Join Our Life & Living Benefits Team!

we are hiring

Job Position: Life & Living Benefits Associate

Job Category: Financial Services

Are you ready to kickstart an exciting career in sales? We’ve got the perfect opportunity for you! We’re looking for a vibrant and motivated individual to join us as a Life & Benefits Associate.

Discover how you can make a difference in the lives of individuals, families and communities in Saskatchewan. With Harvard Western Insurance, you’ll receive training and support to help build your knowledge and get your career on the right path. We offer competitive compensation and ongoing recognition for your achievements.

Position Overview:

  • This is an entry-level sales position where your primary focus will be generating leads and setting up meetings for our dynamic sales team.
  • While support duties are part of the role, the core emphasis is on driving sales and honing your skills towards an advisor position in the future.
  • Whether you have prior sales experience or a strong desire to dive into the world of sales, we encourage you to apply and be part of our thriving team.


tablet on yellow background with photos of the HWI executive team(full yellow)

What You Can Look Forward To:

  • Be a member of our inclusive culture alongside an extraordinarily talented community of people from various backgrounds.
  • Peer-to-peer networking, educational and training opportunities.
  • An innovative salary structure that can provide you with an ongoing lucrative bonus’.
  • Access to our pension plan with Canada Life.
  • Group Benefits insurance plan to include health and dental benefits.
  • A flex-time work environment to accommodate personal needs and encourage lifelong learning through education and training opportunities.
  • Access to Inkblot program to provide support for your wellness and mental health needs.
  • The Hill Companies Wellness Program promotes the health and well-being of employees by offering a participation reimbursement for fitness activities.

Key Responsibilities Include:

  • Employ proactive outreach and networking to expand the pool of prospective clients.
  • Take charge of scheduling and organizing meetings for the sales team with potential clients.
  • Provide essential support to the sales team in their efforts to secure new clients and maintain existing relationships.
  • Offer assistance and support to the advisor team in various operational and administrative tasks.
  • Maintain accurate and updated records of leads, meetings, and other pertinent sales-related information.
  • Engage in ongoing learning and skill development to enhance sales and support capabilities.


  • Clear and effective verbal and written communication abilities to engage with potential clients and collaborate with team members.
  • A customer-centric mindset with a focus on understanding and addressing the needs of clients to build lasting relationships.
  • Ability to work collaboratively within a team, supporting colleagues and contributing to a positive and productive work environment.
  • Strong organizational and time management abilities to handle multiple tasks and prioritize activities effectively.
  • Flexibility and adaptability to thrive in a dynamic and fast-paced work environment, adjusting to evolving priorities and challenges.
  • Basic proficiency in using digital tools, including email and other sales-related software.
  • A high school diploma or equivalent is typically required for entry-level sales positions. Additional relevant certifications or coursework may be beneficial.

About Our Company:

Harvard Western and its predecessor firms have been privileged to provide insurance for this community for over 100 years. Harvard Western is one of Saskatchewan’s largest insurance brokers and is proud of its commitment to the community of Regina and the surrounding area.

Join our growing team to help with our vision of spreading insurance literacy and financial security to Saskatchewan residents through utilizing insurance and innovative solutions.

Apply now and become a part of our amazing team!

Apply Now 

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