Join a highly respected and well-established insurance provider that is deeply committed to both its clients and its employees—offering a supportive, growth-oriented environment where people come first. This is a high-impact leadership role focused on driving strategic regional growth while leading and mentoring a team of Commercial Insurance Specialists. The District Sales Manager plays a key role in expanding the team’s book of business, supporting individual development, and maintaining strong client relationships. Ideal candidates bring deep commercial insurance expertise, a collaborative mindset, and a passion for leading high-performing sales teams.

Roles and Responsibilities

• Lead, coach, and develop a team Commercial Insurance Sales Agents across the GTA.

• Actively contribute to regional growth through both leadership and personal sales contributions

• Guide newer agents in building their books and help more seasoned team members maintain momentum and productivity.

• Drive business development through cold calling, in-person networking, door-knocking, and relationship building with commercial groups and local businesses.

• Collaborate with senior leadership to execute the regional sales strategy and performance objectives.

• Ensure regional alignment with company goals and promote a strong, results-oriented sales culture.

Qualifications and Skills

• Minimum 5 years of experience in commercial insurance, ideally in a field sales or business development role.

• Proven ability to lead, mentor, and motivate sales professionals of varying experience levels.

• Strong interpersonal and networking skills with a hunter mentality and resilience in a highly competitive, low-lead environment.

• Comfortable with extensive in-person sales activity, including travel within the assigned territory (vehicle required).

• Commercial insurance licensing required: OTL and LLQP (RIBO also accepted; expired licenses may be supported for renewal).

Education

• Post-secondary education preferred (college or university).

• Completion of industry certifications considered an asset.

Nice-to-Haves

• Experience insurance organizations with both direct-to-consumer and traditional commercial arms

• Prior success in highly independent sales roles with limited inbound lead support.

• Previous leadership experience in an environment emphasizing field sales and territory growth.

• Exposure to claims or underwriting considered a plus.

Benefits

• Competitive compensation structure with performance-based bonuses and commission opportunities.

• Comprehensive health and dental benefits from day one.

• Retirement savings programs with employer contributions.

• Employee share purchase plans and staff discounts on insurance products.

• Generous paid time off, including vacation, personal days, and wellness days.

• Hybrid work model with flexibility to balance in-office and field responsibilities.

• Opportunities for professional development, leadership training, and internal mobility.