AUGUST 20 • 2020 | 21

A

s a former student who 
began his academic career 
in the public schools 
outside of Boston but then transi-
tioned to a private school environ-
ment, Rich Dempsey knows the 
transformative power of a private 
school education.
“There were doors that opened 
that I never knew existed,
” he 
said about his attendance at St. 
George’
s School in Newport, 
R.I. “The relationships and con-
nections students had with each 
other and adults in that commu-
nity were extraordinary. That’
s 
true for every private school. It 
was magnetic.
”
Now, Dempsey plans to share 
that experience with students 
at Detroit Country Day School 
in Beverly Hills. Dempsey, the 
former Associate Head of School 
at Pomfret School in Pomfret, 
Conn., has taken over leader-
ship of Detroit Country Day as 
Head of School, effective July 1. 
He replaces Glen Shilling, who 
served as Headmaster since 2007.
Dempsey has 24 years of 
administrative and teaching 
experience in independent day 
and boarding schools. He began 
his career in education as chem-
istry and math teacher at St. 
George’
s, where he also served 
as an advisor, dorm parent and 
head coach of hockey and base-
ball. He also held leadership and 
administrative positions, includ-
ing Director of Summer Session 
and Associate Dean of Students, 
while continuing to teach in the 
classroom.
When Dempsey, his wife 
Mary and their seven-year-old 

son Teddy were looking to make 
a move, Dempsey said he did 
a national search for his next 
career opportunity, ideally as 
head of a private school. 
“I wanted to be the head of the 
right school, a school that had an 
extraordinary educational com-
munity,
” he said. “I wanted to not 
only work with older students 
but with younger students too. I 
wanted to find that school that I 
felt prepared kids best.
”
Dempsey found that in 
Detroit Country Day, which was 
established 106 years ago by F. 
Alden Shaw, a Harvard-educated 
Minnesotan who wanted to 
create a school that emphasized 
academic rigor and preparedness 
for higher education as well as 
the immersion of students in 
athletics and the arts. DCDS stu-
dents also draw on the school’
s 
traditions of character-building, 
mutual respect among them-
selves and faculty, and the skills 
to embrace social and personal 
responsibility.
Dempsey began working with 
school administrators and staff 
in March. He said he recalls his 
visit to DCDS in May 2019 as a 
finalist for the position.
“One can only be over-
whelmed by the warmth and 
strong sense of community that 
we have here at Detroit Country 
Day,
” he said, characterizing 
those he met as “real, authentic 
and genuine.
”
“This school community 
embraces tradition while also 
evolving, modernizing and 
accepting change,
” he said.
As Head of School, Dempsey 

says he’
ll be drawing on his expe-
rience at Pomfret School, as well 
as his time spent at Rocky Hill 
School in East Greenwich, R.I., 
where he served as Head of the 
Upper School for five years. 
Dempsey graduated from 
Bowdoin College with a bach-
elor’
s degree in biochemistry 
and extensive work in English. 
He earned a Master’
s of 
Education Degree in Educational 
Administration from Boston 
University and completed 
a National Association of 
Independent Schools Fellowship 
for Aspiring Heads of School.
Dempsey’
s vision for the 
current and future Detroit 
Country Day School is one 
focused on students rather than 
a teacher-based model empha-
sizing lectures.
“Education must switch to … 
one that focuses on the individ-
ual student and is skills based 
and content rich,
” he said. “The 
skills-focused model that schools 
need to follow will allow for 
students to develop skills includ-
ing learning to think critically, 
how to be creative, how to be a 
strong communicator, how to be 
a thoughtful listener, and how to 
be able to champion your own 
ideas. That’
s critical in this day 
and age.
”
Dempsey said it’
s also impera-
tive to prepare kids for jobs that 

don’
t exist yet, and to impart the 
knowledge that today’
s world is 
much more diverse and inter-
connected. He wants to promote 
deeper and more meaningful 
learning experiences and an 
education that is both thoughtful 
and project based.
Like all schools, Detroit 
Country Day has had to adapt 
to the current coronavirus pan-
demic. Dempsey sees this as not 
only an opportunity to assimilate 
to the rapidly changing times but 
to embrace the moment as an 
opportunity to look long term at 
DCDS’
s future.
“We need to shift our practice 
to provide more enhanced edu-
cational opportunities for our 
students,
” he said. “We recognize 
that this is a moment to step 
back and evaluate thoroughly 
our student experience from the 
perspective of their well-being, 
resiliency, and perseverance. 
It is also time to reflect on our 
empathy for and appreciation of 
others. This moment calls for us 
to reinvent, pivot and make an 
even better overall experience for 
all our students.
”

Detroit Country Day 
School welcomes 
Rich Dempsey as new 
Head of School

BY ELIZABETH KATZ

SPONSORED BY DETROIT COUNTRY DAY SCHOOL

DETROIT COUNTRY DAY SCHOOL

22305 West 13 Mile Road

Beverly Hills, MI 48025

248.646.7717

dcds.edu

LINDSAY LEHMANN