Lead, AI Strategy

2 days ago


Toronto, Ontario, Canada Chubb Full time

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.



  • Toronto, Ontario, Canada Boam AI Full time

    Go from advising to building in the AI decade's defining roleBoam AI builds managed data agents that transform messy, unstructured signals from public, private, and proprietary sources into structured, reliable, and always up-to-date intelligence on millions of SMBs and enterprises worldwide. We deliver customized, decision-ready insight that gives our...


  • Toronto, Ontario, Canada BMO Full time

    Operates 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...


  • Toronto, Ontario, Canada BMO Full time $132,600 - $231,000

    Application Deadline:11/29/2025Address: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

    Meet 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

    6 days ago


    Toronto, Ontario, Canada Siena AI Full time

    Meet 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...


  • Toronto, Ontario, Canada BMO Full time

    We 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...


  • Toronto, Ontario, Canada BMO Full time $69,000 - $129,000

    Application 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...


  • Toronto, Ontario, Canada Software International Full time

    Software International (SI) supplies technical talent to a variety of clients ranging from Fortune 100/500/1000 companies to small and mid-sized organizations in Canada/US. We are currently hiring for a Business Strategy Lead - AI for our global IT M&A client in the GTA.Role: Business Strategy Lead - AIType: Fulltime, PermSalary Range: $130,000 - $140,000...

  • Social Media Lead

    6 days ago


    Toronto, Ontario, Canada Viggle AI Full time

    "Where cultural fluency becomes contagious."What We're Looking ForMastery of Social Storytelling & ViralityWe are looking for a marketer who is a master of building a brand's reach and relevance online. You have an instinct for virality and a deep understanding of what compels audiences to share. You know how to create cohesive, culturally relevant content...


  • Toronto, Ontario, Canada KData AI Full time

    Job Title: Agentic AI Platform EngineerClient: Banking ClientLocation:Downtown Toronto (On-site 4 days/week)Position Type:6-Month Contract (Renewable)Domain: Generative AI, Agentic Systems, AI Platform EngineeringRate: up to $90Role SummaryA leading Banking Client is building a next-generationAgentic AI Platformto enable scalable, enterprise-wide deployment...