Digital Underwriting Product Lead

As a Digital Underwriting Product Lead, you will collaborate with underwriting teams, product line leaders, and technology partners to develop and enhance digitized specialty commercial products. You will play a key role in expanding our digital product portfolio, particularly in professional risks, CGL, EIL, and SME-targeted offerings, while also contributing to portfolio-level underwriting strategies, technical underwriting frameworks, and profitability analysis. The Opportunity:We are looking for a Digital Underwriting Product Lead to join our Digital Underwriting Team. What you'll be doing:Product Development & StrategyLead 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 AnalysisGather, 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 UnderwritingCollaborate 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 ManagementHelp monitor performance and KPI analysis to evaluate digital product and digital portfolio profitabilityPartner with actuarial and finance teams to develop profitability forecasts and support strategic decision-making. Product Design & DigitizationTranslate 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 CollaborationWork 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 & CommunicationFacilitate 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 furtherWhat’s in it for you:A great starting salary plus annual bonus potential & strong benefits package20 vacation days plus additional floater days per yearFantastic company RRSP, extended health and dental coverage, life insurance, travel insurance, vision care and wellness initiativesHybrid Work Environment - 3 days per week in the officeThere 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.#LI-Hybrid