VP, Head of Creative (Creative Director)

Position Title: VP, Head of Creative (Creative Director)

Reporting to: Chief Marketing Officer

Department: Creative

Location: Boston, MA (Hybrid)

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.

We’re looking for a VP, Head of Creative (Creative Director) to serve as the senior creative leader responsible for aligning creative strategy, brand stewardship, and operational excellence with Grand Circle Corporation’s growth agenda. This leader will guide the creative organization, drive high-impact customer-facing work, and partner across the business to ensure creative investments support measurable outcomes across acquisition, revenue growth, brand positioning, customer engagement, and conversion.

Key Responsibilities

• Lead creative strategies that directly support customer acquisition, revenue growth, brand positioning, and key business priorities, translating objectives into compelling customer-facing solutions.


• Establish the annual creative vision, roadmap, planning framework, and performance scorecard so major creative initiatives align to company growth priorities and measurable outcomes.


• Champion creative quality, consistency, and effectiveness across customer-facing channels while maintaining and evolving brand standards and governance.


• Use audience insights, creative testing, innovation, and emerging channels to improve engagement, conversion, campaign performance, and creative effectiveness.


• Build and lead a high-performing creative organization with clear roles, strong talent development, effective workload planning, and scalable resource management.


• Improve creative operating models, review and approval processes, prioritization, and resource planning to increase efficiency, accountability, and execution quality.


• Partner closely with Brand Marketing, DCX, NCA/Digital Marketing, Marketing Operations, Finance, Analytics, and senior leadership to support major acquisition, retention, product launch, campaign, and brand-building initiatives.

Qualifications

• 10 years’ experience leading and building teams in Creative


• Demonstrated senior creative leadership capability, with the ability to connect creative strategy and execution to business growth priorities.


• Strong brand stewardship and creative quality leadership across customer-facing marketing channels and touchpoints.


• Experience leading high-performing creative teams, including organizational design, talent development, workload planning, and resource management.


• Strong cross-functional partnership, testing, innovation, and performance-measurement capabilities, with the ability to establish scalable planning and governance frameworks.

Total Rewards
The base salary range for this role is $180,000 – $230,000 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

To learn more, please visit our websites at www.gct.com, www.oattravel.com and www.grandcirclefoundation.org.