Insurance Executive Assistant Jobs in Toronto, ON

Logic Executive Search & Workplace Solutions is proud to partner with GreenShield in the recruitment of an Executive Assistant based out of Windsor or Toronto, Ontario.

GreenShield is a purpose-driven organization on a mission to redefine healthcare in Canada. As the country's first integrated payer-provider, GreenShield brings together insurance, benefits administration, pharmacy, mental health, and healthcare services to create a more connected and accessible healthcare experience. Guided by its commitment to "Better Health for All," GreenShield combines innovation, compassion, and social impact to improve the well-being of individuals, families, and communities across Canada.

Job Purpose:

We’re looking for someone who is excited about continuing their career as an experienced Executive Assistant and takes pride in the craft of enabling a senior leader to be at their best to achieve priorities and goals. Reporting directly to the Executive Vice President, Head of People and Culture, the Executive Assistant will serve as a trusted partner who enables the EVP to lead with focus, pace, and discipline. This requires the ability to thrive in a fast-moving, complex environment where you will need to anticipate needs, exercise sound judgment and decision-making, confidentiality, navigate competing priorities, and represent the EVP with professionalism and credibility both internally and externally.

Position Availability:

· This posting is for a vacancy within the organization

What’s In It For You?

· Base Salary Range: $85,000 - $95,000

· Hybrid Work Environment

· Comprehensive Benefits That Start on Day 1

· Direct Contribution Pension Plan Available

· The Opportunity to Work for Canada’s Largest Non-Profit Health and Benefits Company

Key Responsibilities:

Executive Operations & Strategic Support:

· Serving as a trusted advisor and strategic partner to the EVP, help translate strategic priorities into disciplined action plans.

· Coordinate Executive Committee, CEO and Board-related inputs, reports and presentations from initial request through final submission.

· Connect the EVP’s agenda to GreenShield’s 2030 strategy by tracking priorities, dependencies, decision points and commitments.

· Attend selected meetings, capture decisions and actions, and maintain clear ownership through to completion.

· Develop a deep understanding of the EVP’s working style, priorities, preferences, and decision-making approach.

Relationship Management:

· Represent the EVP professionally, build relationships, and create a responsive, well-coordinated experience for internal and external stakeholders.

· Maintain awareness of stakeholder expectations and organizational dynamics, helping the EVP engage the right people at the right time.

Calendar Management & Prioritization:

· Own and optimize the EVP’s highly complex and dynamic executive calendar.

· Protect time for the highest-value strategic, operational and relationship priorities while preserving flexibility for emerging needs.

· Balancing competing priorities while ensuring appropriate preparation time, travel time, focus time, and stakeholder engagement so the EVP is ready for decisions.

· Maintain forward visibility of commitments, deadlines and decision points, resolving conflicts before they become barriers.

· Continuously evaluating and re-prioritizing commitments to maximize executive effectiveness.

Executive Communications & Briefing:

· Prepare and sequence the EVP’s materials for the day ahead, ensuring every meeting has the relevant context, pre-reads and decision points ready in advance.

· Draft and edit correspondence, presentations and leadership communications in the EVP’s voice.

· Synthesize complex information into clear messages, decisions, risks and next steps for executive audiences.

· Handle sensitive and time-critical communications with sound judgment, accuracy and discretion.

Leadership Forums & Decision Follow-Through:

· Coordinate leadership meetings, offsites and enterprise forums, including agendas, materials, logistics and follow-up.

· Work with leaders and partners to gather inputs, clarify decisions required and ensure materials are executive-ready.

· Maintain action and decision logs, track commitments and follow through with owners to keep priorities moving.

Inbox & Information Management:

· Actively manage and organize the EVP’s inbox, surfacing time-sensitive decisions, strategic requests and emerging issues.

· Draft or coordinate responses, maintain an effective filing system and ensure commitments are captured and followed through.

· Keep the EVP current on schedule changes, stakeholder needs and items requiring attention or escalation.

Travel, Expenses & Administrative Coordination:

· Organize domestic and occasional international travel, including itineraries, accommodations, transportation and meeting logistics.

· Anticipate schedule changes and ensure the EVP has the information and materials required while travelling.

· Manage expense reports, procurement, consultant agreements and related administrative requirements accurately and on time.

Flexibility, Anticipation & Problem-Solving:

· Operate with a high degree of independence, anticipating needs, making sound decisions and moving work forward without waiting for direction.

· Adapt to changing priorities and provide reasonable flexibility outside standard hours when urgent business needs arise.

Key Competencies:

Anticipation & Problem-Solving: Stays ahead of priorities, identifies risks early and resolves issues with sound judgment and minimal direction.

Relationship Management: Builds trust quickly and works effectively across executive, functional and external stakeholder groups.

Operational Discipline: Brings structure to complex work, maintains rigorous follow-through and keeps commitments visible.

Discretion & Confidentiality: Handles sensitive business, people and financial information with exceptional professionalism.

Business Acumen: Understands executive priorities, organizational dynamics and the importance of clear decision rights and stakeholder alignment.

Adaptability: Remains composed and effective as priorities shift, deadlines tighten, and new information emerges.

Key Selection Criteria:

· Demonstrates a genuine passion for the Executive Assistant profession and views executive support as a long-term career, taking pride in building trusted partnerships and enabling leadership success.

· Post-secondary education or an equivalent combination of education and progressively senior administrative experience.

· 7 – 10+ years of progressive executive support experience, including direct support of senior executives or C-Suite Leaders a complex organization.

· Excellent interpersonal and communication skills, both verbal and written, including preparing polished executive materials.

· Exceptional organization, prioritization and follow-through, with strong attention to detail.

· Advanced proficiency in Microsoft Outlook, PowerPoint, Excel, Word and modern collaboration and productivity tools.

· Experience in financial services, insurance, benefits administration or another regulated environment is an asset; bilingualism in English and French is also an asset.

· Proven success managing complex calendars, travel arrangements, executive communications, and high-profile stakeholder interactions.

· Exceptional organizational and project management capabilities.

· Ability to navigate rapidly changing priorities while maintaining composure and attention to detail.

· Ability to work flexible hours and work on call to meet changing priorities.

· Proficiency in English is required for this position. As part of this role, you will be required to communicate with colleagues or customers who use English as their primary language. By requiring English proficiency for this position, we aim to ensure that our employees can excel in their roles, collaborate, and communicate effectively, and contribute to the success of our organization.

Logic Executive Search and Workplace Solutions is dedicated to supporting opportunities that reflect the diversity of the communities we serve. We value diverse perspectives and experiences, and encourage individuals from all backgrounds to apply, including those who may not meet every requirement listed.

If you are interested in applying for this position, please forward a copy of your resume to angelo@logicexecutivesearch.com. We thank all those who apply for this role, however, only those selected for an interview will be contacted.

Logic Executive Search and Workplace Solutions is committed to providing accessible employment practices that follow the Accessibility for Ontarians with Disabilities Act and the Ontario Human Rights Code. Should you require accommodation during any phase of the recruitment process, please let our recruitment team know.

Our Commitment to a Human-Centered Hiring Process: We comply with Ontario employment and privacy laws while using technology responsibly, ensuring every resume is personally reviewed and all hiring decisions are guided by experienced HR professionals with a fair, transparent, and ethical approach.