Director, Health

Director, Health & Life - Westland Benefits

Job Description

Posted Thursday, October 16, 2025 at 7:00 AM

We’re searching for aDirector, Health & Life – Westland Benefits.Are you searching for new possibilities?

Westland Insurance Group Ltd. is growing and has a new opportunity for aDirector, Health and Life This is ahybrid role based out of the office in Burlington, ON. This strategic leadership position is responsible for driving growth, client retention, and operational excellence in the Group Health and Life Insurance spaces. The region this role oversees is Ontario . If you’re passionate about building high-performing teams and delivering exceptional client experiences, you’ll love working for Westland

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.

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 communities, clients, and each other with equal commitment. As we continue to open new doors, we're inviting amazing people like you to join us.

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 10+ years of progressive leadership experience in group benefits, health & life insurance, or related fields
- You have a proven ability to manage client relationships and deliver strategic solutions
- You understand regional market dynamics and have strong communication, presentation, and problem-solving skills
- You’re proficient in Microsoft Office and CRM systems
- You’re licensed under applicable provincial insurance regulations
- Industry designations such as CEBS, GBA, or similar are considered assets
- You demonstrate accountability, collaboration, expertise, resiliency, and a client-first mindset

Once here, you'll:

- Translate corporate strategy into actionable departmental plans across Sales, Underwriting, Client Account Management, and Customer Service.
- Lead and develop a team of managers, fostering alignment, accountability, and collaboration.
- Drive operational excellence and integration across departments to deliver seamless client experiences.
- Lead the development and execution of growth strategies, broker engagement plans, and client acquisition initiatives, while continuously monitoring market trends and competitive dynamics to inform sales tactics and optimize product positioning.
- Oversee underwriting governance and risk management.
- Champion client experience and retention strategies.
- Build leadership capacity and promote a high-performance, inclusive culture.
- Act as a key advisor to the Vice President, contributing to long-term planning, product innovation, succession planning, and market positioning.

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Join us and be part of a team that’s shaping the future of Group Health and Life Insurance at Westland.

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

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

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