Lead, AI Strategy
2 days ago
ABOUT CHUBB:
Chubb is a world leader in insurance. With operations in 54 countries, Chubb provides commercial and personal property and casualty insurance, personal accident and supplemental health insurance, reinsurance and life insurance to a diverse group of clients. The company is distinguished by its extensive product and service offerings, broad distribution capabilities, exceptional financial strength, underwriting excellence, superior claims handling expertise and local operations globally.
JOB SUMMARY:
Reporting directly to the VP of AI Programs, Strategy & Operations, the Lead, AI Strategy is a high-impact individual contributor responsible for helping drive Leadership alignment, execution clarity of strategic AI initiatives, and effective AI enablement at Chubb. This individual is a skilled strategist who bridges the gap between AI strategy and execution by focusing on detailed strategic planning, discovery work, and enablement activities required to align AI initiatives with Chubb's business objectives. The Lead will engage directly with both technical teams and business stakeholders to develop strategic plans, operating models, business cases, discovery reports, and operational reports.
Success will be measured by the effective enablement of the Global AI Leadership Team's decision-making and execution, accelerated adoption of the global AI platform, standards and frameworks, and operational excellence.
MAJOR RESPONSIBILITIES:
Strategy Development, Research and Analysis (50%)
- Partner with the VP to drive strategic alignment and develop Executive/Board-level presentations that support strategic discussions and decision-making
- Conduct discovery exercises and rapidly distill findings, insights and recommendations into executive-ready deliverables
- Develop business cases, detailed cost-benefit analyses and strategic roadmaps in collaboration with key stakeholders
- Lead the development of a scorecard that effectively tracks achievement of strategic AI objectives; support its operationalization approach
- Stay informed about external trends and best practices to bring outside insights into strategy
Change Enablement (30%)
- Act as a strategic partner to key stakeholders, advocating for win-win opportunities between business needs and technical/operational constraints
- Lead change enablement initiatives within the Global AI/ML Engineering Chapter, fostering collaboration and community
- Support internal enterprise-wide efforts that drive the adoption of AI technologies within the organization, focusing on people and process enablement
Operations & Reporting (20%)
- Proactively identify and implement opportunities to continuously improve enablement practices and day-to-day operations
- Prepare operational/program reports to support effective strategic decision-making
- Support governance and operational activities across the global AI portfolio
QUALIFICATIONS:
Must have:
- Bachelor's degree in engineering or a related STEM field, Master's degree in STEM or MBA preferred
- 5-7 years of experience in management consulting or business roles in which you developed current state analyses, business cases, strategic plans and scorecards, and executive summaries, while executing on project objectives in an enterprise setting
- Proven experience in developing practical deliverables and execution plans by drawing on a broad toolbox of strategy frameworks and practices
- Experience in leading digital/AI change management initiatives in an enterprise setting
- Highly comfortable with ambiguity and in dynamic environments; demonstrated experience in taking abstract concepts and developing recommendations through research and stakeholder consultation
- Proven problem-solving capabilities with a proactive approach, focus on outcomes, and an aptitude for first principles thinking
- Demonstrated ability in bridging technical and business concepts, with experience in effectively communicating new concepts/business implications to various audiences through written and oral formats
- Strong interpersonal and stakeholder facilitation skills, with demonstrated ability to adapt communication/collaboration approaches across diverse work styles
Nice to have:
- 7-10 years of experience in management consulting or a similar business role focused on the property & casualty insurance sector; demonstrated progression in role
- Experience in a highly regulated industry such as financial services or insurance
- Experience in leading business cases or client pursuits, with demonstrated success in obtaining Executive alignment
- Experience in leading Generative AI/Agentic AI projects, from scope definition to execution
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.
-
Lead, AI Strategy
5 days ago
Toronto, Ontario, Canada Chubb Full time $120,000 - $180,000 per yearDescriptionChubb is a world leader in insurance. With operations in 54 countries, Chubb provides commercial and personal property and casualty insurance, personal accident and supplemental health insurance, reinsurance and life insurance to a diverse group of clients. The company is distinguished by its extensive product and service offerings, broad...
