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GroupHEALTH Benefit Solutions

B2B Sales Representative (Onsite - Winnipeg)

Winnipeg, MB, R3A 0A3, Canada

Full-time

Apply on recruiting.ultipro.ca About employer

Applications open in a new tab.

Job details

Job type: Full-time
Experience: 1-2 years of B2B sales experience (experience in insurance or group benefits is a plus).
Posting language: English
Posted: Nov 12, 2026

Original job description

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 first two weeks will be focused on studying for your LLQP (Life License Qualification Program) to ensure you’re fully licensed and ready to excel in the role.
After obtaining your LLQP license, you’ll embark on our comprehensive training program, beginning as a Business Development Representative (BDR). In this role, you’ll learn about our company, our target market, and - most importantly - our industry-leading products.
As you progress through the training program and hit key milestones, you’ll graduate to the role of B2B Sales Representative, where you’ll apply your newfound knowledge and skills to make a significant impact.

YOUR IMPACT

You'll communicate with Canadian business leaders about their current employee benefits plans and demonstrate how GroupHEALTH can provide superior solutions.
Leverage qualified leads from our New Business Development (NBD) team to create opportunities and consistently close new business at or above quota.
Educate and guide prospects through the decision-making process, assessing and understanding their business goals.
Collaborate with business leaders to evaluate and improve their benefits plans using your expertise and GroupHEALTH tools. You’ll create customized solutions that outperform their existing plans - no apples-to-apples comparisons here, only superior results.
Once your prospect agrees to move forward with GroupHEALTH, you'll hand them over to our dedicated Client Services team, ensuring they receive a best-in-class experience.
Our top Sales Advisors continuously hone their skills through prospecting. During your training, you'll gain hands-on experience working with our BDR team to further develop your sales capabilities.

THIS IS YOU

A driven self-starter with a strong desire to succeed.
1-2 years of B2B sales experience (experience in insurance or group benefits is a plus).
Exceptional communication skills, both written and verbal.
Quick thinker with a knack for technology.
Experience in cold calling and lead generation.
Familiarity with CRM systems is an asset.
Bilingual in both spoken and written French is an asset.

YOUR COMPENSATION

On-target earnings Year 1: $75,000+
On-target earnings Year 2: $90,000+
On-target earnings Year 3 onward: $115,000+

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:

Annual and Quarterly Sales Incentives
Qualified Leads
Licensing and Training Support
A Dynamic Remote Team Culture

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!

Apply on recruiting.ultipro.ca About employer

More about this job

Responsibilities

You will engage with prospects nationwide to showcase employee benefits solutions and guide them through the decision-making process. Additionally, you will collaborate with business leaders to evaluate and improve their existing benefits plans using company tools.

Requirements

Candidates should have 1-2 years of B2B sales experience and strong communication skills. Familiarity with CRM systems and cold calling is considered an asset for this role.

Skills

B2B sales
Cold calling
Lead generation
Communication skills
CRM systems
Insurance
Group benefits
Negotiation
Prospecting
Business development

Benefits

Health insurance
Wellness benefits
Licensing support
Training support
Sales incentives
Commission

Visa sponsorship

Not detected in the job text

Keywords

B2B Sales
Group Benefits
Insurance
LLQP
Business Development
Cold Calling
Lead Generation
CRM
Sales Quota
Client Services
Prospecting
Employee Benefits
Sales Advisor
Business Development Representative
Commission

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