As of November 7, 2026, Jobsy lists 2 b2b sales representative jobs in Winnipeg, MB. The most active employers are GroupHEALTH Benefits, GroupStrength Benefits Direct and AI Acquisition. Skills often requested: sales, communication skills, cold calling and llqp.
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1+ YOECandidates need 1-2 years of B2B sales experience, strong written and verbal communication, cold calling and lead generation skills, and comfort with technology and CRM systems. Insurance or group benefits experience and French are assets; the LLQP licence is obtained during onboarding.
GroupStrength Benefits Direct: provides small to mid-sized Canadian organizations with comprehensive yet affordable employee group benefits plans.
1+ YOECandidates need 1-2 years of B2B sales experience, strong written and verbal communication, cold calling and lead generation skills, and a self-starting drive. Insurance or group benefits experience, CRM familiarity and French are assets.
CRM system, GroupHEALTH tools
Common questions
Who is hiring b2b sales representatives?
GroupHEALTH Benefits (3), GroupStrength Benefits Direct (3), AI Acquisition (1), Altis (1) and G&A Robot (1).
What skills do b2b sales representative jobs ask for?
Postings most often mention sales, communication skills, cold calling, llqp, bilingualism, decision making, onboarding and impact.