-
Ai Business Strategy and Architecture Lead
2 weeks ago
Toronto, Ontario, Canada BMO Full time US$132,000 - US$231,000 per yearOperates at a group level and serves as a senior specialist resource across Wealth Management.Influences how teams/groups work together.Applies expertise and thinks creatively to address unique or ambiguous situations and to find solutions to multiple, interdependent, complex problems.Communicates abstract concepts in simple terms.Fosters strong internal and...
-
Ai Business Strategy and Architecture Lead
2 weeks ago
Toronto, Ontario, Canada BMO Full time $132,600 - $231,000Application Deadline:10/26/2025Address:100 King Street West Job Family Group:Data Analytics & ReportingOperates at a group level and serves as a senior specialist resource across Wealth Management. • Influences how teams/groups work together. • Applies expertise and thinks creatively to address unique or ambiguous situations and to find solutions...
-
AI Strategist
6 days ago
Toronto, Ontario, Canada Siena AI Full time $80,000 - $120,000 per yearMeet SienaSiena is the first intelligence layer for customer experience. We're creating an operating system of AI agents that learn, remember, and act across every customer touchpoint—from support conversations to shopping experiences to voice and social media interactions.Siena doesn't just automate support; it powers shopping agents, builds persistent...
-
AI Strategist
5 days ago
Toronto, Ontario, Canada Siena AI Full time $80,000 - $120,000 per yearMeet Siena Siena is the first intelligence layer for customer experience. We're creating an operating system of AI agents that learn, remember, and act across every customer touchpoint—from support conversations to shopping experiences to voice and social media interactions. Siena doesn't just automate support; it powers shopping agents, builds...
-
Manager, AI Strategy
2 weeks ago
Toronto, Ontario, Canada OMERS Full time $80,000 - $120,000 per yearChoose a workplace that empowers your impact. Join a global workplace where employees thrive. One that embraces diversity of thought, expertise and experience. A place where you can personalize your employee journey to be — and deliver — your best. We are a purpose-driven, dynamic and sustainable pension plan. An industry leading global investor with...
-
Manager, AI Strategy
2 weeks ago
Toronto, Ontario, Canada OMERS Full time $120,000 - $180,000 per yearChoose a workplace that empowers your impact.Join a global workplace where employees thrive. One that embraces diversity of thought, expertise and experience. A place where you can personalize your employee journey to be — and deliver — your best.We are a purpose-driven, dynamic and sustainable pension plan. An industry leading global investor with teams...
-
Toronto, Ontario, Canada RBC Full time $120,000 - $180,000 per yearJob DescriptionLead Data Scientist, AI and Technology Strategy, TEOWhat is the opportunity?As Lead Data Scientist, this role will collaborate closely with the Director, AI and Technology Strategy, TEO, to develop and implement TEO's AI and data strategy. The AI and Technology Strategy team holds primary accountability for driving the adoption and value...
-
Innovation Strategy Lead
2 weeks ago
Toronto, Ontario, Canada BMO Full time $80,000 - $120,000 per yearWe are seeking a forward-thinkingInnovation Strategy Leadto guide enterprise transformation through Insure AI, Agentic AI, technology innovation, and modernization across our Institutional, Retail, and Advisory business lines. This role is key to strengthening proactive innovation, delivering measurable business performance, and ensuring sustainability of...
-
Innovation Strategy Lead
2 weeks ago
Toronto, Ontario, Canada BMO Full time $69,000 - $129,000Application Deadline:12/10/2025Address:250 Yonge Street Job Family Group:Strategy & ChangeWe are seeking a forward-thinking Innovation Strategy Lead to guide enterprise transformation through Insure AI, Agentic AI, technology innovation, and modernization across our Institutional, Retail, and Advisory business lines. This role is key to strengthening...