Director, Commercial Transportation

Job Description

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.

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

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

You belong here 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. Every day, Westland proves that building a great business means taking care of communities, clients, and each other with equal commitment. You will be supported and respected for who you are and for the voice you add to the conversation. At Westland, you will feel the power of community. 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. 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.

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