We're searching for a Director, Commercial Transportation. Are you searching for new possibilities?

Westland Insurance Group Ltd. is growing, and we're looking for a dynamic commercial transportation leader to elevate our national Transportation portfolio as Director, Commercial Transportation (Hybrid). This leadership role is responsible for driving strategic growth, managing complex risks, and empowering a high-performing advisory team across Canada. This position is based in Toronto, ON, with travel as required.

Expected Compensation: The expected hiring range for this role is $129,600 to $162,000 based on a 37.5 hour work week. Actual offered salary will depend on the successful candidate's qualifications and experience, as well as market conditions for the role, and internal equity.

Westland also offers a competitive annual short-term incentive program that enables employees to share in the rewards of the business and emphasizes the measures that are key to our success.

Reason for Vacancy: This posting is to fill a current vacancy on our team.

Interested in learning more?

Why you'll love Westland:

• An open, flexible and welcoming workplace
• Plenty of opportunities to grow and learn
• Autonomy to drive your own success
• Be part of our inclusive culture, alongside an extraordinarily talented community with a wide variety of backgrounds
• A total rewards program that supports your financial, physical, and mental wellbeing
• Flexible paid Values Days to celebrate days important to you
• Paid Volunteer Days for employees as part of Amplifying Communities, supporting causes that matter most to our people and clients

Why we'll love you:

• 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)
• CIP, CAIB, or CRM designation considered an asset
• High degree of professional integrity with a commitment to delivering exceptional client experiences
• Entrepreneurial mindset with strong business acumen and a growth-oriented approach

Once here, you'll:

• 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

As part of our commitment to transparency, we want to let you know that while our recruitment system includes AI capabilities, these are never used to screen, evaluate, or select candidates. The only AI functionality that Westland uses is for transcribing notes during candidate calls, and this occurs with your consent. These tools aren't used to make any hiring decisions throughout our recruitment process.

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Want to get to know each other better? Send your resume our way.