Account Executive, Benefits Insurance

Posted Wednesday, May 13, 2026 at 7:00 AM We’re searching for an Account Executive, Benefits 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 insurance advisor to foster valued relationships with our clients. Do you have your LLQP license and experience working in the Benefits (Accident and Sickness) field of Insurance? If so, you will love working for Westland! Expected Compensation: The expected hiring range for this role is $75,000 - $87,500 based on a 37.5 -hour work we ek. Actual offered salary will depend on the successful candidate’s qualifications and experience, as well as market conditions for the role, and internal equity. Westland also offers a competitive commission for this role. Reason for Vacancy: This posting is to fill a current vacancy on our team. 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. 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. #LI-SS1 #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 [email protected]