Senior Director, Web

Norwegian Cruise Line Holdings Ltd.•Miami, FL

About The Position

The Senior Director, Web is responsible for enterprise-wide execution and operational excellence for branded, guest-facing web platforms across the full guest journey. The role leads the build functions of Product Management, UI/UX Design, Experimentation, Front-End Engineering, and Web Platform Technology for acquisition and awareness, vacation booking, pre-cruise, post-cruise, and account management experiences across NCLH brands. The position translates stakeholder-defined product priorities into scalable, reliable, high-performing web solutions through disciplined software development lifecycle (SDLC) execution. It oversees budgets, planning, stakeholder alignment, and delivery of projects, enhancements, experiments, and maintenance, using a hybrid model of internal teams and managed service provider (MSP) partners. The role is accountable for delivery excellence, technical integrity, platform performance, release predictability, and operational stability, and drives innovation, scalability, performance optimization, measurable business value, AI adoption, and future AI product integration. It consults on and understands website product strategy but does not own product strategy, prioritization, or commercial performance metrics; it owns how web solutions are delivered, not what is prioritized. The Senior Director leads multidisciplinary teams and works with stakeholders across brands, marketing, operations, revenue management, and technology. The position may require travel and includes other job-related duties as assigned.

Requirements

Bachelor’s degree in Computer Science, Engineering, Information Systems, Business Administration, Digital Media, or a related field.
At least 10 years of progressive experience in technical product management, web application development, AI/LLM, and/or technology leadership.
At least 6 years of senior leadership experience managing managers and cross-functional digital teams.
Experience leading enterprise-scale applications supporting large user bases across multiple brands or business units.
Experience managing hybrid delivery models with internal teams and external vendors/MSPs.
Experience overseeing budgets, financial forecasting, and vendor contracts.
Experience integrating applications with complex enterprise systems and APIs.
Experience leading experimentation frameworks, personalization platforms, and digital optimization initiatives.
Strong enterprise leadership and executive presence, with ability to drive operational excellence across complex digital portfolios.
Deep understanding of Agile delivery models, SDLC governance, and release management.
Strong financial acumen, including budget oversight, forecasting, and portfolio investment management.
Solid technical fluency across enterprise web platforms, integrations, cloud environments, and performance standards.
Data-driven mindset and familiarity with experimentation and optimization frameworks.
Understanding of AI/LLM capabilities and their application within digital platforms.
Strong organizational leadership, talent development, succession planning, communication, and stakeholder alignment skills.

Nice To Haves

Master’s degree preferred.
Experience implementing or scaling AI-driven capabilities within digital products.
Experience in hospitality, travel, cruise, gaming, or consumer-facing digital ecosystems.
Experience supporting distributed or high-availability ecommerce platforms.
Relevant certifications in product management, Agile methodologies, digital strategy, AI/ML, cloud technologies, SEO/AEO, accessibility, or web performance optimization; preferred but not required.

Responsibilities

Partner with stakeholders to translate web product strategies and priorities into executable delivery roadmaps, providing input on feasibility, sequencing, capacity planning, and dependencies.
Lead multidisciplinary teams spanning Technical Product Management, UX/UI Design, Front-End Engineering, CMS Engineering, PIM Engineering, Release Management, Technical SEO, and Experimentation/Research.
Oversee delivery of web initiatives, including large-scale projects, re-platforming, feature enhancements, personalization, experimentation, and production maintenance.
Own and continuously improve the end-to-end web SDLC, including intake, estimation, increment and sprint execution, release management, performance testing, and post-release support.
Ensure predictable, transparent, and measurable delivery across internal and MSP teams.
Partner with stakeholders on the full web guest journey, from acquisition through post-cruise engagement.
Lead experimentation and A/B/x testing to optimize conversion, booking funnel performance, engagement, and usability; ensure experimentation frameworks are scalable, maintained, and reliably executed.
Collaborate with stakeholders to establish and report on KPIs and metrics for revenue/conversion, booking flow optimization, engagement, operational efficiency, and guest satisfaction.
Ensure web platforms meet enterprise standards for scalability, availability, performance, accessibility (WCAG), SEO/AEO/GEO, security, and compliance.
Partner with Core Services/Back-End teams and enterprise systems, including reservation systems, CRM, loyalty, and CDP, to ensure seamless integrations and data continuity.
Oversee CMS/PIM platforms, personalization frameworks, experimentation platforms, and web analytics infrastructure; ensure adherence to enterprise release pipelines.
Manage operating and capital budgets, resource allocation, capacity planning, and financial forecasting for the web portfolio.
Collaborate with the Tech Strategy Team on vendor selection, SaaS platforms, and managed service contracts.
Direct a mixed delivery model of internal FTE pods and MSP/vendor pods.
Report on delivery metrics, including release predictability, cycle time, defect rates, platform uptime, site performance, SEO/AEO health, and technical debt reduction.
Provide executive reporting on roadmap execution, risks, dependencies, and capacity trade-offs.
Own AI strategy within web teams, using AI tools to improve productivity, automate workflows, and enhance operational efficiency.
Enable AI-driven capabilities in web experiences, including personalization, search optimization, content generation, guest assistance, and agentic integration.
Drive adoption of automation and AI-assisted practices across disciplines.
Act as liaison to brand, marketing, operations, revenue management, and technology stakeholders; champion innovation, collaboration, transparency, and passion.
Build and develop a high-performing web organization, including succession planning, leadership development, and operating model clarity across internal and MSP resources.
Perform other job-related duties as assigned.