Senior Underwriting Specialist – Commercial Auto

DGA; Toronto; Hybrid; CAD 100,000 - 125,000; Full time

Job summary

A leading insurance organization in Toronto seeks a Senior Underwriting Specialist to manage complex commercial auto risks. This hybrid role involves mentoring talent and collaborating with brokers to deliver innovative solutions. The ideal candidate has over 10 years of experience in commercial auto underwriting, strong negotiation skills, and prefers candidates with FCIP designation.

Benefits

Competitive salary

Benefits

Pension plan

Attractive bonus

Share plan

Qualifications

• 10+ years of commercial auto underwriting experience.
• Strong leadership, mentoring, and decision-making skills.
• Proven track record in complex or risk-managed accounts.

Responsibilities

• Lead the underwriting of transportation and corporate fleet risks.
• Negotiate innovative solutions with brokers and clients.
• Analyze loss trends and design programs to mitigate risk.

Skills

Commercial auto underwriting experience

Leadership skills

Negotiation abilities

Communication skills

Decision-making skills

Education

FCIP designation (or progress towards it)

Post Secondary Education

Job description

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.

Information

• City : Toronto
• Market segment : Commercial Insurance
• Job Type : Hybrid
• Education : FCIP - Partial Completion, Post Secondary Education
• Expertise : Underwriting - Auto / Fleet
• Minimum experience required : 7 to 10 Years
• Contact name : Maurice
• Contact email :