Executive Underwriter – Mid-Market Commercial - 247

DGA Careers Inc.; Toronto; Hybrid; CAD 100,000 - 140,000; Full time

Benefits offered by this job

Employer-matched RRSP

Employee share purchase program

Comprehensive health and dental

Flexible hybrid schedule

Job summary

DGA Careers Inc. in Toronto is seeking an Executive Underwriter – Mid-Market Commercial to lead complex mid-market accounts within a hybrid Toronto office. The role emphasizes hands-on underwriting, mentoring juniors, and potential people leadership.

You’ll manage profitable growth with brokers, develop risk solutions, and contribute to portfolio strategy. Prerequisites include 7+ years of Canadian P&C underwriting, a Bachelor’s degree with CIP, strong negotiation and English proficiency, and

Qualifications

• 7+ years P&C underwriting in Canada with complex mid-market risks.
• Bachelor’s degree and CIP; FCIP preferred.
• Strong broker relationships and portfolio growth track record.
• Ability to mentor underwriters and travel occasionally.

Responsibilities

• Lead underwriting of complex mid-market risks within authority and risk appetite.
• Build, manage, and grow a profitable portfolio with growth and retention goals.
• Develop and maintain broker/client relationships as a trusted advisor.
• Act as senior technical authority on structure, pricing, and coverage.
• Coach and mentor underwriters and support their development.
• Contribute to underwriting appetite, portfolio initiatives, and distribution.
• Represent the organization at broker meetings and industry events.
• Maintain file accuracy, data quality, and regulatory compliance.
• Contribute to portfolio reporting and business planning.

Skills

P&C underwriting

Broker relationships

Mentoring

Pricing & risk assessment

Negotiation

MS Office

Underwriting systems

Education

Bachelor’s degree

CIP

Tools

MS Office

Underwriting software

Job description

Executive Underwriter – Mid-Market Commercial

Toronto, ON | Hybrid | Full-time, Permanent

About the Opportunity

Our client, a well-established international commercial and specialty insurer, is looking for a senior, production-focused underwriter to join its growing Canadian Mid-Market team. Reporting to the Head of Mid-Market, you will underwrite complex mid-size to large accounts, act as a senior technical resource for the team, and help shape the direction of the portfolio.

This is a hands-on underwriting role. You will write your own book, take referrals from colleagues, and mentor junior underwriters. Candidates who want to grow into people leadership will have the chance to take on a small team over time.

Why This Role

• Real underwriting autonomy. It's a specialist, boutique-style environment where decisions are made in-house, with very few referrals up the chain. You won’t be waiting on head office to respond to your broker.
• Specialty, complex risk. The focus is on manufacturing and other hazardous trades, with a minimum premium of $20,000, and the ability to offer both property and casualty.
• Strong backing. You'll have the stability of an A+ rated global insurance group with more than 100 years of experience in industrial insurance, combined with the agility of a smaller Canadian team.
• Room to grow. Take on mentorship and, if it's your goal, move into people management while continuing to underwrite.

Responsibilities

• Lead the underwriting of complex new and renewal mid-market risks within established authority and risk appetite
• Build, manage, and grow a profitable portfolio, with accountability for growth, retention, underwriting quality, and profitability
• Develop and maintain strategic relationships with brokers and clients as a trusted advisor on complex risks
• Act as a senior technical referral authority, advising on structure, pricing, coverage solutions, and risk selection
• Coach and mentor underwriters, supporting their development
• Contribute to underwriting appetite, portfolio initiatives, and distribution strategy
• Represent the organization at broker meetings, negotiations, industry events, and networking activities
• Maintain high standards of file accuracy, documentation, data quality, and regulatory compliance
• Contribute to portfolio reporting and business planning

Qualifications

• 7+ years of P&C underwriting experience in the Canadian market (10+ years preferred), including complex mid-market risks. Experience across both property and casualty is required, even if you are stronger in one line
• Manufacturing or other complex/hazardous trades experience is strongly preferred
• Advanced knowledge of P&C policy wordings, pricing, and risk assessment
• A proven record of profitable portfolio growth and strong broker relationships
• Demonstrated ability to mentor and influence other underwriters
• Bachelor’s degree and CIP required; FCIP preferred
• Strong negotiation, analytical, and commercial skills
• Excellent written and verbal communication skills in English; working knowledge of French is an asset
• Proficiency with underwriting systems and Microsoft Office
• Willingness to work a hybrid schedule (currently three days in the office) with flexibility as needs evolve, and to travel occasionally

What's Offered

• Salary range of $100,000-$140,000, based on experience, plus a performance bonus
• Employer-matched RRSP
• Employee share purchase program
• Comprehensive health and dental benefits