Vice President, Commercial Systems Strategy and AI Innovation

Job Description

Holland America Line has been exploring the world since 1873. Our ships offer innovative features and enriching experiences focused on destination exploration and personalized travel, inviting guests to savor the journey.

We’re looking for an experienced Vice President, Commercial Systems Strategy & AI Innovation to fill this role. The Vice President of Commercial Systems Strategy and AI Innovation is a senior executive role reporting to the Chief Revenue Officer, responsible for shaping the future of commercial operations across multiple cruise brands. This position combines strategic leadership, technology innovation, and operational excellence to deliver measurable business impact.

The VP will lead enterprise-wide initiatives to optimize the POLAR reservation system, define and execute product strategy, and pioneer agentic AI solutions that transform customer engagement, analytics, and crew planning. With direct oversight of a $20M+ annual budget and influence on $8B in net ticket revenue, this role manages a team of 30+ professionals across three functional areas—POLAR Operations, Product Strategy, and AI Innovation.

The VP will drive cross-brand alignment, ensuring system enhancements and AI initiatives support both enterprise objectives and unique brand requirements. Key responsibilities include leading large-scale technology programs, developing multi-year product roadmaps, and implementing AI-driven capabilities that improve efficiency, reduce costs, and unlock new revenue opportunities. Success in this role requires exceptional strategic vision, deep expertise in data science and AI technologies, and the ability to communicate complex concepts to C‑suite executives and external partners.

The VP will serve as a trusted advisor to senior leadership, champion innovation, and foster a culture of continuous improvement. This position has transformational impact on the organization, setting the standard for commercial systems and AI innovation while driving long‑term growth and operational agility.

Here’s a summary of what Holland America Line is looking for in its Vice President, Commercial Systems Strategy & AI Innovation. Is this you?

• Oversight of the POLAR system remains top priority across all five brands.
• Direct a team of super users providing system support to commercial and operations departments, travel agency partners, and vendors impacting all brands.
• Craft and execute data science strategies that leverage AI/ML capabilities.
• Lead strategic, transformational projects including creating and leading RFPs, securing resources, creating and maintaining budgets (+$20M annually), ensuring project objectives are met through solid internal and external communication, and delivering projects on time within budget.
• Ensure all User Acceptance Testing (UAT) results are documented and support multiple revenue and finance controls to ensure compliance.
• Drive yield uplift through POLAR optimization and AI‑enhanced pricing strategies.
• Oversee technical development and maintenance of POLAR and integrated systems.
• Provide the technology, tools, and data to enable the delivery of $8B in annual net ticket revenue.
• Build and maintain the Strategic Operations financial forecast.
• Lead cross-brand alignment to optimize the POLAR reservation system.
• Drive the enterprise‑wide POLAR reservation system strategy by facilitating collaboration across all five brands’ commercial teams.
• Lead the cross‑brand prioritization process to ensure alignment on system enhancements and resource allocation.
• Monitor system performance and make data‑driven decisions to improve efficiency and effectiveness.

• Lead the Product Strategy team responsible for gathering, prioritizing, and translating business requirements from all five brands into actionable system enhancements.
• Direct a team of 2 Product Managers who serve as the voice of the brands, ensuring POLAR meets diverse commercial needs.
• Establish and manage the product roadmap governance process, balancing competing brand priorities with enterprise‑wide strategic objectives.
• Create…