Vacation Rental Remote Compliance Manager (Remote, PH-Based)

Full-Time Remote Compliance Manager (Remote, PH-Based)

Compensation: $900-$1100 monthly depending on experience

Reports to: VP of Operations

About Fieldtrip:

Fieldtrip (stayfieldtrip) is a luxury hospitality + real estate firm specializing in premium branded short-term rentals (Airbnbs). We’re the leading boutique hospitality brand in the luxury short-term rental space, currently operating over $200M in luxury homes and boutique hotels. Our collection includes the world-famous Invisible House, as well as one of the nation’s largest custom-built Airbnb portfolios.

Hospitality is at the core of what we do. Our Guest Experience team provides prompt support and curates bespoke travel experiences and immersive activities. The quality of our white-glove service is evident in our 4000+ 5-star ratings.

What We're Looking For:

We are seeking a detail-oriented and proactive Remote Compliance Manager to oversee short-term rental compliance across our diverse property portfolio. This role is ideal for a candidate with paralegal experience who can effectively communicate with U.S.-based jurisdictions to ensure our properties adhere to local permitting laws and insurance requirements.

Key Responsibilities:

Permit & Tax Compliance: Manage short-term rental permit applications, renewals, and transient occupancy tax (TOT) certificate processes across various U.S. jurisdictions.

Insurance Oversight: Monitor homeowner insurance policies for compliance, track expiration dates, and coordinate renewals to maintain continuous coverage.

Regulatory Liaison: Interface with U.S.-based jurisdictions via email and phone to address compliance inquiries and resolve issues promptly.

Documentation & Reporting: Maintain accurate records of all compliance-related activities and provide regular updates to the VP of Operations.

Process Improvement: Identify areas for operational enhancement within compliance workflows and collaborate with cross-functional teams to implement improvements.

Requirements:

Located in the Philippines and available to work in U.S. time zones (or partial overlap).

Paralegal certification or equivalent legal background highly desired.

Minimum of 2 years' experience in compliance management, legal administration, or related fields.

Familiarity with U.S. short-term rental regulations and permitting processes.

Strong written and verbal communication skills, with the ability to engage effectively with U.S. jurisdictions.

Proficiency in Microsoft Office Suite (Word, Excel, Outlook) and Google Workspace.

Exceptional organizational skills and attention to detail.

Ability to work independently and manage multiple tasks simultaneously.

Bonus and Benefits:

13th Month Bonus

Paid Time Off, such as PTO, Sick days, and Vacation days

Health Insurance

IMPORTANT:

Please read the instructions carefully before applying.

This role requires strong attention to detail—and that begins with how you apply.

To be considered, all required materials must be submitted in full at the time of application.

Incomplete submissions will not be reviewed.

If you’re not yet ready to submit all items, we kindly ask that you wait until you are.

This ensures fairness and helps us keep the process efficient for everyone.