Field Operations Manager

About MyStay

MyStay is redefining luxury vacation experiences in Hilton Head Island by blending boutique hotel standards with the comfort and privacy of premium homes. As we expand our portfolio of high-end properties, we’re looking for a highly skilled Property Management Professional to protect, maintain, and elevate our homes to match the exceptional guest experience we’re known for.

Position Overview

We’re seeking a seasoned, hands-on Field Operations Manager to oversee the maintenance, standards, and daily condition of our growing portfolio of luxury homes.

This person must bring strong property knowledge, excellent organizational skills, and the ability to manage projects, vendors, and preventative maintenance without supervision. You’ll be responsible for ensuring every property meets MyStay’s signature high standards—every day, every guest, every owner.

Responsibilities

Field Operations & Property Oversight

• Conduct weekly and pre-arrival inspections of all luxury homes
• Identify maintenance issues before they escalate
• Ensure all homes meet MyStay’s strict cleanliness, safety, and aesthetic standards

Maintenance & Preventative Care

• Develop and execute preventative maintenance schedules
• Perform minor repairs, touch-ups, and hands-on tasks as needed
• Oversee pool, HVAC, landscaping, pest control, and appliance service cycles

Vendor Management

• Coordinate, schedule, and oversee all external vendors
• Build strong vendor relationships and negotiate pricing/response times
• Ensure all work is completed to high standards

Project Management

• Manage multiple property projects simultaneously
• Track renovation, upgrade, or seasonal prep work
• Communicate timelines and updates to the team and owners

Quality Assurance

• Walk homes after housekeeping and turnovers to ensure standards are met
• Report issues immediately and close loops fast
• Maintain documentation, logs, and checklists

Requirements

• 3–5+ years experience in high-end property management, hotel operations, or estate management
• Strong understanding of maintenance systems (HVAC, pool, plumbing, electrical)
• Hands-on fixer who is comfortable doing small repairs
• Exceptional organizational and communication skills
• Must be able to manage multiple simultaneous projects
• Clean, professional, guest-facing demeanor
• Ability to work flexible hours during peak check-in seasons
• Must thrive in a fast-growing, high-expectation environment

Who Will Succeed Here

Someone who takes ownership.
Someone who sees issues before anyone else does.
Someone who treats million-dollar homes as if they’re their own.
Someone who can be trusted to maintain excellence without being babysat.

This is the operational backbone of MyStay’s growth.

Pay: $50,000.00 - $60,000.00 per year

Benefits:

• Health insurance
• Paid time off

Work Location: In person