Overview

Job Purpose: The Managing Director, Data and AI is a visionary and grounded leader responsible for forging Lili\u2019iokalani Trust\u2019s (LT\u2019s) data and artificial intelligence (AI) strategies. This leader will set a bold vision rooted in innovation, cultural understanding, and ethical AI11transforming how we gather insights, make decisions, do our work, and deepen our impact across the state for our beneficiaries (kamali\u02bbli). The Managing Director will guide LT\u2019s long-term enterprise data and analytics strategy, including integration of AI capabilities. This role leads a multi-disciplinary team of technical experts who drive business value by developing and integrating AI solutions into business functions and enterprise applications.

Essential Responsibilities

• Develop and drive a forward-looking data, analytics, and AI strategy that aligns with LT\u2019s mission, organizational values, and long-term outcomes for youth.
• Define and execute a strategic roadmap for AI/ML solutions while staying at the forefront of the latest AI practices.
• Build and mentor a diverse team of technical experts.
• Foster a collaborative, curiosity-driven culture where technology serves people—not the other way around.
• Partner with leadership and product teams to understand business needs and prioritize AI/ML initiatives that drive value for the organization.
• Guide AI and data initiatives through the lens of Native Hawaiian culture and trauma-informed practices.
• Develop and maintain robust safety and quality controls for AI use.

Qualifications

• Proven Leadership: 10+ years of experience in data, AI, or digital transformation, with at least 5 years in a leadership role responsible for delivering data/AI-driven solutions. Experience supervising collaborative project teams and budget development is desirable.
• Education: Bachelor\u2019s degree in computer science, data science, statistics, mathematics, engineering, information systems, or related technical field required; Master\u2019s degree or higher preferred. Certification and/or experience with design thinking, user experience development, and change management preferred.
• Technical Expertise: Strong knowledge of data architecture, engineering, and governance frameworks. Solid understanding of advanced analytics and modeling concepts with a strong grasp of AI/ML and their practical applications. Practical experience in Cloud environments (e.g., AWS, Azure, Databricks, Snowflake, Tableau). Experience working with large, complex data sets and disparate data sources. Fluency in scripting languages (e.g., R, Python) and SQL.
• Data/AI Strategy and Management: Ability to lead enterprise-level data/AI strategy from vision to execution and adoption. Familiarity with data quality frameworks, model monitoring, A/B testing frameworks, and continuous model retraining. Hands-on experience with MLOps practices and tools to support model lifecycle management.
• Communication and Consensus-building: Ability to translate complex data into accessible insights for community and executive audiences; facilitate discussions and drive action toward clear outcomes.
• Cultural Competency: Knowledge of or commitment to Hawaiian culture and values; experience with Indigenous or trauma-impacted communities is a strong asset.
• Additional: Experience with data governance, security, and scalable AI solutions.

Job Responsibilities & Capabilities

• Data and AI Management & Innovation: Lead the design, deployment, and scaling of analytic platforms and AI tools that support predictive insights, service optimization, early intervention, storytelling, real-time decision-making, and cross-team collaboration.
• Foster experimentation and measurement to integrate AI/ML capabilities effectively and with confidence.
• Lead efforts to create data products that transform raw data into actionable insights for LT teams.
• Leverage AI technologies to enhance data analysis, reduce manual work, and improve workflows and work product quality.
• Partner with stakeholders to ensure data and AI solutions are scalable, secure, robust, efficient, and high-quality.

Collaboration & Change Champion

• Collaborate with IT delivery and software teams to deliver data and AI solutions that solve problems for LT and kamali\u02bbli served.
• Act as the subject-matter expert on AI/ML platforms, guiding teams on leveraging these technologies.
• Engage with executive stakeholders to explain complex topics clearly and build buy-in for long-term investments.
• Champion responsible AI practices, embedding governance, risk mitigation, and ethical use in every initiative.
• Establish a cross-functional Data & AI Governance Committee to improve data quality, consistency, and accountability, including responsible AI practices.

Continuous Improvement and Innovation

• Track performance and data product/solution success using metrics to drive improvement.
• Implement feedback loops to refine data and AI models to meet business expectations.
• Build a data quality framework to ensure model accuracy over time.
• Promote a culture of experimentation and testing of new ideas to continuously improve AI-driven solutions.

Other Duties

• Contribute to LT\u2019s success by accepting new assignments, helping team members, learning new skills, and improving team and organization results.

Organization & Culture

• Alignment with Queen\u2019s legacy and Hawaiian culture; commitment to working with Hawaiian children, families, and communities.
• Continuous Learning and Improvement; Effective Communication; Critical Thinking and Problem Solving; Innovation; Building Relationships and Trust; Teamwork; Capacity Building.

Mental And Physical Demands

• Perform light physical work; occasional climbing, stooping, kneeling, crouching, reaching; lift up to 25 pounds. Exposure to outdoor climate and diverse terrain.

Terms and Conditions of Employment

As a condition of employment, employee will be subject to LT\u2019s policies and procedures.

Job Details

Job Title: Managing Director, Data and AI
Reports to: VP and Chief Operating Officer
FLSA Status: Exempt
Aligned Executive: VP and Chief Operating Officer
Kipuka: Lili\u02bbiuokalani Trust
Department: Data and AI

Lili\u2019iokalani Trust is an Equal Opportunity Employer. We strive to recruit, train, and retain innovative talent from a diverse candidate pool. All employment decisions will be based on merit, competence, performance, and business needs. Applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, sexual orientation, gender identity or expression, religion, ancestry, genetic information, citizenship, marital/civil union status, arrest and court record, domestic or sexual violence victim status, credit history, disability or veteran/military status or other applicable legally protected characteristics.