Director of UX & Web Design

📍 Job Overview

Job Title: Director of UX & Web Design

Company: Grand Circle Corporation

Location: Boston, MA

Job Type: Full-Time

Category: UX/UI & Web Design Leadership

Date Posted: March 27, 2026

Experience Level: Senior / Director

Remote Status: Hybrid/Remote

🚀 Role Summary

• This leadership role is pivotal in shaping the digital customer experience for Grand Circle Corporation's travel brands, focusing on UX strategy and web design excellence.

• Responsible for defining and executing the end-to-end UX strategy and roadmap, with a strong emphasis on trip discovery, booking flows, and enhancing brand trust.

• Drives measurable business outcomes through superior digital experiences, including increased conversion rates and reduced customer abandonment.

• Leads and mentors a high-performing UX, UI, and Web Design team, establishing robust design standards and fostering clear career development paths.

• Champions inclusive design and accessibility to cater to the 50+ traveler demographic across all digital touchpoints.

📝 Enhancement Note: While the title is Director of UX & Web Design, the responsibilities and reporting structure (reporting to EVP, Digital Customer Experience) indicate a significant strategic and leadership component, aligning with a senior operations or GTM leadership function focused on digital customer acquisition and retention. The emphasis on measurable outcomes (conversion, abandonment) and cross-functional partnership (Digital, Creative, Brand, Analytics, Web Operations) firmly places this role within a GTM operational framework.

📈 Primary Responsibilities

• Define and own the comprehensive UX strategy and roadmap for Overseas Adventure Travel (O.A.T.) and Grand Circle Travel (GCT), with a strategic focus on optimizing the trip discovery phase, streamlining booking flows, clarifying value propositions, and reinforcing brand trust.

• Lead the UX, UI, and Web Design team in the development and delivery of best-in-class digital experiences, directly contributing to key performance indicators such as website conversion rates, customer funnel progression, and significant reductions in cart or booking abandonment.

• Build, mentor, and scale a high-performing UX, UI, and Web Design team; establish rigorous design standards, implement effective feedback rituals, and define clear, actionable career paths to foster professional growth and retention.

• Champion and implement inclusive design principles and accessibility standards (WCAG compliance), ensuring that digital experiences are intuitive, user-friendly, and accessible for the target demographic of travelers aged 50+ across all devices and platforms.

• Foster strong collaborative partnerships with Web Operations, Brand Marketing, Creative teams, and Data/Analytics to effectively translate user insights, business requirements, and performance data into actionable, data-informed design decisions and optimizations.

• Establish and maintain evidence-based design practices, leveraging methodologies such as A/B testing, multivariate testing, usability testing, and session recording analysis to continuously iterate and optimize the critical booking funnel and overall customer journey.

• Articulate and communicate complex design rationale, strategic tradeoffs, and the quantifiable outcomes of design initiatives to executive leadership, cross-functional teams, and other key stakeholders through compelling presentations and clear documentation.

• Govern the entire design lifecycle, from initial user research and discovery phases through to final implementation, quality assurance (QA), and post-launch performance monitoring, ensuring a cohesive and efficient design process.

• Own, manage, and continuously evolve the Figma-based design system, ensuring its scalability, consistency, and the maintenance of strong component standards to support efficient design and development workflows across multiple brands and platforms.

• Stay abreast of emerging UX trends, digital technologies, and best practices within the travel and leisure industry to identify opportunities for innovation and to strategically differentiate Grand Circle Corporation's brands in the competitive market.

• Lead the on-site digital design efforts for marketing campaigns, promotional activities, and new product launches, ensuring strict alignment with brand standards, marketing objectives, and critical conversion goals to maximize campaign effectiveness.

📝 Enhancement Note: The responsibilities highlight a blend of strategic leadership, team management, and hands-on design oversight. The emphasis on "measurable outcomes," "conversion," "funnel progression," and "reduced abandonment" points to a strong GTM operations focus. The need to "govern the full design lifecycle" and "evolve the Figma-based design system" indicates a need for process rigor and operational efficiency in the design function.

🎓 Skills & Qualifications

Education: While not explicitly stated, a Bachelor's degree in Graphic Design, Human-Computer Interaction (HCI), Digital Media, or a related field is typically expected for a Director-level UX role. Advanced degrees or relevant certifications in UX research methodologies or design leadership are advantageous.

