Head Of Program Management Jobs in Ontario (NOW HIRING)

SUMMARY

The Lead, AI Program Management owns the health of Chubb's Global AI program portfolio and the delivery outcomes of one of its highest-priority AI programs.

Reporting to the VP, AI Programs, Strategy & Operations, this role is accountable for staying on top of how every Global AI program is performing, for giving leadership a clear, independent view of status, risk, and value, and for delivery oversight over the Head of Global AI's flagship program. This role owns proactive risk governance and value measurement. They also define how AI programs are governed, delivered, and measured as the Head of Global AI's portfolio scales, and brings AI directly into the practice of program management. The role produces communication that equips leadership to make timely, well-informed decisions.

RESPONSIBILITIES

Portfolio Health & Oversight

• Maintain an accurate, independent view of status, risk, and value across all programs in the Global AI portfolio at any given time.

• Establish program status by assessing reported progress against actual delivery, working across program leads, delivery teams, and key IT partners.

• Run the Global AI Portfolio governance and reporting cadences that keep multiple concurrent programs on track, and bring leadership clear, actionable recommendations.

• Identify program risks early and design mitigation plans, establishing mitigation ownership with the teams and partners best positioned to act.

• Build and maintain the portfolio risk framework, including how risks are identified, prioritized, owned, and escalated.

Flagship Program Delivery Oversight

• Own the delivery outcome of one of Chubb's highest priority AI programs, staying close enough to its progress across data, model, and application layers to assess real status.
• Own the governance of the program and engage directly on the matters that most affect the outcome: the risks that require negotiation, the issues that require resolution, and the decisions that require senior judgment. Delivery teams manage day-to-day execution; this role is accountable for the program shipping on time and meeting its targets.

Communication & Stakeholder Engagement

• Produce executive-standard communication that turns complex, cross-program activities into a clear, decision-ready narrative, distinguishing meaningful progress on outcomes and identifying what requires a decision.

• Deliver reporting, updates, and briefs of a quality that stands on its own before senior leaders.

• Coordinate across product and engineering teams, aligning stakeholders with competing priorities and holding them to their commitments through influence 

Frameworks, Standards & Continuous Improvement

• Define and evolve how AI programs are governed, delivered, and measured as the portfolio scales, raising the standard of delivery across the team.

• Bring AI into the practice of program management, from status synthesis and risk analysis to forecasting and reporting, and grow its use across the team

Mentoring

• Support the growth of others on the team by sharing expertise and coaching on program management practice

WHAT SUCCESS LOOKS LIKE

• Leadership has a clear, current, and trusted view of status, risk, and outcomes across every Global AI program, and makes faster, better-informed decisions as a result

• Risks are identified and addressed before they affect delivery

• The flagship program ships on time and meets its targets

• AI programs are governed, delivered, and measured through a stronger, more scalable outcomes-based approach as the portfolio grows

• AI is embedded in how the team practices program management, raising the speed and quality of the work

QUALIFICATIONS & EXPERIENCE

• 10+ years of program or portfolio management experience; a strong sense of ownership of outcomes with direct responsibility for driving complex, cross-functional technology programs to delivery 

• Experience both operating inside a large, matrixed, global enterprise and delivering enterprise-scale programs, with a track record of navigating complexity across functions and markets.

• A record of owning complex delivery challenges end to end, pairing strong delivery discipline with genuine accountability for outcomes.

• A record of owning ambiguous, open-ended problems and defining the approach to solve them.

• Exceptional executive communication skills, with a track record of turning complex, cross-program detail into clear, decision-ready reporting for senior leadership.

• Demonstrated ability to build governance, risk, and reporting frameworks from the ground up and embed them into how teams work.

• Hands-on engagement with AI and a track record of actively exploring how to apply it.

• Mastery of stakeholder engagement, influencing, and alignment across teams and partners outside the reporting line, with the ability to build trust quickly.

• Sound judgment to operate above the detail and manage the portfolio as a whole while retaining strong execution discipline.

• Sufficient understanding of the AI delivery lifecycle to govern delivery and assess risk.

• Experience managing and developing team members.

• Proficiency with program tracking, collaboration, and business intelligence tools (e.g., JIRA, Confluence, Power BI).

PREFERRED

• Experience applying AI directly to project or program management, with specific examples of how it has changed the way you manage programs

• Experience partnering with Finance on budgeting, forecasting, or value measurement.

• Experience in insurance or financial services.

• Program or project management certification (e.g. PMP) an asset.

Chubb Canada does not use artificial intelligence (AI) tools to assess, screen, or select applicants.

At Chubb we are committed to providing equal employment opportunities to all employees and applicants. It is our policy to provide equal employment opportunities to employees and applicants based on job-related qualifications and ability to perform a job.  If you require an accommodation during the hiring process or upon hire, please inform Human Resources.  If a selected applicant requests accommodation during the recruitment process, Chubb will consult with the applicant in order to provide suitable accommodation that takes into account the applicant's accessibility needs.