Impress employers and recruiters.
Choose from hundreds of resume examples.
Impress employers and recruiters.
Choose from hundreds of resume examples.
Target Resume Now
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