Experience: 7–10+ years of progressive experience in UX, UI, or Product Design, with a minimum of 5 years specifically focused on leading and developing design teams. Demonstrable experience in managing complex, content-rich web experiences and building/governing design systems is crucial. Experience within the travel, eCommerce, or similarly intricate digital commerce environments is highly preferred.

Required Skills:

• UX Strategy & Vision: Ability to define and articulate a clear, long-term UX strategy and roadmap aligned with business objectives for discovery and conversion.

• Team Leadership & Development: Proven success in building, mentoring, and scaling high-performing UX/UI design teams, including establishing career paths and performance management frameworks.

• Design System Governance: Expertise in creating, maintaining, and evolving robust design systems (specifically Figma-based) to ensure consistency, scalability, and efficiency across digital products.

• User Research & Testing: Deep knowledge of user research methodologies, including usability testing, A/B testing, session analysis, and translating findings into actionable design improvements.

• Accessibility & Inclusive Design: Strong understanding and practical application of WCAG standards and inclusive design principles to cater to diverse user needs, particularly the 50+ demographic.

• Figma Proficiency: Advanced mastery of Figma for wireframing, prototyping, UI design, and collaborative design workflows.

• Responsive Web Design: Expertise in designing intuitive and effective user experiences across various devices and screen sizes.

• Cross-functional Collaboration: Demonstrated ability to partner effectively with Digital Marketing, Creative, Brand, Analytics, and Web Operations teams to achieve shared goals.

• Executive Communication: Strong presentation and storytelling skills, with the ability to communicate complex design concepts, rationale, and outcomes clearly to executive leadership.

• Design Lifecycle Management: Experience in governing the end-to-end design process from discovery through implementation and QA.

Preferred Skills:

• Travel Industry Experience: Prior experience within the travel, tourism, or hospitality sectors, understanding the nuances of travel booking journeys.

• eCommerce Expertise: Familiarity with eCommerce best practices, conversion rate optimization (CRO) strategies, and online sales funnels.

• Data Analysis & Insights: Ability to interpret analytics data (e.g., Google Analytics, Adobe Analytics) and user behavior metrics to inform design decisions.

• SEO Best Practices: Understanding of how UX and web design choices impact search engine optimization (SEO).

• Agile/Scrum Methodologies: Experience working within Agile development environments.

📝 Enhancement Note: The experience requirement of "7-10+ years" with "5+ years leading teams" clearly indicates a senior leadership role. The emphasis on Figma, design systems, accessibility for a specific demographic, and driving measurable outcomes like conversion and reduced abandonment positions this as a critical GTM operations role, even though it's within a design function.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase at least 2-3 end-to-end UX/UI design projects, preferably in complex, content-rich web environments or the travel/eCommerce sector.

• Each project should clearly articulate the problem statement, your role and responsibilities, the design process followed (research, ideation, prototyping, testing), key design decisions, and the final outcomes.

• Highlight specific examples of how your design work directly contributed to measurable business objectives, such as increased conversion rates, improved user engagement, reduced abandonment, or enhanced brand perception.

• Include examples of your experience with design systems, demonstrating your ability to create and maintain scalable, consistent design components and guidelines.

Process Documentation:

• Projects should demonstrate a clear understanding of user-centered design methodologies, including user research, persona development, journey mapping, and information architecture.

• Evidence of implementing and iterating on designs based on usability testing, A/B testing, and analytics data is crucial.

• Examples of how you have established or contributed to design standards, style guides, or design system documentation will be highly valued.

• Documentation of how you managed the design lifecycle from concept to launch, including collaboration with development and QA teams, is expected.

📝 Enhancement Note: For a Director-level role, the portfolio needs to demonstrate not just design skills but also strategic thinking, leadership capability, and a results-oriented approach. The emphasis on "measurable business objectives" and "conversion rates" is critical for demonstrating GTM operational impact.

💵 Compensation & Benefits

Salary Range: The base salary range for this role in Boston, MA, is estimated to be $150,000 – $190,000 annually. This range is based on the provided information and industry benchmarks for Director-level UX and Web Design leadership roles in a major metropolitan area with a high cost of living.

