B2B Employee Benefits Sales Representative
Location Winnipeg, On-Site
Job type: Full time, Permanent
About GroupStrength
At GroupStrength, we’re shaking up the Canadian group benefits industry with bold, direct-to-client solutions that cut through the noise; saving clients time, money, and frustration.
Our people are what set us apart. From sales to support, we’ve built a team that’s hungry, innovative, and genuinely excited about the difference we’re making. We work hard, celebrate wins, and support each other every step of the way. It’s the kind of environment where we all thrive and where our people choose to stay because they feel valued, challenged, and part of something bigger.
At GroupStrength you will grow your career and be part of a team that actually loves what they do.
YOUR ROLE
As a B2B Sales Representative, you will engage with prospects nationwide through phone and video meetings, showcasing the unparalleled GroupHEALTH employee benefits solutions. Supported by cutting-edge tools and expert guidance, you'll be part of a team that has added nearly 2,000 clients during the pandemic—demonstrating our ability to meet the evolving needs of Canadian employers and employees. Your exceptional sales skills will be key in exceeding quotas and helping businesses enhance their benefits offerings.
WHAT TO EXPECT
Your onboarding journey at GroupStrength is designed to set you up for success:
YOUR IMPACT
THIS IS YOU
YOUR COMPENSATION
On-Target earning projections are a combination of a starting salary of $45,000 plus uncapped commissions, bonuses and a capped increasing base salary as metrics are achieved.
WHAT YOU’LL GET
In addition to a competitive base salary, uncapped commission, and benefits, you’ll enjoy:
We also offer comprehensive health and wellness benefits, including employee wellness activities, and we’ll reimburse your LLQP Designation upon completion!
WHY YOU’LL LOVE WORKING FOR GROUPSTRENGTH
We’re committed to your professional growth, offering promotion opportunities, career development paths, and various learning and development programs. Our robust health and wellness benefits allow you to customize your plan to fit your needs. Plus, with virtual company-wide events, team socials, and more, we foster a collaborative and engaging work environment.
Join our forward-thinking team and help shape the future of employee benefits sales. Apply now and grow with us!

In every industry there is a company that thinks, and does things, differently. In employee group benefits, GroupHEALTH Benefits Solutions™ is that company.
GroupHEALTH is transforming the way Canadians experience benefits by developing and delivering the most affordable, configurable, and usable benefit solutions to businesses across Canada. Leaders in employee benefits plans and group insurance, the GroupHEALTH Family of Companies has more than 700 employees in offices in Vancouver, Surrey, Prince George, Calgary, Edmonton, Etobicoke, Woodbridge, and Barrie. With annual premiums exceeding $700 million and over $5 billion in pension assets under management, GroupHEALTH supplies market leading employee benefit services to more than 5,000 client organizations across Canada in both the public and private sectors, supporting more than 450,000 Canadians and their families.