Director, Commercial Transportation

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.

Westland is committed to continuous learning where employees can grow their potential and write the stories of their careers. Financial assistance is available for approved work-related training and development programs, including courses, seminars, and conferences that support your professional growth.

Discover what’s possible, with Westland.

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. As we continue to open new doors, we're inviting amazing people like you to join us.

Do you thrive on leading advisory teams supporting complex commercial transportation risks? Are you passionate about strengthening client relationships, navigating regulatory environments, and building innovative insurance solutions in a fast-moving sector? If so, join our collaborative Commercial leadership team at Westland Insurance—where expertise, relationships, and exceptional service come first.

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.