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?

Responsibilities

Execution and Performance

• 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.

Product Strategy and Brand Requirements Leadership

• 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 and maintain a multi‑year product vision for the POLAR ecosystem that supports differentiated brand experiences while maximizing platform efficiency.
• Develop business cases for major product initiatives, quantifying ROI and strategic value.
• Lead quarterly product planning sessions with brand leadership to align on priorities and resource allocation.
• Ensure product requirements are comprehensive, clearly documented, and include success metrics.
• Bridge the gap between brand commercial strategies and technical implementation capabilities.
• Champion user‑centered design principles to enhance system usability and adoption.
• Oversee the product backlog management process, ensuring transparency and data‑driven prioritization.

Agentic AI Innovation and Implementation Leadership

• Build and lead a new AI Innovation team (6 FTEs) focused on deploying agentic AI solutions across Princess, Holland America, and Seabourn.
• Develop and execute a comprehensive AI strategy that drives revenue growth and operational efficiency across multiple business functions.
• Contact Center AI Initiatives:
• Deploy AI agents to handle routine customer inquiries, reducing handle time and improving customer satisfaction.
• Implement intelligent routing and real‑time agent assistance tools.
• Create predictive models for contact volume forecasting and optimal staffing.
• Analytics & BI AI Initiatives:
• Develop agentic AI systems that proactively identify revenue opportunities and market trends.
• Automate report generation and insight delivery to commercial leadership.
• Create self‑service analytics capabilities powered by natural language processing.
• Crew Planning AI Initiatives:
• Implement AI‑driven crew scheduling optimization to reduce costs while improving service quality.
• Develop predictive models for crew demand across ships and itineraries.
• Automate crew assignment processes based on skills, preferences, and operational needs.
• Partner with Data Science, Technology, and brand leadership to ensure AI initiatives deliver measurable business impact.
• Establish AI governance frameworks, including ethical AI principles, data privacy compliance, and model monitoring.
• Build the business cases for AI investments, tracking ROI and continuous improvement.
• Stay abreast of emerging AI technologies and evaluate their potential application to cruise operations.
• Manage relationships with AI vendors, consultants, and technology partners.

Innovation Leadership and Process Improvement

• Identify opportunities for process automation to streamline operations and reduce manual workload across all brands.
• Implement agile methodologies to increase responsiveness and adaptability in commercial operations.
• Collaborate with enterprise technology teams to integrate advanced tools and technologies into the reservation and commercial systems.
• Lead and develop VPs, AVPs, and Directors across three functional teams (POLAR Operations, Product Strategy, AI Innovation), including conducting staff meetings, building team continuity, providing coaching and feedback, monitoring performance, and writing annual evaluations.
• Establish short and long‑term departmental goals and objectives for middle management to execute against while maintaining high standards of performance.
• Champion performance metrics, setting clear KPIs to measure team success and drive continuous improvement.
• Foster a culture of experimentation and calculated risk‑taking to accelerate innovation.
• Create forums for cross‑brand knowledge sharing and best practice dissemination.

Strategic Advisory and Stakeholder Management

• Serve as a trusted advisor to C‑suite leadership and brand presidents, advocating for growth while acknowledging current constraints.
• Provide strategic insights and recommendations to senior leadership on reservation system improvements, product strategy, and AI innovations.
• Balance the need for growth with the practical constraints of existing systems and resources.
• Foster a culture of continuous improvement and innovation across the commercial organization.
• Serve as the trusted advisor to brand POLAR owners and Revenue Management leadership, balancing growth initiatives with operational constraints.
• Ensure business cases for POLAR and AI investments deliver measurable ROI for the Corporation.
• Translate business needs into clear requirements for Technology teams, serving as the bridge between commercial and technical stakeholders.
• Represent the division in enterprise‑wide strategic initiatives and technology governance forums.
• Build and maintain relationships with external consultants, vendors, and industry thought leaders.

Cross‑Functional Project Leadership

• Lead cross‑functional projects from initial concept through delivery, spanning multiple brands and functions.
• Oversee project teams comprising members from various departments and brands, including matrixed resources from Technology, Finance, and Operations.
• Develop project plans, timelines, and budgets, ensuring projects are delivered on time and within scope.
• Conduct regular project reviews and provide updates to executive stakeholders.
• Identify and implement process improvements across product build, promotions, and change management workflows.
• Drive automation initiatives to increase the commercial organization’s speed and agility.
• Lead continuous improvement efforts within Revenue Management Operations across all brands.
• Develop metrics and KPIs to measure operational efficiency gains and business impact.
• Identify opportunities to leverage data science and advanced analytics to enable growth.

Analytics, Performance Management & Financial Stewardship

• Utilize analytics, key performance indicators, and financial metrics to drive quantifiable change.
• Analyze data to identify trends, opportunities, and areas for improvement in the reservation system and AI applications.
• Develop and track key performance indicators (KPIs) to measure the success of system enhancements and AI initiatives.
• Use financial metrics to assess the impact of changes on revenue and costs.
• Ensure adherence to all applicable laws and standard operating procedures as they pertain to the SOX Audit process and Ethics and Compliance.
• Responsible for the quality and integrity of over $20M in POLAR reservation system process and budget, plus AI initiative investments.
• Drive the company’s profitability assessment by making recommendations and implementing initiatives to improve performance.
• Create executive dashboards that provide visibility into system performance, product delivery, and AI ROI.

Compliance & Corporate Governance

• Adheres to Corporate Policies and Procedures, including Code of Business Conduct & Ethics, Audit Procedures, and any control‑related responsibility for financial data entered, stored, or reported via business systems within employee’s control.
• Ensure AI governance, data privacy, and ethical AI practices across all initiatives.
• Maintain SOX compliance for all systems and processes under purview.

Requirements

• POLAR and POLAR system experience strongly preferred.
• Deep understanding of revenue management strategies and pricing optimization.
• Strong understanding of travel industry reservation and booking system applications.
• Experience with commercial systems and enterprise technology architecture.
• Knowledge of AI/ML technologies, including agentic AI, natural language processing, and predictive analytics.
• Understanding of data governance, AI ethics, and privacy regulations.
• Exceptional leadership skills with experience managing diverse teams across multiple disciplines.
• Proven ability to build high‑performing teams and develop talent.
• Experience leading through influence in matrixed organizations.
• Strong change management capabilities, particularly for technology adoption.
• Outstanding strategic thinking and problem‑solving abilities.
• Strong analytical skills and ability to translate data into actionable insights.
• Experience building business cases and demonstrating ROI.
• Ability to structure ambiguous problems and develop innovative solutions.
• Exceptional communication skills with ability to influence C‑suite executives.
• Proven track record of effectively working with external consultants and vendors.
• Ability to translate complex technical concepts for non‑technical audiences.
• Strong stakeholder management skills across multiple brands and functions.
• Ability to manage multiple concurrent strategic initiatives.
• Strong project and program management capabilities.
• Track record of delivering results on time and within budget.
• Experience with agile methodologies and modern product development practices.
• Bachelor’s Degree in Business, Finance, Operations, Data Science, Computer Science, or related field required.
• MBA, MSBA, MS in Data Science, or other relevant Master’s Degree strongly preferred.
• 15+ years of progressive experience in strategy, revenue management, commercial systems, product management, or other analytical and strategic roles.
• 8+ years of experience leading large, cross‑functional teams and complex programs.
• 5+ years of experience with AI/ML technologies, including recent exposure to generative AI and agentic AI systems.
• Proven experience implementing enterprise‑wide systems across multi‑brand organizations.
• Experience in cruise, travel, hospitality, or other complex consumer‑facing industries preferred.
• Track record of delivering measurable ROI through technology and process innovation.
• This is a hybrid position, based in our Seattle office. Candidates must be comfortable coming into the office 3 days/week (currently Tuesday‑Thursday).

What You Can Expect

• Cruise and Travel Privileges for You and Your Family
• Health Benefits
• 401(k)
• Employee Stock Purchase Plan
• Training & Professional Development
• Tuition & Professional Certification Reimbursement
• Base Salary/Hourly Range: $230,000 to $280,000. The range is applicable for the labor market where the role is intended to be hired. Final base salary is directly related to each candidates' qualifications and experience uniquely.

Our Culture…Stronger Together

Our highest responsibility and top priority is compliance, environmental protection and the health, safety and well‑being of our guests, the people in the communities we touch and serve, and our shipboard and shoreside employees. Please visit our site to learn more about our Culture Essentials, Corporate Vision Statement and our Core Values at:

Holland America is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances.

Americans With Disabilities Act (ADA)

Holland America will provide reasonable accommodations with the application process, upon your request, as required to comply with applicable laws. If you have a disability and require assistance in this application process, please contact View email address on click.appcast.io

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