Insurance, Insurance Sales, Insurance Agent

Commercial Account Executive - Crossroads Insurance

Province:
Winnipeg, Manitoba
Position:
Commercial Account Executive

Posted:
February 4, 2026

What You’ll Be Doing:

• Building strong, lasting relationships with commercial clients (because trust is everything).
• Supporting your clients with regular account reviews (min annual), helpful advice, and exceptional service in all situations.
• Identifying opportunities to cross-sell, up-sell, and uncover hidden needs
• Guiding clients through the claims process with care and professionalism.
• Developing and pursuing new business (yes, we know “cold-calling” isn’t glamorous, but you’re confident and great at starting conversations) and are confident in doing so.
• Collaborating with our experienced marketing team to craft competitive insurance solutions and updating underwriting information as required.
• Continuously expanding your knowledge of the industry, clients, and products.

What You Bring to the Table:

• At least 3 years of experience in commercial insurance.
• Min. Level 2 General Insurance License (Life & A&S license is a nice-to-have).
• Superior sales and customer service skills with a desire to build relationships, while maintaining integrity at the forefront
• An entrepreneurial mindset and a passion for helping businesses protect what they’ve built.
• A knack for building trust and finding solutions.
• Top-notch communication and organization skills.
• Strong attention to detail and sound work ethic
• A self-starter attitude with a willingness to develop new business.
• Comfort with detailed underwriting info and supporting our marketing team when needed.

Why You'll Love Working Here:

• A flexible hybrid work environment that supports your lifestyle.
• A competitive compensation structure, with a strong commission arrangement.
• Sponsored licensing and continuing education, we invest in your growth.
• Company-matching RRSP plan (your future self will thank you).
• Comprehensive group benefits to keep you feeling your best.
• An experienced marketing department that’s got your back when it comes to quoting and placement.
• Access to a wide range of markets; we can insure just about anything!
• A collaborative, people-first culture that encourages innovation and celebrates success.
• Have a book of business? Great! Don’t have one yet? No problem. We’re flexible and will tailor a compensation model that works for you.

Ready to take your insurance career to the next level? Let’s talk.
Send your resume in confidence to TJ McRedmond at
tjmcr, Ph:

Grow with a team that feels like home.
Are you a relationship-builder who thrives on making a difference for your clients? Do you love the idea of working with a down-to-earth team that blends professionalism with personality? If so, we think you'll love it here at Crossroads Insurance.

We’re looking for a Commercial Account Executive to join our growing team. If you’re driven and experienced in Commercial Lines (with a side of Personal Lines or Life insurance knowledge; that’s a bonus!), and you’re ready to work somewhere that values relationships just as much as results, keep reading.

For over 50 years, Crossroads has been more than a brokerage. We’re a trusted partner to our clients and a supportive, team-first workplace. We’re passionate about what we do and who we do it with. We believe in blending innovation with heart, and we’re proud to offer a work environment that’s as rewarding as it is welcoming.