Program Manager, AI and Automation

We are seeking a highly capable Program Manager to lead and manage Stewart's expanding portfolio of Artificial Intelligence (AI) and Automation projects and initiatives. This strategic role requires a proven leader who can bring structure, transparency, and momentum to a fast-moving program landscape, ensuring alignment with enterprise priorities, high-quality execution, and measurable outcomes.

This is a hands-on leadership role with visibility at the executive level. The ideal candidate will bring strong program management discipline, excellent stakeholder engagement skills, and the ability to deliver with minimal oversight.

If you are a driven, organized, and strategic program leader who can proactively solve problems, own outcomes, and confidently represent initiatives at the highest levels, we want to hear from you.

Key Responsibilities

• Lead the AI & Automation Program Portfolio Oversee program governance, project delivery, and overall health of initiatives across the organization.
• Drive Portfolio Transparency Develop and maintain dashboards and reporting mechanisms that provide real-time visibility into project status, risks, and performance metrics.
• Collaborate Across Teams Serve as the central point of coordination between business, product, and IT stakeholders, ensuring alignment on priorities, timelines, and deliverables.
• Enforce Governance Standards Ensure adherence to PMO best practices, enterprise frameworks, and change management processes.
• Anticipate and Resolve Issues Identify risks and bottlenecks early, facilitate resolutions, and maintain momentum across projects.
• Support Change and Adoption Partner with change management leads to ensure successful deployment and user adoption of solutions moving into production.
• Represent the Portfolio Communicate program progress and strategic alignment with confidence in executive forums and cross-functional meetings.
• Participate in AI Strategy Engage actively in the enterprise AI Committee and contribute to shaping AI and automation strategy.

Core Competencies

Competency

Description

Strategic Thinking

Ability to align program activities with enterprise goals and prioritize initiatives that drive business value.

Executive Presence

Confidently communicates with senior leadership, influencing decisions and presenting updates with clarity and credibility.

Accountability

Takes full ownership of deliverables and outcomes, following through with minimal direction.

Proactive Problem-Solving

Anticipates roadblocks and applies creative thinking to navigate constraints and resolve issues.

Cross-Functional Leadership

Builds strong working relationships across business, IT, and product teams to drive collaboration and alignment.

Operational Discipline

Applies consistent program management methodologies, reporting frameworks, and governance standards.

Change Agility

Adapts quickly to evolving priorities, emerging technologies, and shifting business needs.

Communication Excellence

Delivers clear, concise, and audience-appropriate communication in both written and verbal formats.

Qualifications

What Success Looks Like