Regional Sales Manager - Insurance Services Industry - (Winnipeg, Regina or Saskatoon)

InsuranceWorks.ca; Regina; Remote; CAD 70,000 - 100,000; Full time

Job summary

A leading company in the insurance services industry is seeking a Regional Sales Manager to develop and maintain key relationships across Saskatchewan and Manitoba. This remote position involves significant travel and offers a competitive base salary plus commission. Ideal candidates will have extensive experience in B2B sales and excellent communication skills, contributing to expanding market presence while delivering exceptional service to insurance partners.

Benefits

Competitive base salary plus commission structure

Excellent growth opportunities

Qualifications

• 5-7+ years of territory management experience.
• Proven track record in B2B sales and relationship building.
• Experience with CRM systems (HubSpot preferred).

Responsibilities

• Drive business development through marketing and sales of services to insurance adjusters.
• Build and maintain a strong network of clients.
• Organize and conduct educational presentations.

Skills

B2B sales

Relationship building

Prospecting

Closing skills

Negotiation

Communication

Education

Bachelor's degree in marketing or business administration

Tools

CRM systems

Job description

Regional Sales Manager - Insurance Services Industry - Winnipeg, Regina or Saskatoon

Location : Remote with travel requirements

Compensation : Competitive base salary plus commission structure

Role Overview : This field-based position offers the opportunity to work remotely while developing and maintaining key relationships within the insurance industry across Saskatchewan and Manitoba. The successful candidate will play a crucial role in expanding our client's market presence and delivering exceptional service to insurance partners.

Key Responsibilities :

• Drive business development through marketing and sales of services to insurance adjusters
• Build and maintain a strong network of clients to ensure a consistent sales pipeline
• Attend and participate in industry networking events, including golf tournaments and trade shows
• Organize and conduct educational presentations such as lunch and learns and seminars
• Coordinate with operations team on new claims and scope of work
• Develop relationships with local accommodation vendors
• Maintain detailed activity reports and territory analyses
• Contribute to service improvements based on market feedback
• Assist in resolution of customer concerns
• Maintain accurate CRM records
• Travel requirement : approximately 50%

Required Qualifications :

• 5-7+ years of territory management experience
• Proven track record in B2B sales and relationship building
• Bachelor's degree in marketing or business administration (asset)
• Experience with CRM systems (HubSpot experience preferred)
• Demonstrated ability to meet sales targets
• Strong prospecting and closing skills

Core Competencies :

• Exceptional emotional intelligence and self-awareness
• Strong leadership and coaching abilities
• Cultural sensitivity and customer service orientation
• Advanced negotiation and presentation skills
• Excellent communication abilities (verbal, written, and listening)
• Strong organizational and time management skills
• Problem-solving and decision-making capabilities
• Ability to deliver results under pressure
• Adaptable and solution-oriented approach

The ideal candidate will be outgoing, entrepreneurial, and comfortable with frequent client entertainment activities. Insurance industry experience is beneficial but not required.

Working Arrangement : This is a home-based position with regular travel throughout Manitoba and Saskatchewan.

Qualified candidates are invited to submit their resume in confidence. Our client offers a competitive compensation package and excellent growth opportunities within a rapidly expanding organization.

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