Senior Executive Assistant

Wawanesa Insurance•Winnipeg, MB

9d•CA$65,000 - CA$75,000•Hybrid

About The Position

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.

Requirements

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.

Nice To Haves

Familiarity with the Property & Casualty insurance industry would be considered an asset.

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.