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For Companies At a Glance
- Tasks: Manage and grow client accounts while providing exceptional service to trucking companies.
- Company: Join Westland Insurance, a company dedicated to growth and community care.
- Benefits: Enjoy flexible work options, professional development support, and wellness programs.
- Why this job: Be part of an inclusive culture that values your contributions and offers growth opportunities.
- Qualifications: 5+ years in sales with experience in managing fleet clients and a valid LLQP license.
- Other info: This role allows for hybrid or fully remote work, promoting a balanced lifestyle.
The predicted salary is between 36000 - 60000 £ per year.
Posted Thursday, July 31, 2025 at 4:00 AM
We’re searching for an Account Executive, Fleet. Are you searching for new possibilities?
Westland Insurance Group Ltd has an exciting opportunity for an Account Executive, Fleet 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 commercial 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, Fleet, you’ll redefine the way commercial 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:
- 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.
- An active LLQP license
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.
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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
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Account Executive, Fleet employer: Westland Insurance Group Ltd.
Contact Detail:
Westland Insurance Group Ltd. Recruiting Team
StudySmarter Expert Advice 🤫
We think this is how you could land Account Executive, Fleet
✨Tip Number 1
Network actively within the trucking and insurance industries. Attend relevant events, seminars, and conferences to meet potential clients and industry peers. Building relationships in person can significantly enhance your chances of landing this role.
✨Tip Number 2
Familiarise yourself with Westland Insurance's values and culture. Understanding their commitment to community and client service will help you align your approach during interviews and discussions, showcasing that you're a great fit for their team.
✨Tip Number 3
Prepare to discuss your previous successes in managing and growing a book of business. Be ready to share specific examples of how you've built relationships with clients, particularly in the fleet sector, to demonstrate your capability and results-driven mindset.
✨Tip Number 4
Stay updated on industry trends and challenges facing the trucking sector. Being knowledgeable about current issues will not only help you in conversations but also position you as a valuable advisor to potential clients, which is crucial for this role.
We think you need these skills to ace Account Executive, Fleet
Some tips for your application 🫡
Tailor Your CV: Make sure to customise your CV to highlight your experience in managing and growing a book of business, especially in the Accident & Sickness sector. Emphasise any relevant achievements that demonstrate your sales mindset and ability to build relationships with clients.
Craft a Compelling Cover Letter: Write a cover letter that showcases your passion for client service and your proactive approach to identifying new business opportunities. Mention specific examples of how you've successfully managed large accounts or expanded your portfolio in previous roles.
Highlight Relevant Skills: In your application, clearly outline your strong communication and interpersonal skills. Provide examples of how these skills have helped you in networking at events or negotiating terms for clients, as this is crucial for the Account Executive role.
Showcase Your Industry Knowledge: Demonstrate your understanding of the insurance industry, particularly in relation to fleet clients. Mention any relevant certifications, such as your active LLQP license, and express your enthusiasm for continuous learning and professional development.
How to prepare for a job interview at Westland Insurance Group Ltd.
✨Showcase Your Sales Experience
Be prepared to discuss your proven track record in managing and growing a book of business. Highlight specific examples where you've successfully sold Accident & Sickness products and how you’ve built relationships with fleet clients.
✨Demonstrate Client-Centric Mindset
Since the role focuses on exceptional client service, share instances where you've gone above and beyond for clients. Emphasise your ability to provide proactive solutions and maintain strong relationships with established accounts.
✨Prepare for Networking Questions
Expect questions about your networking strategies. Be ready to explain how you identify and seize new business opportunities, and discuss your experience attending industry events to expand your connections.
✨Exhibit Strong Communication Skills
Communication is key in this role. Practice articulating your thoughts clearly and confidently. Prepare to discuss how your interpersonal skills have helped you in previous roles, especially in negotiating terms and conditions for clients.