Benefits:

• Health & Wellness: Comprehensive and heavily subsidized medical, dental, and vision plans. Access to an on-site gym, holistic wellness sessions, and group fitness classes to support employee well-being.

• Time Off & Leave: Substantial Paid Time Off (PTO), 11 paid holidays (including federal holidays and Juneteenth), and Summer Fridays. Extensive parental leave policy offering 12-16 weeks of paid leave at 100% of base salary.

• Travel Perks: Significant discounts on company trips (50% off for employee and companion, 25% for immediate family), plus exclusive quarterly associate travel deals.

• Financial Security: 401(k) retirement plan with a company match, life insurance, and disability coverage to secure employees' futures.

• Professional Development: Tuition assistance for both professional and personal development, opportunities for overseas travel for professional growth, and direct access to leadership development programs.

• Additional Perks: Commuter benefits, Flexible Spending Account (FSA) options, pet insurance, home and auto discounts, and paid volunteer time off to encourage community engagement.

Working Hours: The role is listed as Full-Time, which typically implies around 38-40 hours per week. The description mentions a "Hybrid/Remote" work arrangement, suggesting flexibility in work location, but specific in-office days might be required.

📝 Enhancement Note: The provided salary range is specific to Boston, MA. Salary expectations can vary significantly based on geographic location and the candidate's specific experience and qualifications. The benefits package is extensive and highly attractive, particularly the travel discounts and generous parental leave, which are unique selling points for Grand Circle Corporation.

🎯 Team & Company Context

🏢 Company Culture

Industry: Travel & Tourism, specifically focused on international adventure travel and cruises for Americans aged 50+. This industry requires a deep understanding of customer motivations, trust-building, and delivering exceptional experiences.

Company Size: Grand Circle Corporation is a significant player in its niche, with "more than 45 offices globally" and "more than two million Americans" having traveled with them. This suggests a large, established organization with a complex operational structure and a global footprint.

Founded: While the founding date isn't explicitly provided, the company's scale and history imply decades of operation, suggesting a mature corporate culture with established processes and a strong brand legacy.

Team Structure:

• The Director of UX & Web Design reports to the EVP, Digital Customer Experience, indicating a high-level position within the digital division.

• The role directly leads a team of UX, UI, and Web Designers, responsible for their growth, performance, and output.

Methodology:

• Data-Driven Design: The role emphasizes "evidence-based design practices," including A/B testing, usability testing, and session reviews, indicating a commitment to data-informed decision-making.

• User-Centricity: A core focus is on "traveler needs" and ensuring "intuitive experiences," pointing to a strong user-centered design philosophy.

• Operational Excellence: The need to "govern the full design lifecycle" and "evolve the Figma-based design system" suggests a drive for process efficiency and operational rigor within the design function.

• Scalable Growth: The strategy and roadmap are geared towards supporting "scalable growth" across brands.

Company Website: grandcircle.com (implied by domain_derived: gct.com, and company description).

📝 Enhancement Note: The company's specialization in travel for an older demographic suggests a need for UX/UI designs that prioritize clarity, ease of use, and trust-building, which are critical operational considerations for customer acquisition and retention in this segment. The global presence implies complex user needs and potential localization challenges that a well-structured UX team would address.

📈 Career & Growth Analysis

Operations Career Level: This is a Director-level position, signifying a significant leadership role within the digital customer experience function. It requires strategic vision, team management expertise, and the ability to drive substantial business impact through design. The scope includes defining strategy, managing a team, and influencing executive-level decisions.

Reporting Structure: The Director reports directly to the EVP, Digital Customer Experience, placing them at a senior level within the digital organization. This provides high visibility and direct access to executive leadership, crucial for driving change and securing resources for design initiatives. The role also requires significant collaboration with various cross-functional departments, indicating a matrixed operational environment.

Operations Impact: The role's primary objective is to enhance the digital customer journey from discovery to booking, directly impacting key GTM metrics such as conversion rates, customer acquisition, and retention. By ensuring a seamless, trustworthy, and engaging web experience, the Director of UX & Web Design plays a critical role in driving revenue growth and customer loyalty for both O.A.T. and G.C.T. brands.

