WHO WE ARE

When it comes to health, we’re always looking for ways to push for better. It’s why we were founded in the first place. In 1957, our founder, pharmacist William Wilkinson, witnessed a mother sacrifice her health by forgoing her own medicine to pay for her sick daughter’s prescription. He knew there had to be a better way. So, he introduced North America’s first prepaid drug plan, and GreenShield was born as a non-profit with a mission to support better health for all Canadians.

We aren’t just a health and benefits company. We’re the only non-profit social enterprise that brings worlds of coverage and care together, all in one place.

We’re noble challengers, purposefully building a better way and we need the best people to help us create a more holistic approach that takes care of the mind and body.

Our mission is to create better health for all Canadians, and we know that starts with our employees.

THE ROLE IN A NUTSHELL

Base Salary: CAD $51,383.00 - 79,261.00

We’re looking for someone who is genuinely excited about being an Executive Assistant and takes pride in the craft of enabling a senior leader to be at their best. Reporting to the Executive Vice President, Head of Payer Solutions, this person will serve as a trusted partner who enables the EVP to lead with focus, pace and discipline. The successful candidate will thrive in a fast-moving, complex environment where professionalism, sound judgment, confidentiality and flexibility are essential.

This is an opportunity to support a significant enterprise mandate as GreenShield advances its 2030 strategy, deepens its integrated Payer-Provider model and brings coverage and care together as One GreenShield. As Payer evolves to bring together Insurance, Claims Adjudication, Benefits Administration and third-party administration, the Executive Assistant will help the EVP translate strategy into a clear operating rhythm across Payer, Provider, Client Segments and enterprise functions. The role will manage priorities, information flow, stakeholder interactions and executive cadence, ensuring decisions are well prepared, commitments remain visible and disciplined follow-through is sustained.

Key Responsibilities

Executive Operations & Strategic Support:

- Act as an extension of the EVP, helping translate strategic priorities into a disciplined operating rhythm across Payer. 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 and the integrated Payer–Provider model by tracking priorities, dependencies, decision points and enterprise commitments.
- Support cross-functional work across Payer, Provider, Client Segments and enabling functions, surfacing trade-offs, escalation needs and gaps in follow-through.
- Attend selected meetings, capture decisions and actions, and maintain clear ownership through to completion.

Relationship Management &

• Enterprise Connectivity:

- Build trusted working relationships with Executive Assistants, Payer leaders, Provider and Client Segment partners, and key enterprise stakeholders.
- Represent the EVP professionally 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 the EVP’s complex calendar across the Payer leadership team, Executive Committee and key enterprise and external partners.




- Protect time for the highest-value strategic, operational and relationship priorities while preserving flexibility for emerging needs.
- Build in preparation, travel and follow-up time so the EVP is ready for decisions, presentations and stakeholder meetings.
- Maintain forward visibility of commitments, deadlines and decision points, resolving conflicts before they become barriers.

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 Payer 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.

WHO WE'RE LOOKING FOR

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

- Post-secondary education or an equivalent combination of education and progressively senior administrative experience.
- Significant experience supporting a C-suite executive or comparably senior leader in a complex organization.
- Excellent interpersonal and communication skills, both verbal and written.
- Demonstrated ability to work flexibly, manage changing deadlines and respond calmly to urgent priorities.
- 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.
- Strong written and verbal communication skills, including the ability to prepare polished executive materials.
- Experience in financial services, insurance, perks administration or another regulated environment is an asset; bilingualism in English and French is also an asset.

THE CULTURE We believe a career should be meaningful. Not just a means to earn a living. Our culture is one where everyone's voice is heard and valued. Because that’s what it takes to create better health for all. We dare to challenge the status quo. And we’re driven by people who have challenged theirs. We believe that your workplace should empower you to be the best version of yourself. That’s why we provide a place where you can be inspired, challenged, and rewarded.

Where your growth means our growth.

Where your voice is heard and valued.

Where your work has purpose. And purpose matters.

We believe our people are critical to our overall success. Inclusivity makes us a stronger, smarter and more informed organization. Being intentionally inclusive of diverse backgrounds, perspectives and experiences will enhance our company culture to positively impact how we support our communities. A career at GreenShield isn’t just about personal achievements, it's about making a difference together.

Here’s to Better Health for All!

A FEW MORE DETAILS

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.

GS supports diversity, equity and inclusion in our teams and communities, and we value the unique contributions made by all. Even if your experience doesn’t align perfectly to every requirement, we invite you to apply. We encourage applications from all candidates and will accommodate needs under human rights legislation throughout all stages of the recruitment and selection process.

Please let us know of any accommodation through [email protected]. Information received relating to accommodation will be addressed confidentially.

Providing this information gives GS consent to use your personal information to assess your suitability for specific positions, future opportunities or for your personnel file. Your résumé will be held in strict confidence and will be viewed only by the Organization. Information may be stored outside of Canada and could be used for aggregate statistical purposes (which uses no personal identification).

AI Usage - GreenShield leverages AI to help produce Job Descriptions, and ideate on interview questions. We also leverage AI for interview transcription support.

📌 EXECUTIVE ADMINISTRATIVE ASSISTANT, EVP - PAYER SOLUTIONS (Toronto)
🏢 Green Shield Canada
📍 Toronto