888-815-4571 Concierge
843-547-2003 Sales


Current Opportunities

This Hardly Feels Like Work

Find Your Purpose in Paradise.

At The Cypress of Hilton Head, you have the opportunity to make a meaningful difference in the lives of our senior members while working in an ideal, resort-style setting. While our island vibe sets everyone at ease, our hard-working employees help set our community apart. 

Join our team and experience the unique satisfaction of doing important work in a picturesque place. It’s hard to be in a bad mood at The Cypress, which makes it a fantastic place to work. 

Career Path Found

Working at The Cypress gives you access to a fulfilling and lasting career. While it’s important to bring passion and dedication to our members each day, we understand you also have your own aspirations. For that reason, we foster a supportive environment for our employees, with ample advancement opportunities and various benefits that help you keep work and life in balance.


Satisfaction. In and Out of Work.

WHOLE-FAMILY HEALTHCARE------------------------------------

The Cypress’ comprehensive employee healthcare program provides welcome peace of mind for you and your family. Enjoy access to multiple providers plus dental, vision, and prescription medication coverage.

EMPLOYEE DISCOUNTS------------------------------------

Thanks to an agreement between The Cypress and some of its valued vendors, Cypress employees enjoy exclusive deals on products and services ranging from plumbing fixtures to rental cars.

401(K) PLAN------------------------------------

We are committed to helping our employees create a financially secure future with a robust 401(k) plan. Full-time employees with over a year of service at The Cypress are eligible to enroll.

PAID TIME OFF------------------------------------

Recharging your batteries is an important practice for Cypress employees. That’s why we offer full-time employees a generous amount of time to use for vacation, doctor’s appointments, school plays, and other needs.

EMPLOYEE ASSISTANCE PROGRAM------------------------------------

To help our employees maintain a positive work-life balance, The Cypress makes several essential life services available free of charge. These include financial consulting, psychological counseling, and childcare resources.

LIFE INSURANCE------------------------------------

The Cypress offers all full-time employees Basic Life and Accidental Death and Dismemberment (AD&D) insurance, providing you and your family with extra financial security.

Celebrating Our Differences

At The Cypress, we’ve worked hard to create a respectful and inclusive culture that mirrors the diversity of the members we serve. Our hiring practices reflect our commitment to employee excellence, regardless of age, race, and gender. We welcome applicants from all walks of life to join our team and continue helping us cultivate a community that celebrates everyone.

African home nurse helping woman in wheelchair with hand weight

More To Make You Happy

Employee recognition and rewards
Employee and dependents scholarship program
Quarterly employee and holiday events
Employee referral program
Committed leadership
A friendly, family atmosphere

“I love my residents, that’s what makes me come back to work every day. Also, The Cypress gives the opportunity to grow. I love what I do.”

Merci Blake

Billing Coordinator, 29 Years of Service

“It’s a special place to work.”

Mia Hughey

Human Resources, 5 Years of Service

“It feels like an extended family at work.”

Rasa Wilder

Human Resources, 13 Years of Service

“I enjoy working with elderly people. Great coworkers.”

Kris Linsday

Concierge, 3 Years of Service

“It doesn’t feel like a job with a family atmosphere.”

Heidi Hanson

Fitness Coordinator, 16 Years of Service

“I love to help my elderly members. I feel like I have a purpose with our family atmosphere.”

Cindy Binkley

Hilton Head Scheduler, 7 Years of Service

“Very friendly and nice environment to work. Wonderful people.”

Robert Thompson

Driver, 11 Years of Service

“I love my residents and coworkers. I am passionate about [my job].”

Marilyn Ireland

CNA, 8 Years of Service

“I like my members and staff. Good environment and nice place to work.”

Jamil Young

Lead Cook, 23 Years of Service

“Good environment. Nice people; it’s a good place to work.”

Chris Elliott

Utility Technician/Dishwasher, 22 Years of Service

“I love working with elderly people and listen[ing] to their life stories.”

Juanita Major

Dining Room Supervisor, 10 Years of Service

your-life-better illustration