Head Counselor Caddie Program
Listed on 2026-01-08
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Education / Teaching
Summer Seasonal, Youth Development
The Daniel Murphy Scholarship Fund (DMSF) is Chicago’s largest high school scholarship organization serving high potential students from limited resourced communities. DMSF provides financial and programmatic support to scholars to attend and excel at top tier high schools in the Chicago area and at boarding schools around the country.
Job DescriptionDMSF seeks to hire two Head Counselors for its Caddie Program
. The Caddie Program allows student scholars to gain job experience, earn money, improve communication skills, and potentially apply for the Chick Evans Scholarship- a full tuition and housing scholarship for high-achieving caddies with limited financial means.
The Head Counselor has overall responsibility for the Scholars who participate in the summer Caddie Program. The job entails living with the Scholars in the dorm, transporting them to work in the morning (in vehicles provided by DMSF), picking them up at the conclusion of their work day, and supervising them for the balance of the day. The Head Counselor will typically have free time between 9am - 2pm, as well as from Sunday evenings until Tuesday mornings, when most Scholars go home.
DMSF anticipates hiring educators, teachers, or college/graduate students to serve as Assistant Counselors.
DMSF seeks to hire two Head Counselors for the Caddie Program, one for the boy’s program and one for the girl’s program.
Responsibilities- Living in dorms with Scholars
- Ensuring the Caddies are routinely transported to and from work each day
- Supervising Scholars while at the dorms and coordinating weekly activities, such as guest speakers, social events, and workshops
- Transporting Scholars to and from weekly First Tee programming to learn the game of golf
- Providing Scholars transportation to trains on Sunday afternoon and from trains on Tuesday morning if their clubs are not accessible to the station
- Maintaining records of tips and loops per Caddie
- Maintaining all logistics related to food service and vehicle maintenance (e.g. ensuring vehicles have gas)
- Enforcing DMSF policies and procedures
- Reporting to DMSF on a regular basis about Scholars and the program
- Communicating with parents as it relates to Scholar transportation logistics, behavior, illness, or free time activities, etc.
- Experience working with and supervising young adults
- Excellent supervisory and communication skills
- Valid driver’s license and an infraction‑free driving record for the past two years
- General understanding of the game of golf and caddying is helpful but not required
DMSF is an organization that prioritizes workplace culture, collaboration, timely and thorough communication and effective project management.
All your information will be kept confidential according to EEO guidelines.
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