Guest Compliance Manager

Windstar Cruises•Miami, FL

30d

About The Position

Awarded World’s Best Small Ship Cruise line, Windstar Cruises is known for its intimate yacht-style experience and unique voyages to the world’s best small ports and hidden harbors. Its three sailing yachts and four all-suite yachts carry just 148 to 342 guests and cruise around the world. Our mission is to imagine and deliver personalized and immersive experiences 180 degrees from ordinary. We enrich people’s perspective through inspired travel. Our Mission: Enriching Lives Through Travel Our Values: Guest Obsessed, Open and Inviting, Fun-Loving and Focused, Light-Hearted and Genuine, Casual Yet Polished, Safe and Responsible. The Guest Compliance Manager owns the intersection of guest protection, regulatory compliance, and travel protection revenue for Windstar Cruises' contact center. This is a uniquely broad management role requiring commercial acumen, regulatory fluency, and the interpersonal range to handle both sensitive guest escalations and cross-functional compliance leadership. The Guest Compliance Manager ensures that Windstar meets its legal and ethical obligations to guests across accessibility, data privacy, and travel documentation while simultaneously driving attachment revenue through the company's travel protection program. This role directly supervises Compliance Agents and operates as a key partner to the Senior Director in building a compliant, technology-forward contact center operation.

Requirements

3+ years of experience in compliance, operations management, or a related role within a travel, hospitality, or contact center environment.
Working knowledge of ADA regulations, PCI/PII standards, and travel documentation requirements across international itineraries.
Strong written and verbal communication skills, able to translate complex regulatory requirements into clear guidance for agents and leadership.
Empathetic and composed guest-facing presence, particularly in high-stakes or escalated situations.
Analytical and detail-oriented: comfortable owning reporting, documentation, and audit-readiness functions.
Enthusiasm for technology adoption; able to evaluate AI-assisted workflows through a compliance lens and provide constructive guidance.

Nice To Haves

Experience managing a revenue-generating product or program such as travel protection, insurance, or upsell preferred.

Responsibilities

Own the end-to-end travel protection program, including revenue targets, guest attachment strategy, monthly billing cycles, claims processing coordination, and accurate reporting across the contact center.
Serve as the organization's point of accountability for Americans with Disabilities Act accommodations, ensuring guests with accessibility needs receive appropriate, legally compliant support from booking through embarkation.
Maintain and enforce data protection protocols across all contact center touchpoints, ensuring PCI and PII standards are met consistently, including as new technology tools and workflows are introduced.
Own the accuracy and communication of international entry requirements, including passports, visas, vaccination documentation, and port clearances, reducing embarkation risk and guest disruption.
Serve as the escalation point for compliance-related guest issues including accessibility disputes, travel protection claims, documentation failures, and data handling concerns.
Directly supervise Compliance Agents, providing coaching, performance management, scheduling, and development in alignment with the department's quality and compliance standards.
Serve as the vendor relationship manager for travel protection, entry requirements, and other compliance related vendors.
Own the monthly reporting cadence for all compliance domains, including billing reconciliation, claims tracking, ADA case documentation, and incident logs, maintaining the records necessary to protect the company legally and operationally.
Partner with the AI Admin Lead to ensure AI-assisted workflows meet compliance requirements; serve as the compliance voice in technology adoption decisions.