Dean of Students- Upper School

Position Description

Job Title: Dean of Students – Upper School
Contract Term: Annual, 12-month (Flex Hours Eligible), Full Time
Reports To: Upper School Head
Start Date: 03 August 2026 (in prep for 2026-27 School Year)

Do you enjoy impacting the day-to-day and long-term lives of teenagers? Are you interested in partnering with parents in the nurturing of their children through intentional and relational mentorship? Do you desire an opportunity to help drive culture and mission through direct engagement with middle and high schoolers? Do you want to work amongst like-minded staff at a school committed to both academic and spiritual excellence? If so, read on!

Coventry Christian Schools, a classical Christian school of over 650 students located in Pottstown, PA, seeks an Upper School Dean of Students. This full-time, 12-month, flex-hours and benefits eligible position is a half-time administrative, half-time teaching position that is a key role in the Upper School. The selected candidate will be an integral part of the Upper School Admin Team and will oversee many important areas of student life, including the House System, student discipline, retreats and class trips, interscholastic academic competitions, and the Morning Devotions program. Strong people skills, demonstrated biblical wisdom, a heart for teenagers, and godly confidence are musts, as is the ability to maintain confidentiality. Prior experience working with teenage youth is essential, preferably in a school setting.

A full description of the position can be found here. After careful review of the position description, please spend time discussing the position with loved ones and seeking God’s guidance in prayer. If you remain interested after doing these things, you are warmly invited to submit a letter of interest and resume to Scott Dicken, Upper School Head, at [email protected].