Senior Underwriting Specialist – Commercial Auto - 9849

DGA Careers Inc.; Toronto; Hybrid; CAD 90,000 - 120,000; Full time

Job summary

A prominent insurance organization in Canada is seeking a Senior Underwriting Specialist to manage complex transportation and corporate fleet risks. This hybrid role emphasizes mentorship and leadership within a high-performing team. Candidates should have over 10 years of commercial auto underwriting experience and strong negotiation skills. A competitive salary plus benefits and bonuses are provided.

Benefits

Competitive salary

Benefits

Pension plan

Bonus and share plan

Qualifications

• 10+ years of commercial auto underwriting experience.
• Strong leadership, mentoring, and decision-making skills.
• Excellent negotiation and communication abilities.

Responsibilities

• Lead underwriting of transportation and corporate fleet risks.
• Negotiate innovative solutions with brokers and clients.
• Analyze loss trends and design risk mitigation programs.
• Provide coaching and mentoring to colleagues.
• Conduct compliance reviews and support underwriting excellence.

Skills

Commercial auto underwriting experience

Strong leadership skills

Negotiation abilities

Communication skills

Collaborative mindset

Education

FCIP designation (or progress towards it)

Post Secondary Education

Job description

Senior Underwriting Specialist – Commercial Auto | Toronto (Hybrid)

Are you a seasoned commercial auto underwriter ready for your next big challenge? This is your chance to take on complex, high-profile accounts and make a real impact within a top-tier insurance organization.

We’re looking for a Senior Underwriting Specialist to join a high-performing Corporate Risk team in downtown Toronto (hybrid). In this role, you’ll take the lead on underwriting major transportation and corporate fleet risks while also mentoring the next generation of underwriting talent.

Why This Role Stands Out

• Work on complex, large-scale risks that keep your skills sharp and your expertise in demand.
• Collaborate directly with brokers, clients, and risk consultants to deliver smart solutions.
• Be recognized as a technical expert and mentor, shaping the growth of the team.
• Step into a role with visibility and influence across underwriting, risk management, and broker relationships.

What You’ll Be Doing

• Lead the underwriting of transportation and corporate fleet risks, including risk-managed accounts.
• Negotiate innovative solutions with brokers and clients.
• Analyze loss trends and design programs that mitigate future risk.
• Provide coaching, mentoring, and technical training to colleagues.
• Conduct compliance reviews and support underwriting excellence across the team.
• Build lasting relationships with brokers, clients, and reinsurers.

What You’ll Bring

• 10+ years of commercial auto underwriting experience.
• FCIP designation (or progress towards it) strongly preferred.
• Strong leadership, mentoring, and decision-making skills.
• A proven track record in complex or risk-managed accounts.
• Excellent negotiation and communication abilities.
• A collaborative, solutions-driven mindset.

Compensation

Competitive salary, benefits, pension plan, attractive bonus and share plan.

DGA Careers has been proudly serving the Canadian insurance industry for over 30 years, specializing in providing insurance recruiting services to major insurers, insurance brokerage firms and independent adjusting firms. With offices in Toronto, Vancouver, Montreal, Edmonton, and Calgary, DGA Careers is well positioned to conduct searches with a national scope. Our unrivalled professional network across Canada provides us with the ability to reach vital key influencers and passive candidates nationally.

Interested candidates please contact Maurice Reichberg at DGA Careers. If you are working with another DGA recruiter, feel free to ask them about this position.

Education Required

FCIP - Partial Completion
Post Secondary Education