December 15, 2023

Dear Riley Facilitators, Families and Friends:

I am thrilled to announce that Riley’s Board of Trustees has unanimously selected Annie Hasselgren as our next Head of School. Annie will formally begin July 1, 2024. On behalf of the Board and the entire Riley community, I want to thank Chair Chrisso Rheault, co-Chair Christine Chamberlain, Bill Kinnane, and Mel MacKay, who joined with me on the Search Committee, supported by consultant Chris Williamson, to develop, research and interview an exciting group of candidates. Particular thanks to Bill for his dedication in hosting our finalists and to all in the community who welcomed them. They were very impressed with Riley facilitators, children, parents, board members, and the campus. As you discovered when they came to campus, Riley attracted significant interest from highly qualified candidates. Special thanks to Becky for touring the spouses, meeting with the candidates, and providing her input.

Annie rose to the top for several reasons. She has extensive experience in leadership roles for ten years in independent schools, spanning the ages from toddler to high school. With much of that experience in admissions, she knows how to present a school’s unique strengths and looks forward to articulating why Riley’s program is so impactful for children. She values the authentic progressive education Riley exemplifies. Her role has also included supporting the development effort. At the same time, Annie has deep experience in public relations and had the courage and tenacity to start her own business prior to gravitating to education.  

As important as that background is, equally compelling are Annie’s personal qualities. People warm to her, immediately recognizing her genuine interest and empathy. She enjoys problem solving, is a superb communicator, listens carefully, and is collaborative. She is used to working hard, wearing many hats, creating initiatives and expanding programs such as her school’s summer offerings, and has high standards. She has shown throughout her career that she understands the importance of being highly visible both in her school and in the community, and she does so with integrity.

Annie and her husband Gavin have two children, Finn (current eighth grader) and Ian (currently fifth). They expect to have Ian enroll at Riley. Annie and Gavin will begin their transition to Riley by attending some specific events this spring and meeting with Becky and Facilitators, with families invited to receptions once her visits are scheduled.

We look forward to celebrating Becky’s essential contributions to Riley during the coming months. Riley owes her a tremendous debt for her selfless service to the school for over 35 years and for maintaining founder Glenna Plaisted’s vision. Annie looks forward to continuing that legacy, and we are excited to work with her.

Best wishes for the holidays!

Whitney Oppersdorff, Board President