Outside Sales Executive

Job Title: Outside Sales Executive – InsuranceLocation: Welland, ON (Hybrid)Employment Type: Full-TimeIndustry Focus: Personal Lines Insurance (Commercial Lines growth opportunity)

Who We’re Looking For:Are you a natural connector with a drive to succeed? Do you thrive in a sales-focused environment where results speak for themselves? We’re looking for a motivated, community-connected Outside Sales Executive to grow our client base in Welland and surrounding areas. This is a hunter-style, prospecting role — ideal for a recent college or university graduate (2–3 years post-graduation) with some experience in a customer-facing environment who is ready to build a rewarding career in insurance sales.

This is a proactive sales role — you will not be given leads to quote. Success in this role comes from your ability to find, create, and close new business opportunities through relationship building and prospecting.

Comprehensive training will be provided to help you succeed, including product knowledge, sales strategy, and support for licensing if required.

Compensation & Benefits:

• Base Salary: $50,000 – $55,000 annually

• Tiered Commission Structure: Competitive, performance-based commissions with uncapped earning potential

• Group Benefits Package

• Support for licensing and professional development

• Hybrid work model for flexibility and autonomy

• Ongoing training and mentorship to ensure your long-term success

Key Responsibilities:

• Proactively identify and generate new business opportunities through community engagement, cold outreach, and networking.

• Build and maintain strong relationships within the Welland community to create a sustainable pipeline of referrals and leads.

• Conduct prospect meetings to assess insurance needs and present tailored personal lines insurance solutions (with opportunity to expand into commercial lines as your experience grows).

• Maintain accurate and timely documentation of client interactions using CRM tools.

• Collaborate with internal underwriting and service teams to deliver a seamless client experience.

• Stay informed on market trends, product offerings, and regulatory requirements.

What You Bring to the Role:

• 2–3 years of post-graduate work experience in a customer-facing, sales, or relationship-building role.

• Demonstrated ability to network, prospect, and build business independently.

• Deep familiarity or active involvement within the Welland community; ability to leverage Centers of Influence (COIs).

• Resilient, self-motivated, and highly organized — thrives in a base-plus-commission, entrepreneurial environment.

• Passion for helping clients and building long-term relationships.

• Strong communication, presentation, and interpersonal skills.

• Comfort using digital tools, CRMs, and virtual communication platforms.

• Insurance industry experience or RIBO license is a strong asset, but not required. Training and licensing support will be provided.

Why Join Us?

• Stable base salary with significant commission upside

• Full group benefits and ongoing professional development

• Paid training to set you up for success in your role

• Hybrid flexibility – combine in-office collaboration with in-community outreach

• Be part of a trusted and growing organization that values initiative and ambition

• Opportunity to build the book of business and shape your career path

This is your opportunity to step into a dynamic sales role where your income and growth are truly in your hands. If you’re ready to hustle, connect, and succeed — we want to hear from you.

Apply today and start building your future in insurance.