VP, AI Product Delivery

Location:- Toronto, ON

Travel : - ~40% - Travel to U.S. (East Coast)

Chubb is a world leader in insurance. With operations in 54 countries and territories, 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. As an underwriting company, we assess, assume and manage risk with insight and discipline.

We service and pay our claims fairly and promptly. The company is also defined by its extensive product and service offerings, broad distribution capabilities, exceptional financial strength and local operations globally. Parent company Chubb Limited is listed on the New York Stock Exchange (NYSE: CB) and is a component of the S&P; 500 index.

Chubb maintains executive offices in Zurich, New York, London, Paris and other locations, and employs approximately 40,000 people worldwide.

Additional information can be found at: www.chubb.com.

Overview

We're looking for a VP, AI Product Delivery, to lead the execution of AI-enabled underwriting capabilities, ensuring what gets built delivers real, measurable value to Chubb, globally.

This role sits at the intersection of product leadership and delivery accountability. You'll own the roadmap for a global portfolio of AI initiatives, shape how capabilities are designed and sequenced, and drive execution through to adoption and benefit realization.

You're not just moving work through a pipeline. You're making decisions that determine what gets built, why it matters, and whether it actually works in practice.

You'll bring deep underwriting domain knowledge, strong product instincts and delivery discipline - to sharpen solution design, and ensure every capability delivered creates tangible value across the underwriting lifecycle.

You'll partner closely with Senior product, engineering,



and underwriting leaders across a matrixed global organization, leading through influence and driving alignment on the priorities that matter most.

Success in this role means a portfolio of AI capabilities that are well-prioritized, well-built, adopted by underwriters, and delivering the outcomes the business expects.

MAJOR DUTIES & RESPONSIBILITIES:

- Own the product roadmap for AI capabilities globally (with a strong focus on underwriting), setting priorities based on business value, strategic fit, and delivery capacity.
- Shape solution design on these capabilities, bringing domain expertise and product judgment alongside engineering and product teams.
- Drive execution from build through deployment and into adoption, maintaining accountability for outcomes rather than outputs.
- Partner with Senior Product leaders and analysts across regions to align on scope, sequence work effectively, and keep the portfolio moving.
- Define clear success metrics for each capability and hold teams accountable to business value realization, not just feature delivery.
- Engage directly with underwriting leaders and business stakeholders to validate that capabilities meet workflow needs and are adopted in practice.
- Maintain visibility across portfolio risks, dependencies, and sequencing decisions, making trade-off calls and escalating where senior alignment is needed.
- Deploy and reallocate delivery capacity to accelerate the highest-priority capabilities without compromising quality.

QUALIFICATIONS:





- 15+ years of relevant experience, with a significant portion in product and delivery leadership roles in P&C; insurance; experience owning AI or digital product development in P&C; insurance is strongly preferred.
- A strong product mindset combined with a bias for execution: you set transparent outcomes, make prioritization calls decisively, and drive teams to deliver against them.
- Demonstrated ability to hold end-to-end accountability for a product portfolio, from roadmap definition through to benefit realization.
- Strong grasp of underwriting workflows and how AI capabilities create value across submission, risk assessment, pricing, and portfolio management.
- Experience shaping AI or data-driven product solutions, including working with data and engineering teams to evaluate feasibility and drive sound design decisions.
- Track record in managing complex, multi-initiative portfolios and making clear, well-reasoned prioritization decisions in fast-moving environments.
- Proven ability to lead and influence across a matrixed, globally distributed organization without direct line authority.
- Bachelor's degree in a relevant discipline required; advanced degree (e.g., MBA) is a plus.
- CIP, CPCU, or similar industry designation is preferred.

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.

📌 VP, AI Product Delivery (Toronto)
🏢 Chubb
📍 Toronto