Senior Data Scientist & AI Engineer

ABOUT THE RICHARD L. DUCHOSSOIS FOUNDATION The Richard L. Duchossois Foundation (RLD) was founded in 2022 and launched formal operations in 2024. The Foundation is committed to addressing seemingly intractable social problems with imagination and passion. We strive to improve the lives of families and veterans, and to cultivate entrepreneurs through data driven and collaborative approaches to funding. We seek to practice philanthropy with rigor and from a place of listening and strive to be a learning organization – to always seek greater understanding of our funding priorities. While our home and our priority is the Chicago region, we may consider national efforts that are aligned with our mission, values and goals. ABOUT THE DATA STRATEGY & INSIGHTS TEAM RLD Foundation’s Data Strategy & Insights team provides a backbone for the foundation's commitment to evidence-informed grantmaking and sector-wide learning. We strive to transform data from a compliance exercise into a catalyst for change, building a continuous cycle of inquiry, insight, and action within RLD Foundation, across our grantee partners, and throughout Chicago's social sector ecosystem. RLD Foundation is building a team of data scientists and researchers to advance six interconnected areas of work: - Generating data-driven insights to inform grantmaking strategy - Embedding iterative strategic learning processes into grant portfolio management - Developing monitoring and evaluation systems that measure what matters - Supporting grantee data capacity to help partners unlock the value of their own information - Strengthening ecosystem-wide data infrastructure where possible - Designing and building robust internal and public-facing data systems and tools. Throughout our work, the team champions data principles that are purposeful, community-grounded, and capable of driving lasting, systemic change. We strive to be a learning organization, valuing thoughtful iteration, transparency about what we know and don't know, and learning in close partnership with each other, grantees, and communities. JOB SUMMARY RLD Foundation seeks a mission-driven Senior Data Scientist & AI Engineer to join our Data Strategy & Insights team. In this role, you will play a central part in advancing the foundation’s data strategy in a highly collaborative environment. The position sits at the intersection of data and AI engineering, advanced analytics, and data strategy, offering the opportunity to do technically rigorous, high-impact work in service of social change. The role has two co-equal primary responsibilities: (1) building and owning RLD Foundation’s core data infrastructure and AI-enabled analytics platform, and (2) conducting advanced analytics to generate insights that inform grantmaking strategy and organizational learning. The position will architect the technical systems that enable high-quality data work across the foundation while also serving as a lead analyst who delivers clear, actionable insights to program teams and leadership. There will also be opportunities to contribute to broader data strategy development and selective grantee- and field-facing data capacity building initiatives. You will report to the Director of Data Strategy & Insights and work alongside a Senior Research and Insights Analyst, with the potential for the team to grow as the organization evolves. This is an early-stage data environment with significant opportunity to shape systems, tools, and analytical approaches. You will bring technical leadership to the team, with the autonomy to architect solutions and make strategic technical decisions that will define how the foundation uses data to catalyze meaningful change. We recognize this role asks for an uncommon combination of technical depth and mission commitment. The right candidate brings senior-level data engineering and analytics expertise and is equally energized by applying those skills to advance social good. If you're someone who could thrive in tech but would rather build systems that help families, veterans, and entrepreneurs in Chicago, this role offers that meaningful intersection. KEY RESPONSIBILTIES Data Infrastructure, Systems, and Tools Lead the development and maintenance of modern and scalable data infrastructure to undergird RLD Foundation's data strategy and AI-enabled knowledge platform: • Architect and maintain RLD Foundation’s cloud-based data infrastructure, ensuring performance, scalability, and security • Develop and automate ingestion and transformation pipelines to build an integrated warehouse of data from internal systems (grants management, CRM, program data) and external sources (public APIs, data partners, research institutions, government) • Support the development of analytical tools and web-based platforms that enable staff, board, and ecosystem partners to access real-time insights • Implement rigorous data quality, validation, and governance protocols • Develop data dictionaries, and document all code and data processing workflows Data Analytics & Strategic Insights Collaborate with the Data Team and Program Directors to develop an institutional data practice where we ask powerful questions, collect relevant data, generate insights, and take action: • Apply statistical, machine learning, and geospatial techniques for applied analysis, with advanced NLP and LLM-based methods primarily used within the AI-enabled knowledge platform • Creatively source and curate relevant datasets from public, private, academic, and alternative sources relevant to RLD Foundation’s work and to fill sector data gaps • Conduct exploratory data analysis across RLD Foundation’s internal and partner datasets to identify trends, gaps, and opportunities • Advise on key data points for data briefs and white papers that share insights transparently with grantees and the broader sector AI-Enabled Knowledge Platform Building on RLD Foundation's core data infrastructure outlined above, this role will: • Lead the design and development of an AI-enabled knowledge layer, in collaboration with external partners as appropriate, that integrates structured data (grants, finances, open data, acquired private data) and unstructured data (reports, research, meeting notes, transcripts), into a unified, query-able system • Build retrieval-augmented generation (RAG) pipelines that allow staff to ask complex strategy questions and receive synthesized, source-grounded answers (i.e. “What strategies have been most effective in creating family-sized affordable housing in Chicago, and where do gaps remain?”) • Implement metadata, embeddings, and document indexing to support semantic search, cross-dataset linking, and transparent sourcing • Partner with program teams to translate learning and strategy questions into AI-supported workflows and analytical products • Ensure responsible AI practices, including data governance, bias awareness, privacy protection, and explainability of outputs Data Strategy • Partner with the Director of Data Strategy & Insights, Program Directors, Grants Manager, and Research Analysts to identify datasets to acquire and analyses to conduct that support strategic learning, monitoring, and evaluation priorities • Contribute to the design and tracking of indicators and metrics that can help RLD Foundation better understand baselines, progress and trends in its focus issue areas • Collaborate across the organization to ensure all data collection systems and tools are thoughtfully designed to capture information that aligns with organizational needs and learning questions • Contribute to a culture of iterative learning around data use Grantee & Field Capacity Building Contribute to RLD Foundation's grantee-centered approach to data capacity building, supporting nonprofits use data to strengthen their own work. This work will be selective and episodic, not a primary day-to-day responsibility: • Work with select grantees to understand their data aspirations, current pain points, and where RLD Foundation support could help them build data capacity • Partner with grantees and capacity-building vendors to shape and support data initiatives; provide hands-on support selectively when it creates high leverage for learning or infrastructure\ • Contribute analysis and expertise to collaborative initiatives that enable grantees, peer funders, and others to learn together from data • Create public-facing data tools and resources for grantees and the broader field