Digital Customer Experience Operations Specialist

Digital Customer Experience Operations Analyst

Reporting to: VP, Digital Platform Experience

Department: Digital Customer Experience (DCX)

Location: Boston, MA (Hybrid), Remote, or Other

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 talented DCX Operations Analyst to support the development and execution readiness of our website roadmap. Sitting within the DCX team, this role works closely with DCX leadership and partners with the Technology organization to translate priorities into clearly defined, actionable work. This role is ideal for someone with experience working alongside web or technology teams who can operate as a strong thought partner-bringing structure, clarity, and a customer-first perspective to digital initiatives.

Key Responsibilities

Web Roadmap Support & Alignment

• Support DCX Operations in driving and maintaining the website roadmap, ensuring priorities align with business objectives and traveler needs
• Help translate roadmap priorities into clearly defined, actionable initiatives ready for execution
• Maintain visibility into roadmap progress, dependencies, and readiness across teams

Requirements Quality & Experience Advocacy

• Review and refine requirements for website initiatives to ensure clarity, completeness, and alignment with intended outcomes
• Ensure user experience considerations and success criteria are clearly articulated before work enters execution
• Represent the voice of the traveler, asking thoughtful questions, identifying gaps, and challenging assumptions to strengthen solutions
• Actively participate in agile ceremonies to validate readiness and ensure work is well understood by all stakeholders

Decision Tracking & Operational Discipline

• Capture, document, and maintain key decisions, trade-offs, and action items across initiatives
• Establish and maintain clear tracking mechanisms to ensure decisions are visible and consistently followed through
• Drive accountability by proactively following up on open items, dependencies, and next steps

Cross-Functional Coordination

• Partner across DCX, Technology, Marketing, and other teams to ensure alignment on priorities, scope, and expectations
• Work closely with Technology Project Managers to ensure initiatives are clearly defined and positioned for successful execution
• Bridge communication between business and technical teams to reduce ambiguity and improve efficiency
• Surface risks, misalignment, or gaps early and help facilitate resolution

Qualifications

• 2-5 years of experience in digital operations, customer experience, marketing, product support, or a related field
• Experience working with website or digital teams and collaborating with technical stakeholders
• Familiarity with agile ways of working and participating in ceremonies such as backlog refinement or sprint planning
• Strong ability to review requirements, identify gaps, and improve clarity
• Excellent organizational skills with a proven ability to track decisions and drive follow-through
• Confident communicator who can ask questions, challenge assumptions, and advocate for the end user
• Ability to operate in a support capacity while contributing meaningful insight and structure

Preferred

• Experience working in a customer-facing digital environment (e.g., web, e-commerce, or digital platforms)
• Exposure to roadmap planning or prioritization processes
• Familiarity with tools such as Jira, Confluence, or similar

Total Rewards

The base salary range for this role is $85,000 - $95,000 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.