Director, Commercial Transportation
About The Position
Westland Insurance Group Ltd. is seeking a dynamic commercial transportation leader to elevate its national Transportation portfolio as Director, Commercial Transportation. This leadership role is responsible for driving strategic growth, managing complex risks, and empowering a high-performing advisory team across Canada. The position is based in Toronto, ON, with travel as required. Westland is committed to continuous learning and offers financial assistance for approved work-related training and development programs. The company emphasizes growth, community care, client focus, and mutual support. This role involves leading advisory teams supporting complex commercial transportation risks, strengthening client relationships, navigating regulatory environments, and building innovative insurance solutions.
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
Nice To Haves
- CIP, CAIB, or CRM designation considered an asset
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
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
- Total rewards program that supports your financial, physical, and mental wellbeing
- Flexible paid Values Days to celebrate days important to you
- Paid Volunteer Days
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
