Underwriting Leader

Our client is a fast-growing MGA seeking a skilled Commercial Underwriting professional to join them and shape their next generation of leadership. Since 2020, our client has doubled in size and are on track to continue their growth trajectory. This is a fantastic opportunity for a qualified individual to take their career to the next-level!

Compensation

• $130,000 to $180,000 commensurate with experience

Benefits & Perks

• A real chance at succession and growth
• Comprehensive benefits coverage
• Generous paid time off
• Retirement Savings Plans
• Bonus and share options potential

Responsibilities

• Underwrite and manage a commercial book of business across specialty lines, making risk and pricing decisions in line with appetite and capacity guidelines
• Partner closely with the Chief Underwriting Officer during a structured transition period to absorb institutional knowledge and underwriting philosophy
• Identify and lead operational improvements—including reporting, workflow automation, and technology modernization—to drive efficiency across the MGA
• Build cross-functional relationships and influence outcomes across underwriting, claims, and risk services without relying on formal authority
• Support strategic initiatives including new product development, carrier/capacity partnerships
• Gradually assume broader leadership responsibilities over the Canadian operation as the business scales and the succession plan advances

Qualifications

• 5-8 years of experience in underwriting, actuarial, or analytical roles within an MGA or commercial carrier environment
• Strong commercial lines knowledge; experience in specialty lines (transportation, trucking, or related) is a significant asset
• Demonstrated commercial mindset—understands production, revenue generation, and the business of insurance, not just risk evaluation
• Comfortable with technology and data; experience with reporting tools, workflow automation, or AI integration is a plus
• Proven ability to influence and collaborate across teams without formal authority
• High degree of initiative and ownership—thrives in a flat, fast-paced, entrepreneurial environment
• CIP, FCIP, FCAS, or other relevant insurance or actuarial designation is preferred but not required
• Based in or willing to commute to the Hamilton/Toronto corridor

To be considered, applicants must be legally entitled to work in Canada, including holding any required permits. We believe diverse teams build stronger companies, and we welcome applicants from all backgrounds, experiences, and perspectives.