Client Retention Rep

GroupStrength Benefits Direct; Winnipeg; On-site; CAD 45,000 - 50,000; Full time

Benefits offered by this job

Annual and quarterly incentives

Training and development support

On-site team culture

Health and wellness benefits

Job summary

GroupStrength Benefits Direct is seeking a Client Retention Representative to engage with existing GroupHEALTH clients, gather feedback, and address concerns in collaboration with the Client Experience and Client Service teams. The role focuses on strengthening relationships and ensuring client satisfaction in a dynamic on-site Winnipeg environment.

The successful candidate will have 3–5 years in sales or retention, a business degree, strong communication and problem-solving skills, and

Qualifications

• Bachelor's Degree or College Diploma in business (asset)
• 3–5 years in sales or customer retention
• Group benefits experience is an asset
• Strong problem-solving abilities and customer service focus
• Highly organized with attention to detail and ability to manage multiple priorities

Responsibilities

• Reach out to existing clients to collect feedback through Client Experience surveys.
• Diffuse escalated situations and support clients with the Client Experience and Client Service teams.
• Collaborate with customer service and analytical teams to enhance client experience.
• Maintain and update client interactions in the CRM system.
• Manage a caseload with regular follow-ups and complete a minimum of 15 surveys per week.
• Request reference letters from clients with exceptional experiences.

Skills

Communication

Problem-solving

Customer service

Organizational skills

MS Office

Teamwork

Education

Bachelor's or Diploma in business

Tools

MS Office

Job description

Job Category: Sales & Business Development

Requisition Number: CLIEN004824

• Posted : August 31, 2026
• Full-Time
• On-site

Locations

Showing 1 location

Winnipeg, MB R3A0A3, CAN

Description

ABOUT US

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 Client Retention Representative, you will be the voice that keeps our client relationships strong. You'll connect with existing GroupHEALTH clients to understand how they're feeling about their experience, surfacing concerns early and working alongside our Client Experience and Client Service teams to resolve them. Your ability to listen, problem-solve, and build trust will play a direct role in keeping clients engaged and confident in their choice to partner with GroupHEALTH.

WHAT TO EXPECT

Your onboarding journey at GroupStrength is designed to set you up for success:

• Your first 30 days will focus on completing our Client Experience Training Course, beginning conversations with clients, and learning the fundamentals of our retention process.
• Over the next 60 days, you'll build proficiency in the client survey process and begin reviewing flagged or unhappy clients directly with your Client Experience Lead.
• By 90 days, you'll be confidently managing your own survey caseload, reporting on progress, and contributing ideas for process improvements.

YOUR IMPACT

• Contact existing clients to complete Client Experience surveys, gathering honest feedback on their experience with GroupHEALTH.
• Diffuse escalated situations and provide support to clients in partnership with the Client Experience and Client Service teams.
• Work closely with our customer service and analytical teams to deliver the best possible client experience.
• Track all client interactions and data in our CRM system (easy to use and mobile friendly).
• Manage your caseload effectively, ensuring regular, consistent follow-up.
• Complete a minimum of 15 client experience surveys per week.
• Request reference letters from clients who've had exceptional experiences with GroupHEALTH.
• Support other departments and internal team members as needed, including customer service and underwriting.
• Maintain strong knowledge of the Canadian employee benefits industry and GroupHEALTH's value-added offerings.
• Participate in regular retention meetings and ongoing retention training.
• Stay aware of the competitive landscape and use that knowledge to support client appeasement and retention strategies.

THIS IS YOU

• A driven, empathetic communicator who genuinely cares about client outcomes.
• Bachelor's Degree or College Diploma (business major an asset but not required).
• 3-5 years of experience in a sales or customer retention role.
• Group benefits insurance experience is an asset.
• Strong problem-solving skills with the ability to quickly identify the root cause of client issues.
• Exceptional customer service skills with the ability to empathize with clients.
• Highly organized with the ability to manage multiple priorities and maintain strong attention to detail.
• Intermediate to advanced knowledge of MS Office (Word, Excel, PowerPoint, Outlook).
• Comfortable following established processes while bringing forward ideas for improvement.
• Thrives in a performance-based, team-oriented environment.

YOUR COMPENSATION

At the time of this posting, the estimated annual base salary for this position is $45,000–$50,000. Individual compensation within this range will depend on factors such as job-related skills, relevant experience, and education/training. This reflects the base salary only and does not include our comprehensive total rewards package.

WHAT YOU'LL GET

In addition to a competitive base salary and benefits, you'll enjoy:

• Annual and Quarterly Performance Incentives
• Ongoing Training and Development Support
• A Dynamic On-site Team Culture

We also offer comprehensive health and wellness benefits, including employee wellness activities.

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.