EXECUTIVE ADMINISTRATIVE ASSISTANT, EVP - PAYER SOLUTIONS

Green Shield Canada • Toronto, ON

3d • CA$51,383 - CA$79,261

About The Position

This role is for an Executive Assistant who is genuinely excited about 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.

Requirements

• 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.
• 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.

Nice To Haves

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

Responsibilities

• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: Associate degree