Job ID: 10149

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: Winnipeg, MB.

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: $65,000 - $75,000. 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, 100% owned by its members, with more than $4.1 billion in annual revenue and $12.5 billion in assets. Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of personal and business insurance. In March of 2026, Wawanesa entered into an agreement to acquire Everest Insurance Company of Canada to strengthen its commercial insurance capabilities and advance its long-term growth strategy.

Wawanesa proudly serves more than 1.8 million members and we are home to more than 3,000 employees across Canada. The company actively gives back to organizations that strengthen communities, donating more than $4 million annually to charitable organizations, including more than $2 million each year in support of people on the front lines of climate change. Learn more at wawanesa.com.

We are currently looking for dedicated, driven, and enthusiastic individuals who thrive in an environment that welcomes change and are looking for an opportunity for diverse experience and advancement on a growing team.

Job Overview

The Senior Executive Assistant serves as a trusted partner to the Chief Risk Officer, delivering high-level administrative support while demonstrating sound judgment, maintaining confidentiality, and upholding a professional and polished representation of the organization.

The deadline to apply for this role is: Wednesday, July 8, 2026.

Job Responsibilities

Manage a complex executive calendar, prioritizing meetings, resolving conflicts, and ensuring deadlines are met. Prepare and compile executive and Board-level materials, including reports, presentations, and research. Coordinate meetings end-to-end, including agendas, materials, logistics, minutes, and follow-up on action items. Manage and prioritize incoming correspondence, including email, exercising sound judgment and responding on behalf of the SVP as appropriate. Interact professionally with senior internal leaders and external stakeholders, including Board members. Maintain organized and confidential filing systems (electronic and paper-based). Provide coordination and direction to senior leaders and stakeholders to ensure timely delivery of materials and reports. Exercise proxy authority for approvals and administrative processes (e.g., expenses, transactions). Coordinate travel, departmental meetings, and team events, ensuring alignment with policies and procedures. Conduct research and prepare reports to support executive decision-making and strategic initiatives. Collaborate with peers, business partners, and Senior EA team to support initiatives and continuously improve service delivery. Streamline and document processes to enhance efficiency. Provide backup support to other Senior Executive Assistants and support additional projects as required.

Qualifications

Minimum 5 years’ experience in a senior executive support role. Related post-secondary education strongly preferred. Strong general computer skills with basic IT trouble shooting abilities. Strong MS office skills; inclusive of Word, Excel and PowerPoint. Ability to maintain a high level of discretion when handling confidential information. Strong verbal and written communication skills with a demonstrated ability to interact with all levels of internal and external customers. Strong organizational skills with an ability to prioritize tasks and manage time effectively. Ability to manage multiple projects, tasks and assignments at once, reprioritizing where necessary. Ability to address details and examine work carefully for accuracy and completion. Familiarity with the Property & Casualty insurance industry would be considered an asset.

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.