Caleb Dolan is Vice President of Medium Region School Support at the KIPP Foundation He is from Dixmont, Maine and lives outside Boston with his brilliant wife, Joanna, and lively daughters, Tallulah (14), Mavis (8), and Briseida (18).
From 2011 to 2020, Caleb was Executive Director for KIPP Massachusetts. Caleb led KIPP Massachusetts to…

-grow from a single 5-8 middle school in Lynn serving 360 students to the state’s largest public charter network.
-achieve 30%+increases in college matriculation and projected graduation rates.
-increase diversity of staff from 15% BIPOC to 50% BIPOC with similar representation at all levels of leadership.
-double the number of students reading and doing math at or above grade level.
-support KIPP MA families become the most engaged in the Boston charter sector.
-raise over $30 million to grow an organization that is sustainable on public funding and built three permanent facilities.
From 2009-2011, Caleb served roles as an instructional leader for KIPP Academy Lynn and Director of Principal Development for the KIPP Foundation. He co-led creation of the KIPP Framework for Excellent Teaching.
In 2000, he co-founded the third KIPP school in the country on a peanut field in Gaston, NC. He taught and led KIPP Gaston College Preparatory (GCP) for eight years. Under Caleb’s leadership, 100% of students in GCP’s first eight graduating classes were accepted to college with graduation rates above the national average and among the highest in the KIPP network.
Caleb began teaching in 1996 as a TFA a corps member in North Carolina at Gaston Middle School.