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Lindsay O'Sullivan

College Counselor


Meet Lindsay O'Sullivan

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Throughout her impressive career, Lindsay has exemplified that making connections is what makes it all rewarding. She has consistently valued building meaningful, interpersonal connections with students and their families across many academic communities. In her positions as an admission officer for both Pomona and Occidental Colleges; in her directorship in admissions at Marymount High School in Los Angeles; and as assistant director of college counseling for Woodberry Forest School in Virginia, she has shown she cares deeply about her students and works tirelessly to help them find their way forward into college and life.

Lindsay also has mad editorial skills under her belt: she worked as an assistant editor for Rice University’s Office of Public Affairs and as chief editor of publications for the Chicago International Film Festival (cinephiles, get your film trivia ready—Lindsay also received her M.A. in the Humanities from University of Chicago with a concentration in Cinema and Media Studies).

Prior to joining Collegewise, she worked as a seasonal application reader for Occidental, because (you guessed it) she enjoys staying connected, especially to ever-changing admissions trends. While her career has taken her to London, Chicago, Houston, Virginia, and California, Lindsay currently resides with her family outside of Cleveland, OH.

Education & Experience

  • Former Assistant Dean of Admission, Occidental College and Pomona College
  • Former Admissions Communications and LL.M. Program Coordinator, University of Chicago Law School
  • Former Assistant Director of College Counseling, Woodberry Forest School, and Former Director of Admission, Marymount High School

Contact Lindsay O'Sullivan

What are people saying about Collegewise?

We simply could not have navigated the college application process as well as we did without Collegewise. I believe that without Collegewise, we never would have found such a great fit for our daughter and the process would have been much harder.

JR Hughson, Parent of Samantha Hughson

Clark University

Sophie looked forward to her appointments and did the prep work religiously. Collegewise took the right approach, with clear guidance but a light touch in terms of letting Sophie drive the decision-making. Sophie owned her approach and ended up happy with her options.

David Lindheimer, Parent of Sophie Lindheimer

The University of British Columbia

When I first started this process of looking for colleges, I didn’t know where to start or what I wanted my end goal to be. Collegewise helped me to tackle every task step by step. They helped me to understand exactly what I was looking for in a college. They helped me achieve my goal, and I couldn’t be more grateful.

Lisa Costantino

Syracuse University

I am so happy that we made the decision to have Collegewise help our daughter prepare her college applications. With the help from Collegewise, my daughter got into some great colleges this year. She got help from her counselor with every aspect at any time she needed it. It was absolutely worth the money I spent for my daughter.

Jenny, Parent of Belinda

Scripps College

My one fear was that college counseling would make my son less involved in the process, but it did the opposite! Our counselor was cool, calm, and collected and treated him as a young adult and unique individual. That really helped him look forward to the meetings and rise to the occasion of college applications with success.

Elizabeth James, Parent of Alexander James


Collegewise helped me so much from the start to finish of my college application period and made everything so much more fun and easy to understand than if I went through the process all by myself. I cannot recommend Collegewise enough.

Raaya Alim

UMass Amherst