Head of Compliance & Risk Management

Head Of Compliance & Risk Management

Reporting to:
Chief People Officer

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.

Grand Circle Corporation is seeking its first Head of Compliance & Risk Management 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 & Risk Management 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…