Job Description

We're searching for a Director, Commercial Middle Market. 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 Middle Market (Hybrid). This is a leadership role responsible for driving growth, strengthening client relationships, and empowering a high-performing team of Account Executives. This position is based out of our Thunder Bay, Ontario office, with travel as required.



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 strong industry knowledge and participate actively in regional insurance associations and carrier networks Travel as needed to support clients, markets, and team members

#LI-SD1

#LI-Hybrid



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