Director of UX & Web Design

Director of UX & Web Design

Reporting to: EVP, Digital Customer Experience
Department: Digital Customer Experience
Location: Boston, MA (Hybrid/Remote)

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 45 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 Director of UX & Web Design to set the vision and standards for the GCC web experience and lead the evolution of our digital customer journeys from trip discovery through booking. This role oversees UX, UI, web design, and research, ensuring that our experiences reflect traveler needs while driving measurable business outcomes.

This leader operates as both a strategic thought partner and a hands-on design leader, balancing design excellence with operational realities. They partner closely with Digital, Creative, Brand, and Analytics teams to ensure our web experience builds trust, communicates value clearly, and supports scalable growth across O.A.T. and GCT.

Key Responsibilities

• Define and own the end-to-end UX strategy and roadmap for O.A.T. and GCT, with a focus on trip discovery, booking flows, value clarity, and brand trust


• Lead the team in delivering best-in-class digital experiences tied to measurable outcomes, including conversion, funnel progression, and reduced abandonment


• Build, mentor, and scale a high-performing UX, UI, and Web Design team; establish design standards, feedback rituals, and clear career paths


• Champion inclusive design and accessibility standards, ensuring intuitive experiences for our 50+ traveler audience across devices


• Partner with Web Operations, Brand Marketing, Creative, and Data/Analytics to translate insights into actionable design decisions


• Establish evidence-based design practices, including A/B testing, usability testing, and session reviews, to continuously optimize the booking funnel


• Communicate design rationale, tradeoffs, and outcomes to executive and cross-functional stakeholders


• Govern the full design lifecycle, from research and discovery through implementation and QA


• Own and evolve the Figma-based design system to ensure consistency, scalability, and strong component standards


• Stay current on emerging UX and digital trends to differentiate GCC brands


• Lead on-site digital design for marketing campaigns and promotions, ensuring alignment with brand standards and conversion goals

Qualifications

• 7–10+ years of experience in UX, UI, or Product Design, with 5+ years leading and developing design teams


• Proven track record building and governing design systems and delivering complex, content-rich web experiences


• Experience in travel, eCommerce, or similarly complex digital environments


• Deep expertise in UX principles, interaction design, responsive web design, and accessibility standards


• Fluency in Figma and modern design operations practices


• Strong communicator with experience presenting to executive audiences and aligning cross-functional stakeholders

Total Rewards

The base salary range for this role is $150,000 – $165,000 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 overseas 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