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Five-Minute Interview with Chief Advancement Officer Rick Henderson

Kelly Slonaker

Rick Henderson will be joining the Canterbury team as Chief Advancement Officer starting August 19, bringing extensive fundraising, consulting, and managerial experience to our advancement program.

Rick is currently the Vice President of Advancement at Fairfield College Preparatory School, where he has secured three of the school’s top four gifts of all time, including capital for an athletic center, a planned innovation center, and the first endowed chair in their school history. Additionally, Prep’s endowment has grown from $23 million to $35 million, and Rick has played an integral role in the school’s strategic planning process and marketing initiatives over his three-year tenure. Before joining Prep, Rick was Director of Major Gifts and Planned Giving at Choate Rosemary Hall. Prior to that, his entrepreneurial spirit served him well as president of Goal Line Philanthropy, a fundraising consulting firm, and president of Gift Annuity NOW™, a gift planning software company.

Outside his professional life, Rick is heavily involved in charitable activities in his hometown of Monroe, CT, where he resides with his wife Kim and their two children, Kylee and Cole.

While we eagerly await Rick joining us on campus next week, we wanted to share some fun facts about him with our community.


What do you find exciting about independent school advancement work?
I think for me, the best part is working with the full school-wide community; one of the advantages of advancement is getting to work with faculty, students, alumni, parents, and past parents. What I find most exciting is the opportunity to interact on a daily basis with every spoke in the wheel and every constituent that makes up the independent school community.

Another reason why I love doing what I do is to bring vision to life. What excites me about Canterbury is the vision of Rachel combined with an amazing and incredibly talented senior administrative team and faculty. I look forward to building onto all that Rachel and the team have given the campus. 

How many messages are in your inbox right now? 
[Laughs] Oh wow… 798. About 109 unopened.

What are you really into outside of work?
Being an ex-football coach, I do still have the coaching bug in me. I love coaching kids. Outside of that, my escape is running. I run everyday or every other day, it’s my best thinking time and best planning time. And I’ve got two kids ages 12 and 10 who keep me pretty busy.

Describe yourself in one word:
Relentless. 

What was your favorite subject in high school? 
For me, it was math.

What kind of student were you?
I was a good student. I graduated second in my class and was well-rounded. I was a football player, played saxophone in the band, ran track and field, and was on the student council. It was a great time!

What do you hope to achieve for Canterbury?
The definition of advancement is progress towards a goal. My job is to translate the School’s mission and ultimate goals for success to our alumni base and parents, and also to help bring these goals to life. That’s what gets me out of bed every morning: to achieve the goals of a school. That’s my number one purpose. What I hope to achieve for Canterbury is to apply my relentless approach to making sure that there’s no goal or dream that Canterbury feels is impossible to achieve.