Executive Principal, AI Product & Strategy

The OCC • Chicago, IL

3d • Hybrid

About The Position

We are seeking a senior leader to drive the strategic direction and product management of our enterprise AI and Generative AI portfolio. This is a high-impact, portfolio-level role responsible for treating AI capabilities as products — complete with roadmaps, user experience standards, adoption metrics, and continuous improvement cycles. This role operates at the intersection of technology strategy, product leadership, and AI domain expertise. You will serve as the connective tissue between AI/ML technical teams and business stakeholders, leading through influence rather than direct organizational authority. As the portfolio matures, the role may evolve to include direct reports and people leadership.

Requirements

• 10+ years of progressive experience in product management, technology strategy, or applied AI/ML, with a significant portion in financial services or other highly regulated industries.
• Demonstrated track record of leading enterprise-scale programs or product portfolios through influence rather than direct line authority.
• Experience building business cases for technology investments and presenting to C-suite or senior executive audiences.
• Hands-on familiarity with AI/ML technologies, including generative AI, with the ability to evaluate technical feasibility and translate capabilities into business value.
• Strategic thinking: Ability to set direction for a complex, evolving portfolio and make principled trade-offs across competing priorities.
• Cross-functional influence: Proven ability to drive outcomes across organizational boundaries without relying on org chart authority — through coalition-building, program design, and stakeholder engagement.
• Business translation: Comfort operating fluently between deeply technical AI/ML teams and non-technical business and risk stakeholders.
• Governance mindset: Understanding of responsible AI principles and experience implementing oversight frameworks in regulated environments.
• Measurement orientation: Strong analytical instincts with experience defining and operationalizing success metrics for technology products or platforms.

Nice To Haves

• Experience at a financial institution, exchange, financial market utility, or fintech in a product, strategy, or applied AI role.
• Experience establishing AI/ML governance committees, oversight models, or centers of excellence.
• Background that includes a blend of technical credibility (e.g., ML engineering, data science, platform architecture) and strategic or product leadership.
• Experience scaling programs through partnerships — academic, industry, or cross-organizational.

Responsibilities

• Portfolio Strategy & Ownership: Own the enterprise AI product portfolio end-to-end, setting vision, strategy, and prioritization across multiple AI capabilities and initiatives.
• Identify opportunities to redesign traditional business processes using AI-native approaches, driving transformation that goes beyond incremental automation.
• Develop and maintain product roadmaps that balance near-term business value with long-term strategic positioning.
• Business Case Development & Investment Strategy: Build rigorous analytical foundations for AI investment decisions, including cost-benefit analyses, ROI modeling, and strategic framing.
• Present business cases and portfolio updates to senior leadership, translating technical potential into business language.
• Metrics, Measurement & Optimization: Establish measurement frameworks for AI adoption, effectiveness, and return on investment across the portfolio.
• Define and track KPIs that demonstrate business impact, not just technical performance.
• Drive continuous improvement through data-informed iteration.
• Governance & Responsible AI: Ensure responsible AI practices are embedded into the product lifecycle, including fairness, transparency, explainability, and compliance with our regulatory environment.
• Partner with risk, legal, and compliance functions to maintain governance standards appropriate for a regulated financial services organization.
• Cross-Functional Leadership: Build alignment across technology, business, and risk functions through shared frameworks, standards, and success metrics.
• Influence prioritization and resource allocation through stakeholder relationships and compelling business cases.
• Serve as a trusted advisor to both technical teams and business leaders, bridging the gap between what AI can do and what the organization needs it to do.

Benefits

• A highly collaborative and supportive environment developed to encourage work-life balance and employee wellness.
• 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

What This Job Offers

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