VP, Data & AI

The VP, Data & AI leads AI strategy, adoption, and execution for Hawaii Mobility, supported by scalable enterprise architecture and trusted data. This role partners with operations and technology leaders across Hawaii mobility, Australia mobility, Servco music, and the investment portfolio to guide shared AI and data priorities, influence roadmaps, and identify opportunities for shared capabilities.

KEY OUTCOMES:

Strategy & Business Outcomes

Set a clear AI and data vision for Hawaii mobility that strengthens customer relationships and core operations while opening paths to new services. Partner with Australia mobility, Servco music, and the investment portfolio on shared priorities, respecting each business's decision rights.

Work shoulder to shoulder with operators: listen to the work, co-design useful tools, teach practical skills, and build governed solutions together. Make adoption, workforce capability, and measurable customer and operating results shared outcomes.

Own the Hawaii mobility AI and data investment plan, capital and operating budgets, and business cases. Prioritize by strategy, customer value, financial return, feasibility, and risk; set baselines and accountable owners, pace change to operational readiness, and reallocate capacity as evidence develops.

Production AI & Responsible Delivery

Lead predictive and generative AI, agents, and automation from opportunity through production and workforce adoption. Sponsor reusable MLOps and LLMOps delivery patterns for governed context and tool access, evaluation, testing, release, monitoring, human handoffs, rollback, and incident learning.

Set risk-based governance informed by NIST AI RMF, its Generative AI Profile, and ISO/IEC 42001. Require appropriate permissions, human oversight, traceability, and auditable decisions; hold teams and partners accountable for reliable production operations.

Measure revenue, margin, productivity, cost to serve, customer impact, adoption, and reliability against total investment. Stop, adjust, or scale initiatives based on evidence.

Enterprise Architecture & Trusted Data

Lead enterprise architecture for Hawaii Mobility through the Director, Enterprise Architecture. Guide the Director in tailoring and adopting lean, leading enterprise architecture and AI-first patterns across Servco, grounded in Digital Strategy principles of Omnichannel Integration, Datafication, Tech Modernization, Problem Led delivery, Highly Automated platforms, and Talent Driven capability.

Own the data platform roadmap and economics across Databricks, Azure, and connected systems. Ensure governed, reusable data products, quality, lineage, access, and observability; retain architecture decisions, code, models, and intellectual property in Servco-controlled systems.

People & Cross-Business Partnership

Lead and develop the Director, Enterprise Architecture and Director, Data Visualization, Analytics & Automation and their teams. Attract and grow Servco talent, delegate ownership, transfer knowledge from partners, invite feedback, and celebrate shared wins with operators.

Coordinate agreed shared capabilities and investments with Australia mobility, music, and investments. Build trust through transparent tradeoffs, communicate delivery, capacity, value, and risk to the Executive Committee, and keep accountability with each business leader unless otherwise agreed.

QUALIFICATIONS:

Education:

Bachelor's or Master's in a related field, or equivalent demonstrated experience.

Work Experience:

12+ years across AI, data, architecture, or engineering, including senior leadership of multidisciplinary teams and accountability for strategy, delivery, budgets, and measurable outcomes.

Proven production delivery of predictive or generative AI, agents, and automation at scale, with adoption, reliability, responsible controls, and measurable customer and financial impact.

Experience in vertically integrated manufacturing, distribution, retail, or comparable operations; able to improve the core business while staging innovation at a pace teams can adopt.

Experience with connected customer, vehicle, trade, finance, fulfillment, and service journeys across digital and physical touchpoints; distributed teams across the US and Australia. (Preferred)

Skills:

Depth in enterprise architecture and governed data platforms, ideally Databricks on Azure or a comparable cloud stack, with the judgment to guide pragmatic AI-first patterns and technical leaders.

Ability to connect AI opportunities to investment cases, capital and operating tradeoffs, operating performance, customer outcomes, and realized benefits.

A self-aware leader who listens with humility, earns trust across frontline and executive teams, develops others, communicates decisions transparently, and aligns businesses through influence and shared purpose.

Depth in MLOps and LLMOps, governed retrieval and tool access, agent evaluation, tracing, production monitoring, security, privacy, and unit economics. (Preferred)

About Servco:

At Servco, we’re committed to providing valuable mobility solutions to empower people through the freedom of movement and opportunity. From Australia to California, and of course, Hawaii, Team Servco is a collective of over 2,000 like-minded individuals guided by our four Core Values of Respect, Service, Teamwork, and Innovation. For over 100 years, we have been dedicated to superior service, to both our customers and team members. We look forward to helping you create Life:Moments that matter to you.

Interested?

Visit www.servco.com/careers to apply online or email us at careers@servco.com .

Equal Opportunity Employer and Drug-Free Workplace

Pay Range: $176,900.00 - $268,900.00 per year