Digital Underwriting Product Lead

Markel; Toronto; Hybrid; CAD 80,000 - 100,000; Full time

Job summary

A leading insurance company is seeking a Digital Underwriting Product Lead in Toronto to develop and manage digital insurance products. You will oversee product development, gather requirements, and collaborate with cross-functional teams. Ideal candidates will have over 5 years of experience in product analysis, a strong analytical background, and proficiency in digital product management. This role offers a hybrid working environment, a competitive salary, and a comprehensive benefits package.

Benefits

Competitive starting salary

Annual bonus potential

Strong benefits package

20 vacation days plus floater days

Hybrid work environment

Qualifications

• 5+ years of experience in business or product analysis in professional liability.
• Experience in digital product management within the insurance or fintech sector.
• Strong analytical and data interpretation skills.

Responsibilities

• Lead the end-to-end development of digital insurance products.
• Gather, document, and validate business and functional requirements.
• Collaborate with underwriting leadership to define portfolio strategies.

Skills

Business analysis

Digital product management

Stakeholder management

Analytical skills

Agile methodologies

Project leadership

Education

CIP designation or working towards

Additional designations (FCIP, CRM, ACII)

Tools

Underwriting analytics tools

COR pack analysis

Job description

The Opportunity:

We are looking for a Digital Underwriting Product Lead to join our Digital Underwriting Team.

What you’ll be doing:

Product Development & Strategy

• Lead the end-to-end development of digital insurance products, from ideation to launch, with a focus on scalability and automation.
• Define and manage product backlogs, ensuring alignment with underwriting and business priorities.

Insurance Product Ownership & Business Analysis

• Gather, document, and validate business and functional requirements for digital insurance products across lines such as CGL, EIL, and professional risks.
• Translate complex insurance concepts into clear, actionable user stories, epics, and acceptance criteria for development teams.
• Collaborate with cross-functional teams to ensure requirements are understood, feasible, and aligned with regulatory and compliance standards.
• Serve as the primary liaison between underwriting, actuarial, technology, and operations teams to ensure shared understanding of product goals and delivery timelines.

Portfolio & Technical Underwriting

• Collaborate with underwriting leadership to define and refine portfolio underwriting strategies, including risk appetite, pricing adequacy, and performance monitoring.
• Support the development of technical underwriting guidelines, rating models, and risk segmentation strategies for digital products.
• Utilize data analytics to monitor portfolio performance, identify trends, and recommend corrective actions.

Performance Management

• Help monitor performance and KPI analysis to evaluate digital product and digital portfolio profitability.
• Partner with actuarial and finance teams to develop profitability forecasts and support strategic decision-making.

Product Design & Digitization

• Translate traditional insurance products into digital formats, including digitizing wordings, underwriting question sets.
• Partner with product line leaders and data scientists to build and validate pricing models and underwriting rules.
• Ensure digital products meet compliance, regulatory, and governance standards.

Cross-Functional Collaboration

• Work closely with technology vendors, operations, and senior management to ensure seamless product delivery and integration.
• Coordinate with global Markel teams to assess localization opportunities for international digital products.
• Lead UAT and quality assurance testing for digital product releases, ensuring alignment with user stories and business requirements.

Stakeholder Engagement & Communication

• Facilitate regular stakeholder meetings to gather feedback, share updates, and align on priorities.
• Develop training materials and lead internal product rollouts to ensure adoption and understanding.
• Define and track KPIs to measure product success and inform future enhancements.

Our must haves:

• 5+ years of experience in business or product analysis in professional liability and specialty commercial underwriting, with exposure to portfolio management, technical underwriting, and profitability analysis.
• Experience in digital product management within the insurance or fintech sector.
• CIP designation or working toward it; additional designations (e.g., FCIP, CRM, ACII) are an asset.
• Strong analytical and data interpretation skills; experience with underwriting analytics tools and COR pack analysis is a plus.
• Proficiency in product lifecycle management, agile methodologies, and digital transformation initiatives.
• Excellent communication, stakeholder management, and project leadership skills.
• Ability to work independently and collaboratively in a fast-paced, evolving environment.
• A passion for innovation, customer‑centric design, and continuous improvement.

Who we are:

Markel Group (NYSE – MKL) a Fortune 500 company with over 60 offices in 20+ countries, is a holding company for insurance, reinsurance, specialist advisory and investment operations around the world.

We’re all about people | We win together | We strive for better | We enjoy the everyday | We think further

What’s in it for you:

• A great starting salary plus annual bonus potential & strong benefits package
• 20 vacation days plus additional floater days per year
• Fantastic company RRSP, extended health and dental coverage, life insurance, travel insurance, vision care and wellness initiatives
• Hybrid Work Environment - 3 days per week in the office
• There are countless opportunities to learn new skills and develop in your career and we can provide the support needed to do just that!

Are you ready to play your part?

Choose ‘Apply Now’ to fill out our short application, so that we can find out more about you.

Markel celebrates the value of a diverse workforce that brings experience and expertise from a wide variety of backgrounds and life circumstances. Whatever your background or location in Canada if you feel you meet the requirements of this role then we want to hear from you. We are also happy to consider candidates who are looking for flexible working patterns.

We are a Disability Confident Committed employer, which means you'll have a positive experience applying for a role at Markel and are able to perform at your best. If there are any adjustments we can reasonably make to ensure that the process is accessible for you at every stage please let us know. We will ensure that individuals with disabilities are provided with all reasonable accommodations to be able to participate in the job application or interview process and to perform essential job functions if successful. Please contact us to request any accommodations that may be needed.

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