B2B Sales Representative

GroupHEALTH Benefit Solutions; Winnipeg; On-site; CAD 75,000 - 115,000; Full time

Benefits offered by this job

Annual incentives

Qualified leads

Licensing and training support

Dynamic remote team culture

Health benefits

LLQP designation reimbursement

Job summary

GroupStrength, part of GroupHEALTH Benefit Solutions, is hiring a B2B Employee Benefits Sales Representative in Winnipeg. You will engage prospects nationwide by phone and video, driving revenue through training and a structured licensing path including LLQP.

After onboarding, you’ll advance from BDR to full B2B Sales Representative, expanding our client base with the GroupHEALTH solutions. The role offers on-site in Winnipeg with potential hybrid options after training, uncapped commissions,

Qualifications

• 1–2 years of B2B sales experience (insurance or group benefits is a plus)
• Excellent written and verbal communication skills
• Familiarity with CRM systems is an asset
• Bilingual in French is an asset

Responsibilities

• Engage with prospects nationwide via phone and video meetings to showcase GroupHEALTH employee benefits solutions
• Leverage qualified leads from the NBD team to create opportunities and close new business
• Educate prospects on business goals and guide decision-making to improve benefits plans
• Coordinate with Client Services after closing to ensure a best-in-class experience
• Collaborate with leadership to continually improve benefits offerings for clients

Skills

B2B sales

Communication

Lead generation

Cold calling

CRM familiarity

Tools

CRM systems

Job description

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.

GroupStrength is growing. As part of the GroupHEALTH Benefit Solutions family, we are expanding our teams across multiple locations to keep pace with demand. The Canadian employee benefits industry is worth more than $60 billion annually and continues to grow, and we are growing right along with it. This is an exciting time to join a company that is scaling its people, its capabilities, and its impact across the country.

This role is based in our Winnipeg office. Hybrid work options may be available for strong performers after an initial onboarding and training period

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.