Head of Compliance

Head of ComplianceReporting to: Chief People OfficerLocation: Boston, MA (Hybrid - 3 days per week in office)Position SummaryGrand 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 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.Key ResponsibilitiesEnterprise Compliance StrategyDevelop 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 GovernanceEstablish 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 & MonitoringDesign 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 PartnershipServe as the compliance leader and strategic partner across multiple domains, including:Information Security, Data Privacy, and Cybersecurity ComplianceFinancial Controls and Regulatory CompliancePayment and Transaction ComplianceEmployment Law and Workplace ComplianceTraveler Health and Safety StandardsQuality Assurance and Internal Operational StandardsVendor Management and Contract ComplianceCorporate Ethics and Business ConductTraining & Capability BuildingTrain 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 & ReportingEstablish 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.QualificationsRequired12+ 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.PreferredDeep expertise in at least one of the following disciplines:Data privacyInformation security complianceFinancial or payment complianceEmployment law complianceCorporate governance and ethicsInternal auditVendor and contractual complianceWorking knowledge across multiple compliance domains.Experience supporting global or multi-jurisdiction operations.Total RewardsThe 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 communityTo learn more, please visit our websites at and .Job SummaryRequisition Number: HEADO004465Job Category: DirectorSchedule: Full-Time