Regional Sales Director in Winnipeg

Regional Sales Director in Winnipeg

Winnipeg Full-Time 121500 - 148500 $ / year (est.) Hybrid
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At a Glance

  • Tasks: Lead a dynamic sales team and drive growth in the Group Benefits sector across Ontario.
  • Company: Join a leading insurance company focused on innovation and strategic partnerships.
  • Benefits: Competitive salary, professional development, and opportunities for career advancement.
  • Other info: Work in a fast-paced environment with a focus on collaboration and results.
  • Why this job: Make a real impact by shaping the future of group benefits in a growing market.
  • Qualifications: 6-9 years in insurance sales with leadership experience; strong communication skills required.

The predicted salary is between 121500 - 148500 $ per year.

Join us as Regional Sales Director and lead the growth of our Group Benefits business across Ontario while supporting expansion in Western Canada. You will build strategic partnerships, lead a high-performing sales team, and drive revenue growth and market development in key regions.

Establish, cultivate, and sustain relationships with brokers, third-party administrators (TPA), third-party payers (TPP), and other key distribution partners. Contribute to the execution of the national business development strategy by translating strategic priorities into regional market actions.

Your core responsibilities include:

  • Developing, expanding, and managing distribution channels in alignment with the organization’s selected go-to-market and growth strategies.
  • Working closely with the sales team to design and implement effective sales tools, value propositions, and market-facing resources for both internal teams and external partners.
  • Participating in setting annual and long-term objectives that drive profitable growth, strengthen market penetration, and maximize business opportunities.
  • Identifying, qualifying, and developing new business opportunities with a clear focus on sustainable revenue generation and long-term strategic fit.
  • Monitoring market trends, competitor activity, broker needs, and emerging opportunities to inform regional priorities and strategic decision-making.
  • Establishing, tracking, and analyzing performance indicators to ensure achievement of sales, growth, and market development targets.
  • Representing the organization at industry conferences, broker events, and market forums, while building a strong and influential network of contacts within the group benefits sector.
  • Supporting product marketing strategies by providing regional insight, partner feedback, and recommendations that strengthen the company’s market relevance and sales effectiveness.

Desired Profile:

  • Bachelor’s degree in a related field, or an equivalent combination of education and relevant professional experience.
  • Minimum of 6 to 9 years of experience in insurance sales, including at least 3 years in a sales leadership or team management role.
  • Strong knowledge of the insurance and group benefits industry, including distribution models, broker networks, and market dynamics.
  • Established relationships with managing general agencies (MGAs), brokers, advisors, and other relevant market partners.
  • Excellent written and verbal communication skills in English.
  • Entrepreneurial mindset, with the ability to identify opportunities, open new markets, and build momentum in a developing territory.
  • Strategic, client-focused approach with strong business acumen and a sound understanding of partner and advisor needs.
  • Ability to adapt quickly, navigate ambiguity, and remain effective under pressure in a competitive sales environment.
  • Strong coaching and people leadership skills, with the ability to build engagement, accountability, and performance within a sales team.
  • Excellent interpersonal skills, executive presence, and ability to represent the organization with credibility and professionalism.
  • Strong analytical, negotiation, and problem-solving skills.
  • High standards of quality, professionalism, ethics, and customer service.
  • Autonomous, proactive, and results-oriented leadership style.
  • Ability to influence and collaborate effectively with multiple internal and external stakeholders.
  • Solution-driven approach with a strong focus on execution, follow-through, and measurable outcomes.

Are you interested in this position? Note that our offices are located in Saint-Hyacinthe.

Regional Sales Director in Winnipeg employer: Humania Assurance Inc.

At Humania, we pride ourselves on being an exceptional employer that fosters a collaborative and innovative work culture. As a Regional Director in Group Benefits Sales & Growth, you will have access to comprehensive benefits, professional development opportunities, and the chance to make a significant impact in the Ontario market and beyond. Our commitment to employee growth and a supportive environment makes Humania a rewarding place to advance your career while contributing to meaningful change in the industry.

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Contact Details:

Humania Assurance Inc. Recruitment Team

We think you need these skills to ace Regional Sales Director in Winnipeg

Sales Leadership
Strategic Partnerships
Revenue Growth
Market Development
Relationship Management
Business Development Strategy
Team Coaching