Director, Commercial Transportation
Talent Acquisition Team at Westland Insurance. Text reply only. · CA
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About the Role
Westland Insurance Group Ltd. is seeking a dynamic commercial transportation leader to elevate its national Transportation portfolio. This leadership role is responsible for driving strategic growth, managing complex risks, and empowering a high-performing advisory team across Canada.
Responsibilities
- Lead and coach a team of Commercial Transportation Advisors and Account Managers to drive growth, retention, and high-quality client service
- Develop and execute strategic plans for the Commercial Transportation portfolio, ensuring strong alignment with corporate priorities
- Serve as a senior advisor to key clients, offering expert guidance on risk management, complex insurance placement, and regulatory compliance
- Build and maintain strong relationships with clients, carrier partners, and industry associations
- Drive new business development and retention strategies across Canada
- Partner with Underwriting, Claims, Sales, and Specialty teams to deliver innovative, comprehensive client solutions
- Monitor industry trends, regulatory changes, and emerging risks affecting transportation clients
- Represent Westland at national and regional industry events, conferences, and client meetings
- Ensure operational excellence and adherence to internal policies and external regulations
- Support continuous improvement through performance monitoring, coaching, and disciplined execution
Requirements
- 7–10 years of experience in commercial transportation insurance or a related field
- Proven leadership experience managing teams and complex client portfolios
- Deep understanding of transportation insurance products, regulatory frameworks, and risk management practices
- Strong business development and relationship management skills
- Excellent communication, negotiation, and presentation abilities
- Proficiency with Microsoft Office and CRM platforms
- Level 2 General Insurance License (or willingness to obtain)
- High degree of professional integrity with a commitment to delivering exceptional client experiences
- Entrepreneurial mindset with strong business acumen and a growth-oriented approach
Skills
- Commercial transportation insurance
- Leadership
- Team management
- Client portfolio management
- Transportation insurance products
- Regulatory frameworks
- Risk management
- Business development
- Relationship management
- Communication
- Negotiation
- Presentation
- Microsoft Office
- CRM platforms
Location
- Toronto, ON
Work Type
- Hybrid
Experience Level
- 7-10 years
Education Level
- Level 2 General Insurance License (or willingness to obtain)
- CIP, CAIB, or CRM designation considered an asset
Salary/Compensations
- $129,600 to $162,000
Benefits
- Competitive annual short-term incentive program
- Financial assistance for approved work-related training and development programs
- An open, flexible and welcoming workplace
- Plenty of opportunities to grow and learn
- Autonomy to drive your own success
- Inclusive culture
- A total rewards program that supports your financial, physical, and mental wellbeing
- Flexible paid Values Days
- Paid Volunteer Days
About the Company
- Westland Insurance Group Ltd. is growing.
- The Westland story is all about growth, and that means plenty of possibility for everyone on our team.
- Every day, Westland proves that building a great business means taking care of communities, clients, and each other with equal commitment.
- Westland is committed to continuous learning where employees can grow their potential and write the stories of their careers.
- We strive to be much more than a great place to work. Here, you join a collective of incredibly vibrant, purpose driven, and open-minded people.
- Westland Insurance Ltd. is an inclusive organization that values diversity in its workforce.
- We listen, champion equity and diversity, and create safe welcoming spaces where everyone has a voice and is free to be themselves.
Equal Opportunity
- Westland Insurance Ltd. encourages applications from all qualified individuals and will accommodate applicants' disability-related needs, up to the point of undue hardship, throughout all stages of the recruitment and selection process.
- If you require a disability-related accommodation in order to participate in the recruitment process, please contact the recruitment team by email at careers@westlandinsurance.ca