Director, Digital Product and Underwriting [HYBRID]
Toronto, ON
Canada
Category
Digital Media
Experience Required
Yes
Degree Required
Yes
Employment Type
Employee
Work Schedule
Full-Time
Job Description
Definity is the parent company to some of Canada’s most long-standing and innovative insurance brands, including Economical Insurance, Sonnet Insurance, Family Insurance Solutions, and Petline Insurance. Our ambition is to be one of Canada’s leading and most innovative property and casualty insurers. We can’t do that without our people, so we embrace and encourage a culture that’s collaborative, ambitious, rewarding, and empowering. 
We offer a flexible, hybrid work experience where employees work from the office and virtually depending on the type of work they are doing and who they are working with. Bring your true self and be a part of our journey. It’s better here. 

Reporting to the AVP, Product and Underwriting, the role is responsible for leading strategic development and execution of underwriting policies, practices, and risk management for direct-to-consumer home and auto insurance products. This role ensures profitable growth, regulatory compliance, and competitive customer-centric products while fostering innovation in a digital-first environment.

What can you expect 

Strategic Leadership

  • Develop and implement underwriting strategies aligned with company operational plan and market trends.
  • Lead underwriting initiatives to optimize pricing, risk selection, and portfolio performance.
  • Monitor competitive landscape and regulatory changes to inform product innovation and differentiation.
  • Collaborate with executive leadership on product development and market expansion.

Operational Oversight

  • Oversee day-to-day underwriting philosophy, ensuring efficiency, accuracy, and compliance.
  • Monitor underwriting guidelines, workflows, and quality assurance protocols.
  • Set performance goals, conduct evaluations, and implement training programs.
  • Foster a culture of accountability, innovation, and continuous improvement.

Technology & Innovation

  • Partner with product and tech teams to enhance underwriting automation and digital tools.
  • Leverage data analytics and AI to improve risk assessment and decision-making.
  • Drive adoption of modern underwriting platforms and customer-centric solutions.

Stakeholder Collaboration

  • Work cross-functionally with digital, product, portfolio management, pricing, claims, marketing, analytics and legal teams.
  • Represent underwriting in strategic planning, regulatory discussions, and partner engagements.
  • Provide insights and reporting to senior leadership on underwriting performance and competitive landscape.
 
Job Requirements
What do you bring

Bachelor’s degree in business, Insurance, Actuarial Science, or related field (MBA or CIP/FCIP designation is an asset)
8+ years of progressive experience in personal insurance, with a strong focus on product management and underwriting
Proven leadership experience in a direct-to-consumer or digital insurance environment
Strong collaboration skills, strategic thinking and stakeholder management
Deep understanding of home and auto insurance products, pricing, and regulatory frameworks
Excellent analytical and problem solving with the ability to select and implement best solution
Advanced decision-making skills
Strong proficiency in Microsoft Office suite of products
Key Competencies

Strategic Thinking & Execution
Risk Management & Compliance
Leadership & Team Development
Customer-Centric Mindset
Digital Fluency & Innovation
Collaboration & Influence
Salary Range: $134,300 - $184,300

Actual salary for the role may vary depending on work location of the successful candidate and other factors including but not limited to, skills, education, experience, working conditions and the local labour market.

This position is being posted to fill an existing vacancy.

Interested in this role, but don’t meet every requirement? We encourage you to apply! We know from experience that a candidate doesn’t need 100% of the qualifications listed to bring incredible value to our team. We’re actively seeking diverse backgrounds and perspectives to help us make insurance better. At Definity, inclusion, diversity, and equity aren’t just “nice to have” — they’re essential to our success.

What’s in it for you?

Hybrid work schedule for most roles
Company share ownership program
Incentive Program - Eligible employees may participate in various incentive plans which are paid out at the discretion of the company and subject to individual and company performance.
Pension and savings programs, with company-matched RRSP contributions
Paid volunteer days and company matching on charitable donations
Educational resources, tuition assistance, and paid time off to study for exams
Focus on inclusion with employee groups, support for gender affirmation surgery, access to BIPOC counsellors, access to programs for working parents
Wellness and recognition programs
Discounts on products and services
Go ahead and expect a lot — you deserve it.

It’s better here — but don’t take our word for it. Definity was named by Great Place to Work® as one of the Best Workplaces™ in Canada for women, for youth, and for inclusion.

Our inclusive work environment welcomes diversity and supports accessibility. If you require accommodation at any time during the recruitment process, please let us know by contacting accessibility@economical.com.

Background checks

This role requires successful clearance of background checks (including criminal checks and leadership references).

#LI-Hybrid

#IND1