Regional Manager, Individual - Life (External Wholesaler)

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Date: Oct 21, 2026

Location: North York - Toronto, ON (Hybr, CA

Company: Wawanesa Insurance

Job ID: 10443 


Employment Type: Existing Role 

 

Work Environment: We offer a hybrid work environment that offers flexibility to our employees in balancing in-office (2 days per week OR 15 hours per week in a Wawanesa office) and remote work. You may work from any of the following locations: Toronto (North York), ON.

 

Working Business Language: English 
 

Salary: At Wawanesa, salary is only one component of a holistic, comprehensive and competitive offering that we provide to our employees. In addition to salary, full-time and part-time permanent employees are eligible for an annual bonus plan, leave of absence top-up programs and provided with generous vacation time, personal days, premium free benefits and pension plan. 
 

The salary offered for this role is determined with consideration to various factors, including but not limited to: your work location, local labour market conditions, external market salary data, internal pay equity and the knowledge, skills, experience and anticipated proficiency in the role. The salary offered is estimated to be within the following range: $85,000 - $100,000 (base pay range plus variable monthly commission based on sales. Approximate total yearly income during the first year is $150-160k+) Candidates with salary expectations outside of the range are still encouraged to apply. 

 

About The Wawanesa Mutual Insurance Company
Founded in 1896, The Wawanesa Mutual Insurance Company is one of Canada’s largest mutual insurers, fully owned by its more than 1.8 million members. Headquartered in Winnipeg, Wawanesa is the parent company of WSI™, a specialty insurer delivering tailored solutions built around unique needs; Wawanesa Life, a provider of life insurance products; and Western Financial Group, a leading national distributor of personal and commercial insurance.

Wawanesa is committed to helping communities thrive in a changing world. The company invests more than $4 million annually in charitable initiatives, including $2.5 million each year to support people and communities on the front lines of climate change. Learn more at wawanesa.com.

 

We are currently seeking dedicated, driven, and enthusiastic individuals who thrive in a dynamic environment, embrace change, and are eager to gain diverse experience while advancing their careers as part of a growing team.

 

Job Overview

The Regional Manager is responsible for planning and executing the Annual Business Plan to achieve sales targets within the Ontario territory (Eastern GTA - Toronto, Scarborough, Pickering, Woodbridge Markham, Oshawa etc) . This role involves building and maintaining a strong broker network and promoting Wawanesa Life as a leading insurance provider.

 

Job Responsibilities

  • Appointing, training, and developing broker relationships.
  • Strong team player with the ability to collaborate effectively with Head Office personnel.
  • Excellent communication skills, including verbal, written, and listening.
  • Effective decision-making and problem-solving abilities.
  • Commitment to personal development and staying current with industry changes.
  • In-depth knowledge of Wawanesa Life products, underwriting, and administration practices.
  • Strong business acumen and negotiation skills.
  • Proficiency in using Microsoft Office (Word, Excel, PowerPoint, PowerBI).
  • Experience with CRMs including Salesforce considered an asset.

Sales Development (90%):

  • Develop and implement the Annual Business Plan with a strong focus on achieving sales targets.
  • Manage the territory in alignment with the Business Plan and company objectives.
  • Build new broker relationships, ensuring they meet company standards.
  • Provide quarterly feedback on year-to-date sales activities and results.
  • Manage activities within the allocated expense budget.

Other Responsibilities (10%):

  • Act as a liaison between Head Office, brokers, and clients to resolve issues and enhance service levels.
  • Promote sales and marketing tools.
  • Monitor competitive marketplace changes and consumer/marketing trends.
  • Collaborate with the Head Office team to develop new product opportunities based on market trends and broker feedback.

Qualifications

  • Ability to be licensed within 90 days or currently licensed to transact life insurance sales in Ontario.
  • 5+ years of proven sales experience, with a focus on initiating contact, presenting, and closing deals.
  • Preference will be given to those candidates with a university degree and/or industry designations such as CLU, CFP or CHS.
  • Ability to work independently and under minimal supervision.
  • A valid driver’s license.
  • Travel within the region as outlined in the Business Plan, including overnight travel when necessary.
  • Travel to Head Office as required. 

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Diversity Equity, Inclusion & Belonging

At Wawanesa, we are committed to Diversity, Equity, Inclusion and Belonging (DEIB) and believe that our strength lies in the diversity of our people – this is supported by having a representative workforce.

We welcome applications from all qualified candidates, including racialized persons, women, Indigenous Peoples, persons with disabilities, members of the 2SLGBTQIA+ community, gender-diverse and neurodiverse individuals, and anyone who can contribute to the further diversification of thought and ideas. 
 

We aim to ensure our recruitment process is accessible to all candidates. If you require accommodations during any stage of the recruitment process, please reach out in confidence to jobs@wawanesa.com.
 

All Wawanesa job applicants are subject to Wawanesa's Privacy Policy.

Please note that the recruitment process for this position may involve the use of AI tools to screen, assess, or select applicants. All final decisions are taken or reviewed by human recruiters and human hiring leaders in compliance with all applicable legislation.