Executive Assistant

Gore Mutual has a long-standing tradition of supporting Canadian communities. As Canada's first property and casualty insurer, we've been proudly built by and for Canadians for over 185 years. 
Insurance that does good
 isn't just what we do—it's why we exist. Now, we're building on that legacy. Fueled by investments in talent and technology, our bold strategy to transform is nearly complete. Our path forward sharpens our focus on business performance and our ambition to transform our company—and our industry—for the better. With our intent to merge with Beneva in 2026, we'll unite two well-established, financially strong, and trusted brands to become the strongest mutual insurer in Canada—giving Canadians purpose-driven insurance options for generations to come. When you join Gore Mutual, you'll be empowered to
Lead the way, make a difference
, and grow your career. We believe true leadership happens at every level and are committed to building an inclusive, diverse, and collaborative workplace—a place where people are empowered to lead, share ideas, and make meaningful contributions. Here, your ideas matter, your voice is heard, and your work will drive real impact. If this sounds like a place where you want to be, come join us.

The Executive Assistant provides daily efficient, professional, and confidential support to the assigned C-Suite(s) members and, in some cases, their functionally aligned VP. The Executive Assistant will drive functional synergies by providing additional administrative support to functionally aligned Executives.

What will you be doing in this role?

Accountability # 1: Calendar & Inbox Management

• Calendar, Inbox Ownership and Management to assigned C-Suites
• Calendar Ownership and Management of functionally aligned VP's.
• Ensure all necessary information and documentation are included that are required for all meetings.
• Ensure days, weeks, and months are streamlined, efficient and manageable.
• Responsible for preparing agendas, setting up meetings with external and internal parties.
• Support and assist functionally aligned VPs with calendar management to clear up any conflicts and assist with booking meetings.

Accountability # 2:  Meeting Coordination

• Manage all details for on/off-site meetings including registration, travel, transfers, accommodation, communication, meals, equipment and meeting materials.

Accountability # 3:  In-Person Meeting and Event Presence

• Attend any in-Person Meeting or event held at both Cambridge or Toronto Office locations when presence and support is requested.
• Presence required from the start to the end of meeting or event, unless otherwise communicated.

Accountability # 4:  Financial Management Support

• Expense report tracking, submission, and approvals on behalf of C-Suites and VPs
• Responsible for Admin budgeting, tracking and approvals.

Accountability # 5:  Communication

• Support with general function communication when necessary.

What will you need to succeed in this role?

• Community college degree in Administrative or Business Management, Communication, Project Management required or Undergraduate degree in the same field in Administrative or Business Management preferred.
• 5+ years of experience required as Executive Assistant to C-Suite
• 5+ years of experience working with Microsoft Office 365
• 5+ years of Administration experience
• 3+ years of Expense Tracking/Submission experience
• Extensive experience with calendar and inbox management for C-Suite Executives
• Proven organizational  and strong prioritization skills.
• Ability to work under pressure and within deadlines.
• Strong multitasking skills
• High degree of confidentiality and ability to work with sensitive and confidential matters.
• Strong attention to detail and proof-reading
• Strong verbal and written communication skills
• Financial acumen regarding budget process and planning
• High level of diplomacy, discretion, and facilitation skills
• Experience collaborating with shareholders, Board of Directors, Executive Management, and regulators.
• Able to set own expectations and delivers above and beyond.

Accessibility for applicants

Gore Mutual Insurance Company is committed to providing accommodations for people with disabilities during all phases of the recruiting process, including the application process.

If you require accommodation because of a disability, we will work with you to meet your needs. Contact us and a human resources representative will consult with you to determine an appropriate accommodation.

Should you request an accommodation during the interview process, please notify your Talent Acquisition Consultant.