Director, Commercial Transportation

Join to apply for the Director, Commercial Transportation role at Westland Insurance Group Ltd. 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. 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 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. We are an inclusive organization that values diversity, champions equity and diversity, and creates safe welcoming spaces where everyone has a voice and is free to be themselves. Send your resume to . If you require a disability‑related accommodation to participate in the recruitment process, please contact the recruitment team by email at . Job Details Seniority level: Director Employment type: Full‑time Job function: Business Development and Sales Industry: Insurance Location: Toronto, ON Position type: Hybrid #J-18808-Ljbffr