Outside Sales Representative

Posted 26 May 2026
LocationWinnipeg
Job type Permanent
DivisionExecutive & Professional Search
Ref #22894
Join a high-performance outside sales team as an Outside Sales Representative responsible for driving new business within an assigned territory. This role is focused on continuous prospecting through cold calling, networking, and direct engagement, while managing a structured pipeline, tracking activity through CRM systems, and maintaining consistent progress reporting. You will also deliver presentations, close new business deals, and stay informed on market trends and competitive activity to support ongoing territory growth and business development.

WHY WORK WITH THIS COMPANY? 
This is an extremely established Manitoba-based organization with a long-standing reputation and a strong, high-performance sales culture. Built on deep local roots and a legacy of growth, it offers an environment where effort, drive, and results are directly rewarded. The role sits within a highly motivated outside sales team focused on expansion and performance, offering uncapped commission and the ability to meaningfully control earning potential. It is well suited for a driven individual looking for more than just a position, but a long-term career path within a competitive, results-oriented environment.

YOUR RESPONSIBILITIES
*Generate and maintain a pipeline of new business opportunities and maintain a pipeline within an assigned territory.
*Consistently meet and exceed performance objectives by conducting proactive outreach activities including prospecting, cold calling, networking, email communication, and in-person engagement efforts.
*Develop and manage a strategic sales pipeline by prioritizing opportunities, monitoring progress, and maintaining an organized approach to territory planning and business development activities.
*Accurately track sales activity, opportunity development, and performance metrics using CRM platforms and internal reporting systems while providing regular updates to leadership teams.
*Deliver professional presentations and effectively communicate service offerings while managing negotiations, agreements, and partnership discussions with prospective and existing business contacts.
*Stay informed on industry developments, market trends, and competitive activity to support strategic positioning and continued business growth.

WHAT WE’RE LOOKING FOR 
*Proven B2B sales experience with a strong focus on business development, relationship building, and new account acquisition.
*Driven “hunter” mentality with the ability to proactively identify opportunities and generate new business growth.
*Self-motivated professional with strong relationship-building skills and a track record of achieving sales results.
*Excellent written and verbal communication skills, with confidence presenting to and engaging with stakeholders at all levels.
*Collaborative and adaptable team player who can also work independently in a fast-paced environment.
*Proficient in CRM platforms and Microsoft Office applications, including Outlook, Word, Excel, and PowerPoint.
*Results-oriented mindset with a focus on exceeding targets and driving revenue growth.
*Background in customer service, account management, or client relationship management considered an asset.
*Valid driver’s license and reliable vehicle required, with the ability to travel throughout Winnipeg and surrounding areas.