Vice President, Commercial Insurance - Saskatchewan & Manitoba

Talent Acquisition Team at Westland Insurance. Text reply only. • Regina, SK

7d • Hybrid

About The Position

Westland Insurance Group Ltd. is seeking a dynamic commercial leader to shape the future of its business across Saskatchewan and Manitoba as Vice President, Commercial Lines. This leadership role involves driving profitable growth, leading high-performing teams, strengthening key carrier and client relationships, and executing Westland’s commercial strategy. The position offers an opportunity to make a significant impact within a fast-growing insurance brokerage by leading through growth, supporting acquisition integration, developing future leaders, and elevating the commercial business. The ideal candidate is a strategic, relationship-driven leader who thrives in a fast-paced, entrepreneurial environment.

Requirements

• A minimum of 10 years of commercial lines experience.
• 7+ years in progressive leadership roles.
• Demonstrated track record of driving organizational success through strong sales, service, and operational leadership.
• Skilled at building, coaching, and leading high-performing teams in a fast-paced environment.
• Ability to collaborate with cross-functional business leaders.
• Strong strategic thinking and problem-solving capabilities.
• Strong business acumen, sound judgment, and an entrepreneurial mindset.
• Exceptional communication and interpersonal abilities.
• High degree of personal and professional integrity.
• Passion for mentoring talent and developing future leaders.
• Hold a CIP designation.
• Eligible for insurance licensing.

Nice To Haves

• Experience supporting mergers and acquisitions.
• A Level 3 General Insurance License, or progress toward obtaining one.
• Additional industry designations such as CAIB, CRM, or FCIP.
• Post-secondary education in Business Administration or a related discipline.

Responsibilities

• 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.

Benefits

• An open, flexible and welcoming workplace
• Plenty of opportunities to grow and learn
• Autonomy to drive your own success
• Inclusive culture
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: Associate degree