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Westland Insurance Group LtdWL

Account Executive, Benefits Insurance

Westland Insurance is one of Canada's largest and fastest-growing independent insurance brokers, providing personal, commercial, and employee benefits insurance solutions.

Westland Insurance Group Ltd

Employee count: 1001-5000

Canada only

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We’re searching for an Account Executive, Fleet Insurance. Are you searching for new possibilities?

Westland Insurance Group Ltd has an exciting opportunity for an Account Executive, Benefits Insurance based in Mississauga, ON or the Greater Toronto Area. This role can be either hybrid or fully remote. You will be responsible for maintaining and growing a book of business and acting as an advisor to foster valued relationships with our clients. Are you a results-driven person who also loves providing exceptional client service? If so, you will 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 clients, communities, and each other with equal commitment. As we continue to open new doors, we're inviting amazing people like you to join us.

As an Account Executive, Benefits Insurance, you’ll redefine the way clients buy insurance by delivering innovative solutions to help achieve Westland’s growth strategy.

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:

  • An active LLQP license
  • You have a proven track record of managing and growing a book of business, with 5+ years of experience selling Accident & Sickness products and at least 1 year managing fleet clients.
  • You thrive with a sales mindset and are motivated to expand your portfolio by building relationships with new trucking clients.
  • You are proactive and independent, with a strong ability to identify and seize new business opportunities.
  • You’re a customer service champion who can deliver an exceptional experience while servicing large, established accounts like trucking companies.
  • You own a vehicle and have a valid driver’s license, as this role requires travel to clients within the Greater Toronto Area and Southwestern Ontario.
  • You have strong sales and business acumen, and you’re confident in networking at events, seminars, and industry functions to expand your connections.
  • You have excellent communication and interpersonal skills, with a sharp eye for attention to detail and accuracy.

Once here, you'll:

  • Manage large accounts by providing superior service to established trucking clients, ensuring all their needs are met with proactive solutions and attention to detail.
  • Drive new business by seeking out and developing relationships with potential trucking clients, attending networking events, and generating leads to expand your book of business.
  • Prepare marketing submissions and proposals, negotiating favorable terms and conditions on behalf of your clients.
  • Be on the road regularly, traveling to client sites for in-person visits, building lasting relationships across Ontario.

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 talentacquisition@westlandinsurance.ca

About the job

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Posted on

Job type

Full Time

Experience level

Mid-level

Location requirements

Hiring timezones

Canada +/- 0 hours

About Westland Insurance Group Ltd

Learn more about Westland Insurance Group Ltd and their company culture.

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At Westland Insurance, we are at the forefront of revolutionizing the insurance brokerage industry through significant investments in technology and a forward-thinking approach to client service. Our commitment to innovation is demonstrated by our adoption of cutting-edge broker management systems like Acturis and the comprehensive Applied Digital Brokerage suite, which includes Applied Epic, Cloud, CSR24, Mobile, Analytics, and Rating Services. This technological infrastructure empowers our expert advisors to deliver tailored insurance solutions with unparalleled efficiency and accuracy. We are continuously exploring and integrating advanced technologies, including artificial intelligence and data analytics, to enhance our service delivery, streamline processes, and provide our clients with a seamless, modern insurance experience. Our digital platform, Westland Express, which integrates with property management software like Yardi Voyager and HappyCo, exemplifies our dedication to providing accessible and convenient online insurance solutions.

Founded in 1980, Westland Insurance has grown from a single family-owned brokerage into one of Canada's largest and most trusted independent insurance brokers. This growth is fueled by our relentless pursuit of excellence and our strategic focus on digital transformation. We are not just an insurance provider; we are a technology-driven partner committed to protecting individuals, businesses, and communities across Canada. Our recent appointment of a Chief Information Officer underscores our dedication to scaling our technology infrastructure and driving data enablement and AI innovation. By harnessing the power of technology, we are not only simplifying the insurance process for our clients but also equipping our team of over 3,000 professionals with the tools they need to provide expert, advisory-based services across a wide range of insurance segments. Our vision is to be Canada's favorite insurance broker, and we believe that our investment in technology and innovation is the key to achieving that goal.

Employee benefits

Learn about the employee benefits and perks provided at Westland Insurance Group Ltd.

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Dayforce Wallet™

A modern, flexible on-demand pay program.

RRSP matching

Westland offers RRSP matching for its employees.

Insurance discounts

Employees receive discounts on insurance products.

Retirement and savings plans

The company provides retirement and savings plans.

View Westland Insurance Group Ltd's employee benefits
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Westland Insurance Group Ltd

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Westland Insurance Group Ltd hiring Account Executive, Benefits Insurance • Remote (Work from Home) | Himalayas