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. Contribute to the execution of the national business development strategy by translating strategic priorities into regional market actions.

Build, lead, and coach the ontario group benefits sales team as the regional business evolves. Provide senior-level support and guidance on complex or sensitive cases to help sales managers protect client relationships and advance business objectives. Actively contribute market intelligence and field insights to support product development, process optimization, and the organization’s competitive positioning.

Develop, expand, and manage distribution channels in alignment with the organization’s selected go-to-market and growth strategies. Work 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. Participate in setting annual and long-term objectives that drive profitable growth, strengthen market penetration, and maximize business opportunities.

Identify, qualify, and develop new business opportunities with a explicit focus on sustainable revenue generation and long-term strategic fit. Monitor market trends, competitor activity, broker needs, and emerging opportunities to inform regional priorities and strategic decision-making.



Establish, track, and analyze performance indicators to ensure achievement of sales, growth, and market development targets.

Represent the organization at industry conferences, broker events, and market forums, while building a strong and influential network of contacts within the group benefits sector. Support product marketing strategies by providing regional insight, partner feedback, and recommendations that strengthen the company’s market relevance and sales effectiveness. 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. 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. High standards of quality, professionalism, ethics, and customer service.

📌 Territory Sales Manager, Grocery (Winnipeg)
🏢 Humania Assurance
📍 Winnipeg