Field Operations Manager - Vacation Rentals (Cape Cod)

Company Description

Stay On The Cape is a boutique vacation rental management company specializing in high-quality homes across Cape Cod. We deliver hotel-level standards in private homes while building long-term relationships with homeowners and guests. We are a small, fast-moving company where strong operators can make a real impact and grow with us.

Role description

We are seeking a hands-on Field Operations Manager to oversee our Cape Cod homes and serve as the primary local contact for owners, vendors, and housekeeping teams. This role ensures properties operate smoothly during the busy season while driving improvements and projects in the off-season.

What you'll do

• Serve as the primary point of contact for Cape properties

• Conduct inspections and maintain company standards

• Oversee housekeeping quality and turnover readiness

• Manage supply ordering and inventory needs

• Coordinate maintenance and vendor scheduling

• Maintain strong homeowner relationships and communication

Off-Season focus

• Conduct property condition audits and spring readiness planning

• Oversee capital improvements and vendor coordination

• Review maintenance trends and prepare owner recommendations

• Serve as winter point person for off-Cape properties

• Assist with winter marketing and operational improvements

• Update home guides and improve property standards

Reservations & operational support

• Assist with messaging coverage during slower months

• Support the reservations team with guest communication tasks

Qualifications

• 3–5 years property management experience or operations leadership in hospitality, restaurants, or facilities management

• Strong organizational and operational instincts

• Experience managing vendors and field teams

• Calm, solution-oriented mindset

• Light maintenance and troubleshooting skills a plus

• If you have run a high-volume restaurant, led teams under pressure, and solved problems on the fly, you may already have the skill set this role requires.

Schedule

• This is not a traditional 9–5 role during peak season. Flexibility and responsiveness are essential during turnovers and busy weekends. Off-season months focus on planning and improvements.
• Must live on Cape Cod year-round
• Reliable transportation required

Compensation & growth

• $70,000–$85,000 based on experience, with performance bonuses and advancement opportunities as the company grows.

Additional benefits may include

• mileage reimbursement

• phone stipend

• flexible winter schedule

• opportunity to grow into regional leadership

• autonomy and decision-making authority