Job Description

We’re searching for a Vice President, Commercial Lines - Saskatchewan & Manitoba. Are you searching for new possibilities?
Westland Insurance Group Ltd. is growing, and we’re looking for a dynamic commercial leader to help shape the future of our business across Saskatchewan and Manitoba as Vice President, Commercial Lines. In this highly visible leadership role, you’ll drive profitable growth, lead high-performing teams, strengthen key carrier and client relationships, and play a critical role in executing Westland’s commercial strategy across both provinces.
This is an opportunity to make a significant impact within one of Canada’s fastest-growing insurance brokerages - leading through growth, supporting acquisition integration, developing future leaders, and helping elevate our commercial business to the next level. If you’re a strategic and relationship-driven leader who thrives in a fast-paced, entrepreneurial environment, this is your chance to help shape the future of Commercial Lines at Westland.

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 clients, communities, and each other with equal commitment. As we continue to open new doors, we're inviting amazing people like you to join us.
As the Vice President, Commercial Lines - Saskatchewan & Manitoba, you’ll drive profitable commercial growth, represent Westland to clients and partners, and lead the execution of our Commercial business plan. With your strong business acumen, leadership skills, and technical expertise, you will be instrumental in achieving our commercial goals across both regions.
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 of people with a wide variety of backgrounds
• A total rewards program that takes care of your financial, physical, and mental health
• Flexible paid Values Days to celebrate days important to you
• Paid Volunteer Days for employees as part of Amplifying Communities, a program to support causes that matter most to our employees and clients
Why we’ll love you
• You bring a minimum of 10 years of commercial lines experience, complemented by 7+ years in progressive leadership roles.
• You have a demonstrated track record of driving organizational success through strong sales, service, and operational leadership.
• You are skilled at building, coaching, and leading high-performing teams in a fast-paced environment.
• You excel at collaborating with cross-functional business leaders and bring strong strategic thinking and problem-solving capabilities.
• You bring strong business acumen, sound judgment, and an entrepreneurial mindset.
• Your communication and interpersonal abilities are exceptional, supported by a high degree of personal and professional integrity.
• You are passionate about mentoring talent and developing future leaders.
• Experience supporting mergers and acquisitions is considered an asset.
• You hold a CIP designation and are eligible for insurance licensing.
• A Level 3 General Insurance License, or progress toward obtaining one, is considered an asset.
• Additional industry designations such as CAIB, CRM, or FCIP are considered an asset.
• Post-secondary education in Business Administration or a related discipline is also considered an asset.
Once here you’ll
• Lead and inspire a team of commercial lines leaders across multiple offices, driving high performance, accountability, and consistent execution of regional objectives.
• Own the commercial strategy for the region, including business development, sales execution, client service, and the development and delivery of the annual business plan.
• Build and maintain strong relationships with regional and national markets, external carrier partners, and Westland’s largest and most strategic clients.
• Oversee key growth and portfolio management processes, including renewal stewardship, portfolio reviews, and escalation frameworks, ensuring disciplined execution and sustained profitability.
• Lead acquisition integration efforts, ensuring seamless transition of talent, clients, and revenue while maintaining strong engagement and retention outcomes.
• Develop and grow internal talent pipelines by coaching leaders, identifying future successors, and fostering a high-performance culture across the region.
• Collaborate with senior leaders across the organization to deliver enterprise-wide initiatives and monitor key performance metrics, driving continuous improvement and performance accountability.
• Represent Westland externally by staying informed on industry trends, maintaining strong market presence, and participating in relevant professional associations.
• Travel as required to support leadership effectiveness and regional priorities.
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Want to get to know each other better? Send your resume our way.
You belong here.

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