Licensing and Compliance Lead in Bogotá at Heirloom

Heirloom exists to connect people to places and to each other. We design, build, and operate beautiful spaces that redefine what it feels like to travel as a group. With roots in New Orleans and a growing presence in more than a dozen destinations nationwide, Heirloom blends the warmth of hospitality with the power of technology to create unforgettable group travel experiences. Our focus on providing world-class accommodations in premier destinations, combined with a data-driven and tech-enabled operational strategy, has allowed Heirloom to carve out a distinctive position within the luxury short-term rental and property management space.

Compliance & Licensing Lead

General Overview

Overview:

This role sits within the Licensing & Compliance function and serves as a senior-level contributor responsible for managing complex, high-risk regulatory deliverables that are critical to maintaining operational continuity, legal compliance, and market access.

This individual operates with a high degree of autonomy, exercising sound judgment in navigating multi-jurisdictional licensing requirements, enforcement matters, and regulatory disputes. The role requires effective prioritization, rigorous documentation standards, and proactive risk mitigation to ensure the business remains fully compliant in all active markets.

Essential Functions:

• Own end-to-end case strategy and management for incident reports, regulatory inquiries, enforcement actions, review disputes, and payment disputes, ensuring timely, well-documented, and defensible submissions.
• Lead complex licensing initiatives, including new license applications, renewals, amendments, and jurisdictional expansions, overseeing document strategy, compilation, submission, and follow-through.
• Maintain and continuously improve internal licensing databases and compliance tracking systems to ensure audit-ready records and real-time visibility into regulatory status across markets.
• Proactively monitor code enforcement activity and internal case developments, identifying emerging risks and driving resolution with urgency and precision.
• Serve as a key partner to internal legal counsel on escalated matters, preparing comprehensive documentation packages, fact summaries, and supporting materials for legal review.
• Conduct structured audits of policy enforcement (including cancellation policies and related compliance obligations), identify inconsistencies, and lead corrective action initiatives.
• Develop and refine standardized documentation processes, submission protocols, and case tracking methodologies to enhance compliance reliability and operational efficiency.
• Lead cross-functional coordination with operations, finance, and legal stakeholders to ensure alignment on regulatory requirements and deadlines.
• Support high-impact special projects related to regulatory strategy, compliance infrastructure, and jurisdictional expansion.
• Special projects, as assigned.

Requisites

• Background: 3-5 years experience working in a paralegal or similar administrative support function for a U.S. based company.
• 3+ years experience supporting form filling and application submission for official licenses and permits.
• Fluent command of EnglishExcellent written and verbal communication skills: must provide writing sample
• Meticulously organized and detail oriented
• Experience with real estate law, land use, and zoning strongly preferred, but not required.

How to Apply

• Resume
• Brief cover letter that specifically addresses what you bring to the role you are applying for and what you would like to gain from the experience
• Please be prepared to submit a legal writing sample, it can be redacted if needed, preferably a memorandum and/or technical writing (1-3 pages in length max)
• A brief 60-90 minute technical writing assignment is administered as part of the interview process.