Managing Director, Data & AI

Job Purpose
The Managing Director, Data and AI is a visionary and grounded leader responsible for forging Liliʻuokalani Trust’s (LT’s) data and artificial intelligence (AI) strategies. This leader will set a bold vision rooted in innovation, cultural understanding, and ethical AI—transforming how we gather insights, make decisions, do our work, and deepen our impact across the state for our beneficiaries (kamaliʻi). The Managing Director will guide LT’s 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
Strategic Leadership & Vision
• Develop and drive a forward-looking data, analytics, and AI strategy that aligns with LT's 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.
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, and storytelling and that support real-time decision-making and cross-team collaboration.
• Foster experimentation and measurement, empowering teams to integrate closely monitored AI/ML capabilities effectively and with confidence.
• Lead efforts to create data products that transform raw data into actionable insights for teams across LT.
• Lerverage AI technologies to enhance data analysis, reduce manual work, and improve workflows and work product quality.
• Partner with stakeholders to ensure the data and AI solutions are designed with scalability, security, robustness, efficiency, and quality in mind.
Collaboration & Change Champion
• Collaborate with the IT delivery and software teams to foster partnerships to deliver data and AI solutions that solve problems for the organization and the kamali’i we serve.
• Act as the subject-matter expert on AI/ML platforms, providing guidance and support to teams on how to leverage these technologies effectively.
• Engage with executive stakeholders, explain complex topics clearly, and build buy-in for long-term data, analytics, and AI investments.
• Champion responsible AI practices, ensuring governance, risk mitigation, an ethical use of AI are embedded in every initiative.
• Establish a cross-functional Data & AI Governance Committee to improve data quality, consistency, and accountability in addition to ensuring the responsible use of AI.
Continuous Improvement and Innovation
• Track performance, data product/solution success, and data model accuracy, using metrics to drive continuous improvement.
• Implement feedback loops to refine data and AI models and ensure they meet or exceed business expectations.
• Build out a data quality framework to ensure model accuracy over time.
• Promote a culture of experimentation, testing new ideas and approaches to continuously improve AI-driven solutions.
Other duties
• Contribute to LT’s success by accepting new assignments, helping team members, learning new skills, and striving to improve team and organization results.
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 in with supervision of collaborative project teams and budget development is desirable.
• Education: Bachelor’s degree in computer science, data science, statistics, mathematics, engineering, information systems, or related technical field required; Master’s 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. Plus, a solid understanding of advanced analytics and modeling concepts with a strong grasp of AI/ML and their practical applications to solve complex business problems and generate actionable insights. Practical experience in developing and deploying solutions in a Cloud environment (e.g., AWS, Azure, Databricks, Snowflake, Tableau). Track record of working with large, complex data sets and disparate data sources across various platforms. Fluency in at least one scripting languages (e.g., R, Python) and SQL preferred.
• Data/AI Strategy and Management: Demonstrated 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: Skilled at translating complex data into accessible, actionable insights for community and executive audiences. Demonstrated ability to facilitate discussions, increase clarity for business decisions, and promote action towards clear, improved outcomes.
• Cultural Competency: Knowledge of or strong commitment to Hawaiian culture, values, and the history of Native Hawaiian youth preferred. Experience working with Indigenous, marginalized, or trauma-impacted communities is a strong asset.

Job Competencies
• Ability to navigate ambiguity and bring clarity to stakeholders to chart a way forward.
• Strategic and systems thinking, critical thinking skills, and creative problem-solving.
• Intermediate to advanced data science skills and knowledge to include but not limited to data wrangling, data analysis, machine learning, data visualization, and statistical analysis.
• Strong oral, written, and visual communication skills to effectively communicate data and insights to a wide range of audiences and to foster adoption of data-informed decision making across the organization.
• Project management skills (intermediate to advanced).
• Ability to effectively conduct multiple projects simultaneously with limited supervision, managing them to timely completion; ability to identify priorities aligned with organizational needs when faced with resource challenges.
• Commitment to staying updated with changes in the field.

Organization Competencies
• Alignment with Queen’s legacy: Understanding and appreciation of Queen Liliuokalani’s story, her legacy and the Hawaiian Culture is foundational to staff’s commitment to working with our Hawaiian children, families and communities. Demonstrates respect for and appreciation of Hawaiian values history, and culture, understanding its implication in one’s work, in fostering meaningful relationships, and in embracing the community served.
• Ho`omau i ka `imi Na`auao (Continuous Learning and Improvement): Committed to creating and reinforcing an environment of continuous learning and improvement.
• Ho`ike i na Mana`o Pono (Effective Communication): Communicates with those we serve and each other in a consistent manner that results in mutual understanding, harmony, and action.
• No'ono'o loi (Critical Thinking and Problem Solving): Actively and skillfully understands, conceptualizes, applies, analyzes, synthesizes, and/or evaluates information and develops and supports fact-based analyses and recommendations
• Ho'o kumu a'e or `Imi hakuhia (Innovation): Identifies and integrates creative ideas into new or existing services and promotes effective problem-solving.
• Pilina Ho`ohana a me ka Hana Hilina`i (Building Relationships and Creating Trust): Manages relationships to create optimal opportunities and move the organization forward.
• Alu Like I ka Hana (Teamwork): Works cooperatively and collaboratively with others throughout the organization in alignment with the organization's objectives.
• Ho`onui I ka `Ike (Capacity Building): Encourages personal growth by exhibiting trust and a belief in the capacity of others.

Mental and Physical Demands:
• Perform light physical work, including climbing, stooping, kneeling, crouching, reaching, and lifting weight of up to 25 pounds. Exposed to outdoor climate and diverse terrain.

Terms and Conditions of Employment
As a condition of employment, employee will be subject to LT’s policies and procedures.

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: Liliʻuonamoku Department: Data and AI


Liliʻuokalani 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.