Managing Director

Job Title

Managing Director

Contemporary Staffing Solutions is seeking a Managing 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.

$65,000–$70,000 annually + benefits

Monday–Friday, normal business hours; schedule may vary based on bookings or operational needs

• 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

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.

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