Manager, AI & Application Development in Chicago, Illinois at Chai Trust Company LLC

POSITION OVERVIEW

We are seeking an experienced and technically hands-on Manager of AI & Application Development to lead our growing AI and application development practice. Reporting directly to the Senior Director of IT, this individual will serve as a working manager—equally comfortable driving strategic direction and getting into the technical weeds. They will take ownership of our AI integration roadmap, manage a team of application developers, and directly oversee an external AI implementation consultant.

This is a high-impact, high-visibility role at a company that is genuinely committed to AI adoption. The right candidate will thrive in an environment where experimentation is encouraged, momentum is building, and the opportunity to shape how AI is used across a sophisticated financial services enterprise is real.

KEY RESPONSIBILITIES

AI Strategy & Integration

• Own and drive the organization’s AI integration roadmap across all four business divisions, in close collaboration with the Senior Director of IT.
• Identify, evaluate, and implement AI-powered solutions that deliver measurable business value—spanning data analysis, communications drafting, budget forecasting, dashboard development, and client-facing portals.
• Serve as the internal subject matter expert on Claude (Anthropic), Microsoft 365 Copilot, and emerging AI tooling.
• Design and implement prompt engineering strategies, RAG pipelines, and AI agent workflows using the Claude API, Copilot Studio, and Power Automate.
• Lead integration efforts connecting AI capabilities to core business systems including Microsoft Business Central, Addepar, Microsoft Fabric, Dataverse, SharePoint, and Microsoft Dynamics.
• Maintain awareness of the AI landscape and proactively surface opportunities relevant to financial services, family office operations, and investment management.

Team Leadership & Management

• Directly manage the Application Development team (currently focused on SharePoint, Microsoft Dynamics, Microsoft Fabric, and Dataverse).
• Foster a collaborative team culture that balances innovation with operational discipline and security-mindedness.
• Identify points of overlap between AI initiatives and existing AppDev workstreams; coordinate cross-functional efforts to avoid duplication and maximize leverage.
• Mentor team members on AI tools, techniques, and best practices as they become increasingly relevant to all application development work.

Project & Delivery Management

• Partner with the VP of Strategic Projects and Operations to evaluate and prioritize incoming project requests, ensuring AI and application development efforts are aligned with cross-divisional business objectives.
• Manage a portfolio of concurrent AI and application development projects, ensuring delivery on time and aligned to business priorities.
• Work closely with division stakeholders—family office, investments, shared services, and international—to translate business needs into technical requirements and AI-driven solutions.
• Establish standards and governance around AI tool usage, prompt libraries, integration patterns, and data handling practices.
• Collaborate with the IT Security function to ensure all AI solutions meet confidentiality, PII handling, fiduciary, and SEC compliance requirements.

QUALIFICATIONS

Required

• Hands-on experience with AI/LLM tools and frameworks, including prompt engineering, retrieval-augmented generation (RAG), and AI agent/workflow design.
• 5+ years of experience in application development, IT management, or a closely related field, with demonstrated progression in scope and responsibility.
• Experience with the Claude API (Anthropic) and/or Microsoft 365 Copilot and Copilot Studio.
• Proficiency with Microsoft Power Platform (Power Automate, Power Apps) and the ability to build integration workflows connecting AI to enterprise systems.
• Experience integrating AI and business applications with systems such as Microsoft Business Central, Microsoft Dynamics, Microsoft Fabric, Dataverse, or comparable ERP/CRM platforms.
• Demonstrated experience managing technical teams and/or contractors, including work planning, performance feedback, and mentorship.
• Strong project management skills with the ability to manage multiple concurrent initiatives across diverse stakeholder groups.
• A strong appreciation for data security, confidentiality, and compliance requirements in a regulated or sensitive environment.

Preferred

• Experience in financial services, family office, investment management, or a similarly regulated or high-confidentiality environment.
• Familiarity with Addepar or comparable portfolio management/reporting platforms.
• Experience with SharePoint Online development, SPFx, or Microsoft 365 administration.
• Familiarity with Microsoft Purview, sensitivity labeling, or enterprise data loss prevention (DLP) practices.
• Understanding of SEC compliance requirements or fiduciary data handling obligations.
• Experience building internal AI assistants, knowledge bases, or AI-powered portals using RAG architectures.