What are the responsibilities and job description for the Field Operations Supervisor position at InsideOut Properties of Cape Cod?
Field Operations Supervisor
Housekeeping Leadership Role
Outer Cape Cod
We are a boutique, award winning vacation rental company located in Eastham on the outer Cape, and we are looking for a confident, detail driven Field Operations Supervisor to support our housekeeping operations year round.
This role is primarily a field leadership position, especially during our busy season, when supervising teams, ensuring quality, and keeping operations running smoothly is critical. In the off season, when teams are smaller, this role shifts to include more hands on cleaning while still maintaining responsibility for driving, oversight, and Breezeway checklists.
This position is ideal for someone who is comfortable leading others, values high standards, and understands the seasonal nature of hospitality work.
What you will do
- Lead and support housekeeping teams in the field
- Drive the team to assigned properties using company vehicles
- Direct workflow, assign tasks, and keep the day moving efficiently
- Ensure all homes meet company standards using our Breezeway checklist system
- Perform final walkthroughs and sign off on homes
- Restock guest amenities and supplies as needed
- Report damages, maintenance issues, and concerns clearly with photos and notes
- Act as the liaison between housekeeping, maintenance, and the home office
- Maintain a clean, stocked, and professional work vehicle
- Help keep teams focused, supported, and working well together
- Redirect work when tasks are missed or standards are not met
You may assist with cleaning and touch ups when needed, especially in the off season, but quality control, organization, and accountability remain core responsibilities year round.
Schedule and seasonality
- Typical start time is between 8:30 and 9:00 AM
- This is a year round position with seasonal variation in hours
- During peak season, hours are full-time consistent and leadership focused
- During the off season, supervisors often take on more cleaning as teams are smaller
- Some winter weeks may be light, with limited days of work depending on reservations
What we are looking for
- Comfortable directing and supervising others
- Confident addressing strong personalities and redirecting work when needed
- Detail oriented and checklist driven
- Comfortable communicating and working across multiple languages and cultural backgrounds
- Calm under pressure and able to keep teams focused
- Reliable, organized, and accountable
- Valid driver’s license and comfort driving company vehicles
- Previous experience leading, supervising, or directing others in a work setting is required
- Prior housekeeping or hospitality experience preferred
Benefits
- Flexible schedule
- Dental
- Vision
- TeleHealth
- Rx Discounts
- Accident
- Short Term Disability
- Long Term Disability
- Critical Illness
- Term Life Insurance
- Whole Life Insurance
- 401(k)
- Employee Discount Programs
Compensation
- Competitive hourly pay based on experience, starting in the low $20’s per hour
- Seasonal retention bonus
Why work with us
Our housekeeping teams have received industry recognition, including a prestigious VRMA award for excellence. We take pride in our standards, our people, and the systems that support them. This role plays a key part in maintaining quality and supporting both our teams and our guests.
If you enjoy leading in the field, value organization and standards, and are looking for a role that evolves with the seasons, we would love to hear from you.
Job Types: Full-time, Part-time
Pay: From $20.00 per hour
Expected hours: 8 – 40 per week
Work Location: In person
Salary : $20