Lead Associate Principal, AI Solutions

The OCC • Chicago, IL

5d • Hybrid

About The Position

This role serves as OCC’s primary interface between the business and its AI transformation agenda. The AI Solutions Lead will embed with assigned business functions to understand workflows, identify AI opportunities, and build roadmaps for implementation. The role will own initiatives from problem definition through adoption, possessing sufficient technical depth to assess feasibility, evaluate vendors, and support citizen-led development.

Requirements

• Deep understanding of financial services or capital markets operations.
• Experience in post-trade, clearing, custody, or comparable financial market infrastructure strongly preferred.
• Track record of operating at the intersection of business strategy and technical delivery.
• Experience identifying technology opportunities inside a business proactively.
• Working knowledge of modern AI architectures, including retrieval-augmented generation, agent frameworks, and large language model evaluation.
• Demonstrated ability to drive post-launch technology adoption, accountable through genuine usage.
• Familiarity with model risk governance expectations and their implications for AI use in a regulated financial environment.
• AI architecture assessment: retrieval-augmented generation, agent frameworks, and large language model evaluation.
• Requirements specification for AI systems and use case feasibility analysis.
• Vendor and tool evaluation methodology for AI platforms in regulated environments.
• Data analysis and familiarity with data pipeline concepts relevant to AI use cases.
• Process analysis and workflow mapping to support use case scoping and AI readiness work.
• Analytics and BI tools (e.g., Power BI, Tableau) and collaboration platforms (e.g., Jira, Notion).
• 7 or more years of experience in financial services technology or strategy.
• At least five years in post-trade or capital markets infrastructure.
• Domain knowledge in at least one of the following: tokenization and digital asset infrastructure, collateral management and margining, or extended-hours clearing and settlement operations.

Nice To Haves

• Relevant AI product management, project management, or domain certification is a plus.

Responsibilities

• Embed with assigned business functions to develop a grounded understanding of how workflows operate, where decisions are made, and where AI can create meaningful change.
• Identify AI opportunities that redesign work processes rather than simply automating existing ones, distinguishing between incremental improvements and operating model changes.
• Build and maintain the AI transformation roadmap for assigned functions, sequencing initiatives by impact, feasibility, and readiness.
• Partner with functional leaders to define AI-native operations and the steps required to achieve them.
• Own the full lifecycle of assigned use cases: problem definition, stakeholder requirements, scoping, acceptance criteria, delivery oversight, and post-launch adoption.
• Translate business problems into technically grounded requirements for the CTO’s engineering team.
• Own the primary relationship between the business unit and the CTO’s engineering team for assigned initiatives.
• Define the definition of done for solutions, ensuring they solve the intended problem.
• Design and execute adoption plans for assigned use cases, tracking usage and driving resolution of friction points.
• Communicate roadmap, performance, and trade-offs to business stakeholders and leadership.
• Escalate enterprise-level adoption patterns and systemic barriers to the AI Enablement & Change Lead.
• Contribute to portfolio reviews with current status, outcome data, and risk flags for assigned use cases.
• Assess the technical feasibility of proposed use cases, including executability, data prerequisites, and path to production.
• Lead vendor and tool evaluations for non-centralized use cases, providing build-vs-buy recommendations.
• Support business units pursuing contained, non-critical AI development or POCs by providing technical guidance, scoping, and governance guardrails.
• Support organizational AI capability development across functions, helping teams understand AI tool capabilities and usage.
• Define clear boundaries for citizen-led initiatives.
• Keep assigned use case status, outcomes, and risk flags current for portfolio reporting.
• Maintain strong working relationships with assigned business functions and the CTO’s engineering teams.
• Support a strong risk management and governance environment for all AI initiatives.
• Regularly communicate use case progress and value delivery to the Head of AI Strategy.

Benefits

• A hybrid work environment, up to 2 days per week of remote work
• Tuition Reimbursement to support your continued education
• Student Loan Repayment Assistance
• Technology Stipend allowing you to use the device of your choice to connect to our network while working remotely
• Generous PTO and Parental leave
• 401k Employer Match
• Competitive health benefits including medical, dental and vision
• Discretionary bonus

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed