Dr. Jay Simpson
(He/Him/His)

Dr. Jaykyri Simpson is the Executive Director of Young Man with a Plan, a holistic mentoring program serving young Black and Latino men “in the middle” across 8 Boston schools. Under Jaykyri’s leadership, YMWAP has grown from a small program serving 20 students to a 501c3 organization serving over 200 students and alumni in a unique mix of in- and after-school mentoring and success planning.

In 2021 Jaykyri received his doctorate in Educational Leadership from New England College where his dissertation research, “Persistence Factors in Black Male College Graduates,” affirmed the value of mentoring and the degree to which young Black men crave explicit guidance respectfully delivered by trusted people. Jaykyri incorporates everything learned through his research into YMWAP’s curriculum.

Prior to leading YMWAP, Jaykyri launched Project Ochendo at New Mission High School in Boston, where he taught and mentored students of color, helping them improve study skills and grades, and to access and persist at college. He also served as basketball coach, admissions counselor, and retention coordinator for three years at Mt. Ida College and as basketball coach for two years at the University of New England (UNE). Jaykyri also has a deep connection to sports. He played college basketball for all four years, starting at a small junior college in Texas and transferring to the University of New England and Maine to finish his collegiate career. In addition to coaching on the collegiate level, Dr. Simpson has coached high school football at New Mission High for a few years.

Jaykyri was in the 2020 cohort of the Lewis Family Foundation’s Strong Leader Program and the 2021 TSNE Nonprofit Executive Directors of Color Program. He was named a 2022 Social Innovation Forum Innovator and Institute for Nonprofit Practice Changemaker. Jaykyri is a member of EdVestor’s Racial Equity Task where he leads teacher dialogues on effectively engaging young men of color in the classroom. He has been a consultant and guest educator at New England College. Jaykyri has presented at The Possible Zone, the Massachusetts Black and Latino Legislative Caucus, Life Science Cares, Social Innovation Forum, Boston Beyond, The Philanthropy Connection, EdVestors, Third Sector New England, and at CT Rise and Teacher Powered Schools Conferences. Most recently, The New Commonwealth Fund recognized YMWAP’s deep community impact by inviting the organization to participate in a state-funded maternal health equity public health initiative.

Jaykyri received his B.A. at UNE where he captained their division-winning basketball team and he earned his MBA from St. Joseph’s College in Maine. Originally from Cleburne, Texas, Jaykyri is a founding member of Men on a Mission, a nonprofit in his hometown.