Commercial Insurance Underwriting, New Graduate Rotational Program

We are seeking highly motivated and talented individuals to join our Commercial Insurance Underwriting New Graduate Rotational Program. This program is designed for students who are graduating soon or who have graduated within the last two years (Internal Definity employees must have graduated within the past five years and have been in their role for no longer than 15 months).

Commercial Insurance Underwriters play a critical role in evaluating risk, assessing business operations, determining appropriate coverage solutions, developing pricing strategies, and building strong broker partnerships that support profitable growth. Underwriters may specialize in a wide range of Commercial Insurance segments including property, liability, automobile, specialty, financial lines, energy, construction, transportation, and other industry sectors. This requires the ability to understand diverse business models and risk exposures. Successful underwriters combine strong analytical and financial skills with sound business judgment, relationship-building capabilities, and a customer-focused mindset.

As a participant in the program, you will gain valuable experience and develop a strong foundation across multiple Commercial Insurance business units through a structured rotational experience tailored to your individual development journey and business needs.

The program includes a structured learning plan, extensive networking and social opportunities, formal and informal mentorship, and exposure to business leaders across Commercial Insurance. Through hands-on experience, coaching, and meaningful work assignments, you'll contribute to the success of the business while developing the knowledge, skills, and professional relationships needed for a rewarding underwriting career.

When your program is complete, you'll have developed broad business knowledge of the company’s operations and strategic execution. You will gain new skills and insights, underwriting expertise, strong industry relationships, excellent growth opportunities, and a deeper understanding of Commercial Insurance. Upon successful completion of the program, participants are expected to transition into a permanent role within a Commercial Insurance business area supported during their rotations. Beyond developing technical underwriting capabilities, participants will gain exposure to business operations, strategic planning, transformation initiatives, and collaborative projects, helping you build a well-rounded understanding of the Commercial Insurance industry and the drivers of business success.

Rotational Program Length:

Two years, consisting of 2 to 5 rotational placements across Commercial Insurance business units. Rotations will be determined based on each participant's personalized development journey, career aspirations, performance, and business needs.

Potential Rotation Business Areas:

• Underwriting Processing

• Auto and Property Processing

• Small & Medium Enterprise (SME) Underwriting

• Mid-Market Underwriting

• Specialty Property & Energy

• Financial Lines

• Commercial Insurance Projects and Strategic Initiatives

What can you expect in this role?

Underwriting Processing & Operational Foundations

• Develop a strong understanding of commercial underwriting processes, workflows, systems, and guidelines.

• Support a variety of underwriting and policy processing activities while maintaining quality and productivity standards.

• Partner with Underwriters, Technical Processing teams, and operational stakeholders to ensure work is completed accurately and efficiently.

• Build foundational knowledge of commercial insurance products, risk evaluation, and policy administration.

Commercial Underwriting

• Assess risks and evaluate new business submissions, policy changes, and renewals.

• Determine appropriate pricing, coverage, and terms while applying sound underwriting judgment and corporate guidelines.

• Leverage tools, reports, data, and market intelligence to support underwriting decisions.

• Analyze financial information and business operations to understand risk exposures and profitability considerations.

• Build expertise in underwriting principles, risk selection, coverage structures, and portfolio management.

Broker Relationship Management & Business Development

• Build and maintain strong relationships with brokers and business partners.

• Communicate underwriting decisions, negotiate terms and conditions, and provide exceptional service through every interaction.

• Develop sales, negotiation, and influencing skills while contributing to profitable growth objectives.

• Support regional and business unit goals through a customer-focused and solution-oriented approach.

Specialty Underwriting & Advanced Risk Assessment

• Gain exposure to more specialized and complex commercial risks across various industries and market segments.

• Develop an understanding of specialty coverages, rating methodologies, reinsurance concepts, and risk hazards.

• Collaborate with senior underwriters and subject matter experts to evaluate complex underwriting situations.

• Strengthen analytical and decision-making capabilities while expanding industry and product knowledge.

Projects, Strategy & Continuous Improvement

• Participate in business initiatives, process improvement projects, and operational excellence activities.

• Support the development and monitoring of key performance indicators, reporting, and business insights.

• Contribute to initiatives that enhance underwriting effectiveness, customer experience, and operational efficiency.

• Collaborate with cross-functional teams including Claims, Risk Services, Operations, Product, and Distribution.

What do you bring to the role?

• A degree or diploma in Business, Economics, Finance, Commerce, Mathematics, Risk Management, or another relevant discipline with strong academic performance.

• Strong financial acumen and an interest in understanding business operations, profitability, and risk management.

• A strong business mindset with the ability to balance customer needs, risk selection, and organizational goals.

• Demonstrated analytical thinking, critical problem-solving, and decision-making capabilities.

• Excellent written and verbal communication skills.

• Strong interpersonal skills with the ability to build relationships and influence stakeholders.

• Goal-oriented, self-motivated, and driven to achieve results.

• Curiosity, initiative, and a desire to continuously learn and grow.

• A collaborative approach and ability to work effectively within diverse teams.

• Flexibility and adaptability in a fast-paced and evolving business environment.

• Commitment to obtaining your Chartered Insurance Professional (CIP) designation and other industry designations relevant to your rotational experience.

Application Process:

Submit your cover letter, resume, and academic transcripts (official or unofficial) as a single PDF document under the resume section online by September 25, 2026.

Interview:

As part of our first-round selection process, you will be asked to complete a one-way video assessment through Harver, our digital screening platform.

Candidates invited to the final round will participate in an in-person interview at our Toronto or Waterloo office location.

If you have any questions about Definity's Graduate Rotational Programs, contact our Campus Recruitment team at campusrecruiting@definity.com.

Salary Range: $51,300 - $94,400

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.

As part of Definity’s commitment to reconciliation, we acknowledge that our work, meetings, and travel take place on the lands now known as Canada, and recognize the enduring presence, wisdom, and stewardship of the First Nations, Métis, and Inuit peoples who have long cared for these lands.

Background checks

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

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