Growth Opportunities:

• Leadership Expansion: Potential to grow into a VP-level role overseeing broader digital experience functions or expanding the scope of the UX/UI team.

• Strategic Influence: Opportunity to shape the future of digital customer experience for a well-established travel company, influencing product roadmaps and business strategy.

• Skill Specialization: Deepen expertise in specific areas like travel UX, accessibility for older demographics, or advanced design system management.

• Cross-Functional Leadership: Gain experience leading large-scale digital transformation initiatives through close collaboration with marketing, product, and technology teams.

• Global Exposure: Opportunity to understand and design for diverse user needs across different international markets, given the company's global operations.

📝 Enhancement Note: The Director-level title and reporting structure suggest significant career growth potential, especially within a company focused on digital transformation and customer experience. The emphasis on driving measurable outcomes aligns with typical career progression in operations-focused roles where impact is quantifiable.

🌐 Work Environment

Office Type: The role is described as "Hybrid/Remote," indicating a flexible work model. This suggests that while there is a physical office presence in Boston, MA, employees have the option to work remotely for a portion of the week, balancing in-office collaboration with remote flexibility.

Office Location(s): The primary office location is Boston, MA (02210). The company has a global presence with over 45 offices worldwide, which may influence team collaboration dynamics and potential for global project involvement.

Workspace Context:

• Collaborative Environment: The hybrid model likely fosters a collaborative environment where in-office days are used for team meetings, brainstorming sessions, and strategic planning, while remote days allow for focused work and individual contribution.

• Digital Tooling: Expect a robust digital toolset, including Figma for design, project management software (e.g., Jira, Asana), communication platforms (e.g., Slack, Teams), and potentially specialized UX research and analytics tools.

• Cross-functional Interaction: The role necessitates frequent interaction with various teams (Digital, Creative, Brand, Analytics, Web Operations), creating opportunities to build relationships and understand diverse perspectives across the organization.

Work Schedule: As a full-time role, standard working hours (approximately 38-40 per week) are expected. The hybrid arrangement offers flexibility, allowing individuals to manage their schedules effectively to balance project deadlines, team collaboration needs, and personal commitments.

📝 Enhancement Note: The hybrid/remote flexibility is a key aspect of the work environment. For operations roles, this often means a focus on asynchronous communication and clear documentation, alongside structured in-person collaboration for strategic alignment and team building.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will likely conduct an initial phone screen to assess basic qualifications, experience, and cultural fit.

• Portfolio Review & Presentation: Candidates will be asked to present their portfolio, focusing on key UX/UI projects. This is a critical step to evaluate design thinking, problem-solving abilities, and communication skills. Be prepared to walk through your process, rationale, and the impact of your work.

• Hiring Manager Interview: A deeper dive into experience, leadership style, strategic thinking, and operational approach with the direct reporting manager or a senior leader in the digital experience team.

• Cross-functional Interviews: Interviews with key stakeholders from teams like Digital Marketing, Creative, Analytics, and Web Operations to assess collaboration capabilities and understanding of their respective domains.

• Executive Interview: Potentially a final interview with the EVP, Digital Customer Experience, to assess strategic alignment and leadership potential.

Portfolio Review Tips:

• Focus on Impact: Clearly articulate the business problem your design solved and the quantifiable results achieved (e.g., % increase in conversion, % decrease in abandonment). Use metrics and data wherever possible.

• Showcase Process: Detail your design process, including user research, ideation, prototyping, testing, and iteration. Explain why you made certain decisions.

• Highlight Leadership: For this Director role, demonstrate your ability to lead a team, mentor designers, and establish design standards and processes.

• Figma & Design Systems: Be ready to discuss your experience with Figma and how you've built or managed design systems, emphasizing consistency and scalability.

• Tailor to Grand Circle: Research Grand Circle Corporation's brands (O.A.T., G.C.T.), target audience (50+ travelers), and current web presence. Frame your portfolio examples to show how your skills align with their specific needs and challenges.

Challenge Preparation:

• Be prepared for a design challenge or case study that may involve optimizing a specific user flow (e.g., trip discovery, booking process) or addressing an accessibility concern for the target demographic.

