Director, National Personal Sales - Digital Sales
About The Position
Westland Insurance Group Ltd. has an exciting opportunity for a Director, National Personal Lines - Digital Sales to be based out of our Surrey, Calgary, or GTA office. This is a hybrid position. The Director is responsible for leading and overseeing Westland’s Personal Lines Digital Sales teams across Canada. This role will lead regional sales leaders, drive digital channel performance, and execute growth strategies that support national business objectives. This role drives national digital sales strategy, operational excellence, channel effectiveness, and business growth, ensuring consistent performance and an exceptional client experience across all regions. The Director is responsible for overseeing the national Digital Sales team's performance and business development activities, ensuring sales leaders and teams consistently execute established processes and achieve business objectives. This role is accountable for team member engagement, development, performance, and recruitment.
Requirements
- 5+ years of leadership experience, including proven success leading multi-regional or national sales teams within insurance or a related industry
- Demonstrated underwriting expertise and market experience
- Extensive experience leading technology-enabled sales transformation and digital growth initiatives
- Proven ability to build and leverage strategic partnerships and professional networks to drive business growth
- Demonstrated expertise in designing, optimizing, and scaling sales workflows and operational processes
- Established track record of leading leaders, driving business results, and executing organizational objectives
- High level of personal and professional integrity with exceptional communication and interpersonal skills
- Demonstrated ability to collaborate effectively with cross-functional business leaders
- Ability to lead through complex and ambiguous business challenges
- Level 2 General Insurance License (or equivalent)
- Willingness to travel nationally as required
Nice To Haves
- Industry designation preferred (CAIB, CIP, CRM, FCIP)
Responsibilities
- Lead and develop Personal Lines Digital Sales teams nationwide, providing direction through regional leadership and driving consistent business results
- Oversee digital sales strategy, channel performance, and business development initiatives across Canada
- Ensure effective execution of sales processes while maintaining governance, compliance, and alignment with organizational standards
- Establish high-performance expectations and a culture of accountability through coaching, development, and performance management
- Partner with Marketing, Underwriting, and other business leaders to execute strategic corporate initiatives
- Monitor and report on national sales performance, key metrics, and market trends, leveraging data-driven insights to drive continuous improvement
- Develop and maintain a robust professional network that supports growth, market expansion, and strategic partnerships
- Support regional leaders in resolving complex business and operational challenges
- Identify and develop high-potential talent to strengthen leadership succession and organizational capability
- Represent the organization through industry associations, partnerships, and events while maintaining strong industry expertise
- Travel nationally as required to support teams, strengthen alignment, and advance digital sales priorities
Benefits
- Competitive annual short-term incentive program
- Financial assistance is available for approved work-related training/development courses leading to certification
- Programs that offer professional development, including seminars and conferences
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
