Managing & Retreats Director
Operations Rehoboth Beach, Delaware
Direct Hire Feb 2, 2026
Operations
Job Title: Managing & Retreats Director
Job Overview:
Contemporary Staffing Solutions is seeking a Managing & Retreats Director to join our client and oversee the full operational and guest-experience lifecycle of a coastal retreat property. This key leader will guide strategy, financial stewardship, staffing, and day-to-day operations to ensure a seamless environment for groups, guests, and returning visitors. Based in Rehoboth Beach, DE, this hybrid, direct-hire position blends administrative leadership with hands on oversight of hospitality operations. The ideal candidate thrives in a mission driven setting, enjoys building strong relationships, and can balance strategic planning with on site management.
Compensation:
$65,000–$75,000 annually + benefits
Work Schedule:
Monday–Friday, normal business hours; schedule may vary based on bookings or operational needs
Key Responsibilities of the Managing & Retreats Director:
This role offers the opportunity to make a meaningful impact on a long-standing, guest-focused destination known for returning visitors and community connection. You’ll collaborate with dedicated teams, shape operational excellence, and lead a unique hospitality environment. Candidates are also invited to stay onsite before starting to experience the property firsthand.
About Us:
Contemporary Staffing Solutions (CSS) is a trusted leader in providing contract, temporary, temp-to-hire, and direct hire staffing solutions. With decades of experience, we’ve grown from a staffing agency to a nationwide provider of workforce management solutions. Our niche recruitment expertise spans Accounting & Finance, Call Center & Office Support, Human Resources, Sales & Marketing, and Information Technology. Explore more about CSS and how we connect great talent with exceptional opportunities by visiting www.ContemporaryStaffing.com.
Job Overview:
Contemporary Staffing Solutions is seeking a Managing & Retreats Director to join our client and oversee the full operational and guest-experience lifecycle of a coastal retreat property. This key leader will guide strategy, financial stewardship, staffing, and day-to-day operations to ensure a seamless environment for groups, guests, and returning visitors. Based in Rehoboth Beach, DE, this hybrid, direct-hire position blends administrative leadership with hands on oversight of hospitality operations. The ideal candidate thrives in a mission driven setting, enjoys building strong relationships, and can balance strategic planning with on site management.
Compensation:
$65,000–$75,000 annually + benefits
Work Schedule:
Monday–Friday, normal business hours; schedule may vary based on bookings or operational needs
Key Responsibilities of the Managing & Retreats Director:
- Lead operational, financial, and strategic management of the retreat property
- Oversee staff leadership, vendor coordination, and facility upkeep
- Manage guest onboarding, bookings, and overall retreat scheduling
- Guide budgeting, performance management, and administrative processes
- Partner closely with organizational leaders and internal teams to ensure high-quality service
- Prior leadership experience in hospitality, property management, or retreat operations
- Strong financial management and budgeting skills
- Ability to manage staffing schedules, performance processes, and vendor relationships
- Excellent communication and customer-focused problem solving abilities
- Comfortable working in a hybrid role with occasional on-site needs
This role offers the opportunity to make a meaningful impact on a long-standing, guest-focused destination known for returning visitors and community connection. You’ll collaborate with dedicated teams, shape operational excellence, and lead a unique hospitality environment. Candidates are also invited to stay onsite before starting to experience the property firsthand.
About Us:
Contemporary Staffing Solutions (CSS) is a trusted leader in providing contract, temporary, temp-to-hire, and direct hire staffing solutions. With decades of experience, we’ve grown from a staffing agency to a nationwide provider of workforce management solutions. Our niche recruitment expertise spans Accounting & Finance, Call Center & Office Support, Human Resources, Sales & Marketing, and Information Technology. Explore more about CSS and how we connect great talent with exceptional opportunities by visiting www.ContemporaryStaffing.com.