• Practice articulating your design rationale clearly and concisely, anticipating questions about tradeoffs, potential risks, and how you would measure success.

• Prepare to discuss how you would collaborate with various teams (marketing, analytics, development) to implement your design solutions.

📝 Enhancement Note: The interview process for a Director-level role is rigorous and multi-faceted, aiming to assess not only design acumen but also strategic thinking, leadership capabilities, and operational execution. A strong portfolio that clearly demonstrates measurable business impact is paramount.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The primary tool for UI design, prototyping, and design system management. Mastery is essential.

• UX Research Tools: Proficiency with tools for usability testing, user interviews, persona creation, and journey mapping (e.g., UserTesting.com, Lookback, Maze, Hotjar for session recordings/heatmaps).

• Prototyping Tools: Beyond Figma, familiarity with other prototyping tools might be beneficial for different fidelity needs.

• Design System Management Platforms: Tools or methodologies for organizing, versioning, and distributing design system components.

Analytics & Reporting:

• Web Analytics: Experience with platforms like Google Analytics or Adobe Analytics to track user behavior, conversion funnels, and campaign performance.

• Data Visualization Tools: Familiarity with tools to create dashboards and reports (e.g., Tableau, Power BI, Looker Studio) for presenting design impact to stakeholders.

• A/B Testing Platforms: Experience with tools like Optimizely, VWO, or Google Optimize for conducting controlled experiments on web designs.

CRM & Automation:

• CRM Systems (e.g., Salesforce): While not a direct CRM role, understanding how UX/UI design impacts customer data capture and CRM integration is valuable.

• Marketing Automation Platforms (e.g., HubSpot, Marketo): Awareness of how digital experiences integrate with marketing automation for lead nurturing and customer journeys.

• Project Management Tools: Proficiency in tools like Jira, Asana, Trello, or Monday.com for managing design workflows, sprints, and team tasks.

📝 Enhancement Note: The explicit mention of Figma is critical. The role implies a need for strong analytical capabilities to drive "evidence-based design," so familiarity with analytics and A/B testing platforms is key for demonstrating operational impact.

👥 Team Culture & Values

Operations Values:

• Customer Centricity: A deep commitment to understanding and serving the needs of the 50+ traveler demographic, ensuring all digital interactions are intuitive, accessible, and valuable.

• Data-Driven Decision Making: A strong emphasis on using data from user research, A/B testing, and analytics to inform design choices and measure success, fostering a culture of continuous improvement and accountability.

• Collaboration & Communication: A value placed on open communication and strong partnerships with cross-functional teams (Marketing, Creative, Analytics, Web Ops) to ensure alignment and achieve shared business objectives.

• Excellence & Innovation: Striving for best-in-class design standards, embracing emerging trends, and continuously seeking ways to enhance the digital customer experience and differentiate the brands.

• Inclusivity & Accessibility: A commitment to designing experiences that are usable and enjoyable by everyone, regardless of age, ability, or technical proficiency.

Collaboration Style:

• Cross-functional Integration: The role requires active collaboration with diverse teams, necessitating a style that bridges design, marketing, technology, and business objectives. This involves translating design principles into terms understandable by non-designers and vice-versa.

• Process-Oriented: A structured approach to design and development, emphasizing clear workflows, feedback loops, and governance to ensure efficiency and quality.

• Feedback-Rich Environment: Encouraging constructive feedback among team members and with stakeholders to refine designs and foster continuous learning.

• Strategic Partnership: Engaging with leadership and peers as a strategic partner, contributing insights and solutions that drive business growth and customer satisfaction.

📝 Enhancement Note: The company's focus on a specific demographic (50+) and its mission-driven approach to travel experiences likely shape its core values. A Director of UX needs to embody these values and translate them into tangible digital experiences.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing User Needs with Business Goals: Effectively integrating the needs of the 50+ traveler audience with the company's objectives for conversion, revenue, and scalability.

• Legacy Systems/Processes: Navigating potential complexities or limitations of existing web infrastructure or established design processes within a large, established organization.

• Global Brand Consistency: Maintaining a unified brand experience across different travel brands (O.A.T., G.C.T.) while catering to potentially diverse user segments or regional nuances.

