About this role
Hours:
- Sun & Monday 10:30 am – 7:00pm
- Tues-Thurs 2:30 pm – 11:00 pm
$21.00/hour | Meaningful Work | Predictable Routes
Driver CDL Required – Senior Living
Join The Clare, a luxury senior living community in downtown Chicago, and play a vital role in supporting residents’ independence, safety, and quality of life. As a CDL Driver, you’ll provide safe, reliable transportation for residents while working in a respectful, service-oriented environment—no freight, no long hauls, no overnight routes. Responsibilities include driving residents to scheduled appointments, maintaining the facility’s vehicle fleet and ensuring a clean, safe, and efficient transport experience.
If you’re a professional driver who enjoys working with older adults, values safety, consistency, and meaningful work, this role may be a great fit. If you're dependable, compassionate, and ready to make a meaningful impact, we’d love to hear from you.
Transportation Services
Collaborate with the Director of Resident Experience to manage and execute the campus transportation schedule.
Safely transport residents to medical appointments, social outings, and other scheduled destinations.
Maintain and operate community vehicles, ensuring they are in excellent working condition.
Follow DOT and passenger safety standards.
Fleet Maintenance & Cleanliness
Oversee the cleanliness and upkeep of all vehicles in The Clare fleet.
Ensure vehicles are regularly cleaned, waxed, and stocked with necessary supplies and equipment.
Professional Development & Teamwork
Stay current on transportation protocols and safety standards through ongoing training and in-service programs.
Uphold and promote the Mission and Values of the facility in all interactions.
Demonstrate a strong sense of teamwork, professionalism, and a positive attitude in daily operations.
Qualifications:
Must possess minimum of High School Education or equivalent. Language skills to read, write and speak in English.
1 year experience. Driving record must be acceptable to the community’s insurance standards. Current valid CDL
Benefits:
- Health, dental and vision insurance - begin the 1st of the month after your start date!
- 401(k) matching
- Bonus potential
- Employee assistance program
- Flexible spending account
- Life insurance
- Paid time off
- Referral program
- Tuition reimbursement
Other facts
About Cypress of Hilton Head
The Cypress of Hilton Head Island is an award-winning continuing care retirement community in the beautiful Lowcountry of South Carolina. Life at The Cypress springs into action on Hilton Head Island and within the secure-gated waterfront community, Hilton Head Plantation. The Preston Health Center at The Cypress Club of Hilton Head is a five-star, 62-bed health center providing services that include rehab, short term and long term stays and memory support.
What you'll do
- The CDL Driver will provide safe and reliable transportation for residents to various appointments and maintain the community's vehicle fleet. Responsibilities also include ensuring a clean and efficient transport experience.
Ready to join Cypress of Hilton Head?
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