for over 20 years. Gunnar started their career as an admissions officer at Adelphi University and then Kalamazoo College. Gunnar then became an assistant director of college counseling at Saint Mary's Hall. After 13 years at Indian Springs School, they became the director of college advising at Kimball Union Academy, where they have been for the past 3 years. Gunnar is also a member of the board of trustees for the Association of College Counselors in Independent Schools (ACCIS).

Gunnar Olson has a B.A. from Gettysburg College in German, an M.L.I.S. from The University of Alabama in Information Studies, and a Diploma from Hebron Academy. Gunnar has also completed Dale Carnegie Training at the Diplomat, Leader, and Organized Professional levels. Additionally, they have a certificate in copyediting from the University of California San Diego.

The colleagues that work closest with Gunnar Olson are the other directors and the Dean of Students. They all work together to make sure the students are getting the best education and experience possible.