Director, Commercial Insurance (Winnipeg)

Director, Commercial Insurance (Winnipeg)

25 Aug
|
Westland Insurance Group
|
Winnipeg

25 Aug

Westland Insurance Group

Winnipeg

Edmonton Regional, AB, 17203 103 Ave NW #100, Edmonton, Alberta, Canada

Job Description Posted Friday, August 21, 2026 at 7:00 AM

W e’re searching for a Director, Commercial Insurance. Are you searching for new possibilities?

Westland Insurance Group Ltd. is growing, and we’re looking for a dynamic commercial insurance leader to elevate our Middle Market segment as Director, Commercial Insurance . This is a leadership role responsible for driving growth, strengthening client relationships, and empowering a high-performing team of Account Executives. This is a

hybrid

role based in

Edmonton, AB

with travel as required.

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.

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 and development programs, including courses, seminars, and conferences that support your professional growth.

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.

Do you thrive on building high-performing sales and service teams? Are you passionate about developing commercial insurance professionals, strengthening market relationships, and driving disciplined growth strategies? If so, join our collaborative Commercial leadership team at Westland Insurance - where expertise, relationships, and client experience come first.

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:

Minimum of 5 years in commercial lines with 3-5 years of leadership experience

Level 3 General Insurance License required. Industry designations (CAIB, CIP, CRM, or FCIP) preferred.

Proven experience coaching, developing, and leading high-performing teams

Strong track record of meeting business results through strategic leadership and disciplined execution

Deep commercial marketplace knowledge with the ability to guide Account Executives on marketing strategy, portfolio management, and retention best practices

Strong communication, interpersonal, and relationship-building skills

Experience collaborating with cross-functional business partners and solving complex business problems

High level of professional integrity and a commitment to delivering exceptional client experiences

Entrepreneurial mindset with strong business acumen and a growth-oriented approach

Once here, you'll:

Lead and coach a team of Commercial Account Executives to drive growth, retention, and strong process execution

Partner with the Commercial Servicing Team to ensure seamless client service

Collaborate with the Marketing team to deliver high-quality market submissions

Ensure adherence to key growth processes, including Portfolio Reviews, Renewal Stewardship,



the Jeopardy Process and Strategic Account Reviews

Oversee team business development and operational performance, including process execution, client service, and employee attraction, development, and retention

Engage directly with clients, prospects, and carrier partners when additional support is required

Set individual goals, provide coaching, and hold team members accountable for results

Collaborate with cross-functional leaders across Personal Lines, People & Performance, Finance, and IT to deliver on corporate initiatives

Monitor and act on performance metrics to support continuous improvement

Maintain solid industry knowledge and participate actively in regional insurance associations and carrier networks

Travel as needed to support clients, markets, and team members

#LI-AA1

#LI-Hybrid

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

[email protected]

Edmonton Regional, AB, 17203 103 Ave NW #100, Edmonton, Alberta, Canada

#J-18808-Ljbffr

📌 Director, Commercial Insurance (Winnipeg)
🏢 Westland Insurance Group
📍 Winnipeg

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