Director, National Personal Lines - Digital Sales

Westland Insurance Group Ltd.; Surrey; Hybrid; CAD 105,000 - 131,000; Full time

Benefits offered by this job

Flexible workplace

Growth opportunities

Autonomy

Inclusive culture

Total rewards

Values Days

Volunteer days

Job summary

Westland Insurance Group Ltd. is seeking a Director of National Personal Lines - Digital Sales to lead digital sales across Canada.

The role is hybrid and based out of Surrey, Calgary, or the Greater Toronto Area, with a focus on growth, channel performance, and delivering exceptional client experiences. The ideal candidate has 5+ years of leadership in national sales, experience driving technology-enabled sales transformations, and a track record of building strategic partnerships while

Qualifications

• 5+ years leading multi-regional or national sales teams in insurance or related industries.
• Experience leading technology-enabled sales transformation and digital growth initiatives.
• Proven ability to build and leverage strategic partnerships and networks to drive growth.
• Designing, optimizing, and scaling sales workflows and operational processes.
• Proven track record of leading leaders, driving results, and aligning with objectives.
• High integrity with strong communication and interpersonal skills.
• Willingness to travel nationally as required.

Responsibilities

• Lead Personal Lines Digital Sales teams nationwide through regional leadership.
• Oversee digital sales strategy, channel performance, and business development across Canada.
• Ensure execution of sales processes with governance and compliance.
• Coach and develop leaders to establish accountability and high performance.
• Partner with Marketing, Underwriting and other leaders on strategic initiatives.
• Monitor national sales performance with data-driven insights for improvement.
• Develop a robust professional network to support growth and partnerships.
• Support regional leaders in solving complex business and operational challenges.
• Identify top talent to strengthen leadership succession and capability.
• Represent the company through industry associations and events.

Skills

Leadership experience

Digital sales

Insurance knowledge

Strategic partnerships

Cross-functional collaboration

Travel willingness

Education

Level 2 General Insurance License

Industry designation preferred

Job description

Director, National Personal Lines - Digital Sales

We’re searching for a Director, National Personal Lines - Digital Sales. Are you searching for new possibilities?

Westland Insurance Group Ltd. has an exciting opportunity for a Director, National Personal Lines - Digital Sales. This hybrid role can be based out of one of our major office locations, including Surrey, BC, Calgary, AB, or the Greater Toronto Area, offering the opportunity to collaborate with colleagues and partners across the country.

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.

Compensation

Expected Compensation: The expected hiring range for this role is $105,000 to $131,000 based on a 35‑hour work week. Actual offered salary will depend on the successful candidate’s qualifications, experience, and market conditions for the role.

Westland also offers a competitive annual short‑term incentive program that enables employees to share in the rewards of the business and emphasizes the measures that are key to our success.

Reason for Vacancy

This is a new opportunity within our team.

Learning & Development

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/development courses leading to certification, and programs that offer professional development, including seminars and conferences.

Benefits

• 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

Qualifications

• 5+ years of leadership experience, including proven success leading multi‑regional or national sales teams within insurance or a related industry
• 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)
• Industry designation preferred (CAIB, CIP, CRM, FCIP)
• Willingness to travel nationally as required

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

As part of our commitment to transparency, we want to let you know that while our recruitment system includes AI capabilities, these are never used to screen, evaluate, or select candidates. The only AI functionality that Westland uses is for transcribing notes during candidate calls, and this occurs with your consent. These tools aren't used to make any hiring decisions throughout our recruitment process.

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

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 [e-mail].