• Measuring ROI of UX: Quantifying the direct financial impact and return on investment of UX initiatives to secure ongoing support and resources.

• Adapting to Evolving Digital Trends: Keeping pace with rapid changes in web technology, user behavior, and design best practices to ensure the company's digital presence remains competitive.

Learning & Development Opportunities:

• Deep Dive into Travel UX: Gaining specialized knowledge in the unique complexities and user journeys of the travel industry.

• Accessibility Expertise: Becoming a subject matter expert in accessibility for an aging demographic, a niche but increasingly important area.

• Design System Maturity: Leading the evolution and scaling of a comprehensive design system, potentially exploring advanced features and integrations.

• Executive Presence & Strategy: Developing skills in high-level strategic planning, executive communication, and influencing organizational change.

• Global User Insights: Understanding and designing for diverse international user bases through exposure to Grand Circle's global operations.

📝 Enhancement Note: The challenges are typical for a leadership role in a large, established company operating in a dynamic industry. The growth opportunities highlight the potential for specialization and strategic advancement within the organization.

💡 Interview Preparation

Strategy Questions:

• "How would you define and evolve the UX strategy for Grand Circle Corporation's brands, considering our specific target audience and business objectives?" (Focus on your strategic framework, research methods, and alignment with GTM goals.)

• "Describe your experience in building and governing design systems. What are the key components, and how do you ensure their adoption and maintenance across teams?" (Highlight Figma experience, process for governance, and impact on efficiency.)

• "How do you balance user needs with business requirements, particularly when dealing with conversion-focused funnels like trip discovery and booking?" (Discuss your approach to user research, A/B testing, and stakeholder negotiation.)

Company & Culture Questions:

• "What attracts you to Grand Circle Corporation and our mission to provide international travel experiences?" (Research the company's values, brands, and mission. Connect your passion for design with their purpose.)

• "How do you foster an inclusive and accessible design culture within your team and across the organization?" (Discuss your experience with WCAG, inclusive design practices, and team training.)

• "Describe your leadership style and how you mentor and develop designers." (Provide specific examples of your management approach and impact on team growth.)

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly define the problem, your role, the process, the solution, and the results. Use a consistent, logical flow.

• Quantify Impact: Emphasize metrics and data. Show how your design decisions led to measurable improvements in conversion, engagement, or reduced abandonment.

• Showcase Figma & Design Systems: Demonstrate your proficiency with Figma and your experience in creating/managing design systems. Highlight the benefits of these systems (e.g., consistency, efficiency).

• Tailor to the Role: Select projects that best illustrate your experience with complex, content-rich websites, travel/eCommerce, and your ability to drive business outcomes.

• Be Prepared for Q&A: Anticipate questions about your design rationale, tradeoffs, future iterations, and how you handle challenges.

📝 Enhancement Note: Preparing specific case studies that highlight your ability to drive measurable GTM outcomes (conversion, funnel optimization) and your experience with design systems and Figma will be crucial for this interview process.

📌 Application Steps

To apply for this operations-focused UX/Web Design leadership position:

• Submit your application through the provided link on the Grand Circle Corporation careers portal.

• Portfolio Customization: Ensure your portfolio prominently features projects demonstrating your ability to drive measurable business outcomes (e.g., conversion rate optimization, funnel improvements, abandonment reduction) within complex web environments, ideally in travel or eCommerce. Highlight your Figma expertise and experience with design systems.

• Resume Optimization: Tailor your resume to emphasize leadership experience (5+ years leading design teams), strategic UX planning, and quantifiable achievements. Use keywords such as "UX Strategy," "Web Design," "Conversion Rate Optimization," "Figma," "Design Systems," "Accessibility," and "Team Leadership."

• Interview Preparation: Practice articulating your design process, rationale, and impact using the STAR method (Situation, Task, Action, Result) for behavioral questions. Prepare to present your portfolio with a focus on business impact and leadership capabilities. Research Grand Circle Corporation's brands and target audience thoroughly.

• Company Research: Understand Grand Circle Corporation's mission, its brands (O.A.T., G.C.T.), and its customer base (Americans aged 50+). Familiarize yourself with their current digital presence and identify potential areas for UX/UI enhancement, demonstrating your strategic thinking and genuine interest.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.