Executive Underwriter - Mid-Market Commercial (Property & Casualty) 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 risksDevelop 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

#J-18808-Ljbffr

📌 Executive Underwriter (Winnipeg)
🏢 DGA Careers
📍 Winnipeg