Head of Compliance

Location: Boston, MA (Hybrid - 3 days per week in office)

Position Summary

Grand Circle Corporation is the leader in international travel, adventure and discovery for Americans aged 50+. Headquartered in Boston MA, and with more than 35 offices globally, more than two million Americans have traveled with our award-winning travel brands: Grand Circle Cruise Line, Overseas Adventure Travel and Grand Circle Travel.

Key Responsibilities

Grand Circle Corporation is seeking its first Head of Compliance to establish and lead a comprehensive compliance program across the organization. Reporting to the Chief People Officer, this leader will partner closely with Information Security, Finance, People & Culture, Worldwide Operations, Contracting, Legal, and other business leaders to design and implement a global enterprise compliance framework that ensures adherence to internal standards, contractual obligations, regulatory requirements, and industry best practices.

This is a highly collaborative leadership role that succeeds through influence rather than direct authority. The Head of Compliance will create the governance structures, audit methodology, training programs, compliance metrics, and reporting processes necessary to build a culture of accountability and continuous improvement across multiple business functions.

The ideal candidate has successfully built or significantly transformed a compliance program in a complex organization, driven adoption across diverse business units, and developed audit and monitoring processes spanning multiple functional areas.

Enterprise Compliance Strategy

• Develop and maintain the company's global enterprise compliance strategy and roadmap.
• Create a scalable compliance framework that defines roles, responsibilities, controls, reporting requirements, and governance processes.
• Identify emerging compliance risks and partner with leadership to develop mitigation plans.
• Advise executive leadership on compliance trends, obligations, and program effectiveness.

Compliance Governance

• Establish a company-wide compliance operating model.
• Create and facilitate compliance governance forums and reporting mechanisms.
• Develop policies, standards, and controls in partnership with subject matter experts.
• Maintain enterprise compliance documentation and oversight processes.

Audit & Monitoring

• Design and implement a risk-based audit and monitoring program.
• Establish audit schedules, assessment methodologies, and corrective action tracking.
• Partner with functional leaders to conduct compliance reviews and remediation activities.
• Report audit findings, trends, and risk indicators to executive leadership.

Cross-Functional Partnership

Serve as the compliance leader and strategic partner across multiple domains, including:

• Information Security, Data Privacy, and Cybersecurity Compliance
• Financial Controls and Regulatory Compliance
• Payment and Transaction Compliance
• Employment Law and Workplace Compliance
• Traveler Health and Safety Standards
• Quality Assurance and Internal Operational Standards
• Vendor Management and Contract Compliance
• Corporate Ethics and Business Conduct

Training & Capability Building

• Train business stakeholders to execute compliance responsibilities effectively.
• Together with business stakeholders, promote a culture of accountability, transparency, and ethical conduct.
• Ensure compliance responsibilities are embedded within business processes, leadership expectations and stakeholder Key Result Areas.

Metrics & Reporting

• Establish compliance KPIs and control effectiveness measures.
• Develop enterprise compliance dashboards.
• Track trends, findings, remediation progress, and risk indicators.
• Present regular compliance updates to senior leadership.

Qualifications

Required

• 12+ years of progressive compliance, risk, audit, governance, legal, regulatory, or related experience.
• Experience building or significantly enhancing a compliance program from the ground up.
• Demonstrated success driving enterprise-wide adoption through influence rather than direct authority.
• Experience creating audit methodologies and compliance monitoring programs.
• Ability to partner effectively with executive leadership and cross-functional teams.
• Strong understanding of compliance governance, risk assessment, internal controls, and policy development.
• Excellent communication, facilitation, and stakeholder management skills.

Preferred

• Deep expertise in at least one of the following disciplines:
• Data privacy
• Information security compliance
• Financial or payment compliance
• Employment law compliance
• Corporate governance and ethics
• Internal audit
• Vendor and contractual compliance
• Working knowledge across multiple compliance domains.
• Experience supporting global or multi-jurisdiction operations.

Total Rewards

The base salary range for this role is $185,000 – $235,000 annually for employees based in Boston, MA. Final compensation may vary and will be determined based on factors such as relevant experience, skills, internal equity, and geographic location. In addition to base pay, this role is eligible for an annual incentive bonus and first-class benefits, which include:

• Health & wellness: Comprehensive and heavily subsidized medical, dental, and vision plans, plus on-site gym access, holistic wellness sessions, and group fitness classes
• Time for you: Substantial Paid Time Off (PTO), and 11 paid holidays- including Juneteenth, Memorial Day, and Labor Day – and Summer Fridays. Plus- extensive parental leave, with up to 12-16 weeks paid leave at 100% base salary.
• Travel more, spend less: 50% off our trips for you and a companion, 25% for additional immediate family members, and exclusive quarterly associate travel deals
• Your future, secured: 401(k) with company match, life insurance, and disability coverage
• Continuous growth: Tuition assistance for both professional and personal development, opportunities for professional development through oversees travel, and direct access to Pinnacle Leadership & Team Development.
• Extra perks: Commuter benefits, FSA options, pet insurance, home & auto discounts, and paid volunteer time off to give back to the community

Equal Opportunity Employer

This employer is required to notify all applicants of their rights pursuant to federal employment laws.For further information, please review the Know Your Rights notice from the Department of Labor.