Executive Assistant and Governance Lead

Circle of Care, Sinai Health • Toronto, ON

2d • Hybrid

About The Position

As an Executive Assistant & Governance Lead with Circle of Care, you will provide high-level strategic support to the Chief Executive Officer (CEO), functioning as a critical partner in navigating a complex executive ecosystem. With a high degree of professionalism and proficiency, you will manage the strategic optimization of the CEO’s complex schedule, ensuring alignment with organizational priorities. You will serve as a sophisticated liaison, managing high-stakes relationships with external partners and stakeholders with diplomacy and precision. This position is designed for a proactive problem-solver who anticipates the CEO's needs and translates vision into structured results. While you are not the architect of board strategy or meeting content, you serve as the indispensable engine of the governance cycle, ensuring the Board of Directors is seamlessly supported and all administrative requirements are met with meticulous rigor.

Requirements

• Executive partnership experience with Minimum of 7–10 years of progressive experience supporting C-Suite executives and a Board of Directors, ideally within a healthcare, non-profit, or broader public sector (BPS) environment.
• University Degree in Business Administration, Public Administration, Communications, or a related field; professional certification (e.g., CCAP, GPC.D) or Governance professional training is considered a strong asset.
• Advanced proficiency in the Microsoft 365 suite (SharePoint, Teams, OneDrive) with a proven ability to leverage Power Automate, Power BI, or AI tools to streamline executive workflows and board reporting.
• Exceptional verbal and written communication skills with a refined "executive presence" and the ability to draft high-stakes correspondence that reflects the CEO’s voice and organizational brand.
• Demonstrated ability to navigate the "executive ecosystem," using critical thinking and analytical muscle to resolve scheduling puzzles and operational bottlenecks independently.
• Ability to problem solve, prioritize, and direct workflow independently
• Strong initiative, judgment, decision-making and analytical abilities in order to manage and prioritize CEO needs
• Proven ability and effectiveness at managing high level confidential portfolios including managing highly confidential information discreetly and diplomatically
• Demonstrates autonomy and discretion to make some decisions within well-defined parameters
• Proven experience managing board cycles, including a deep understanding of bylaws, meeting protocols, and the confidentiality requirements unique to public sector organizations. Superior emotional intelligence (EQ) and discretion, with a track record of managing sensitive portfolios and external partnerships with grace, diplomacy, and absolute confidentiality.

Nice To Haves

• professional certification (e.g., CCAP, GPC.D) or Governance professional training is considered a strong asset.
• proven ability to leverage Power Automate, Power BI, or AI tools to streamline executive workflows and board reporting.
• proven experience managing board cycles, including a deep understanding of bylaws, meeting protocols, and the confidentiality requirements unique to public sector organizations.

Responsibilities

• Acts as the strategic gatekeeper and architect of the CEO’s schedule, proactively identifying priorities and resolving complex conflicts to ensure maximum executive impact and alignment with organizational goals
• Manages comprehensive end-to-end travel and engagement logistics, anticipating needs and preparing detailed itineraries that ensure seamless transitions between local and external commitments.
• Leads the operational execution of workshops and corporate events, overseeing everything from high-level agenda preparation to vendor management, while ensuring strict adherence to BPS guidelines and corporate policies.
• Drafts, synthesizes, and polishes high-stakes executive correspondence and reports, ensuring the CEO’s voice is consistently represented and that all materials are 'board-ready' and error-free.
• Oversees the flow of executive information, independently triaging communications and directing items to the appropriate leadership teams for action while tracking follow-ups to ensure closure.
• Drives the operational lifecycle of Board and Executive Committee meetings, coordinating the seamless distribution of materials, managing digital governance platforms, and ensuring the administrative framework for effective decision-making is in place.
• Acts as a liaison with counterparts within Circle of Care, and with key partners, on matters involving committees the CEO, Director(s)/VP chair or participate
• Champions the adoption and maintenance of the organization’s project management ecosystem, leveraging digital tools (such as O365 and automation) to standardize workflows and enhance executive visibility into project progress.
• Directs the creation and curation of high-impact project artifacts—including briefs, dashboards, and tracking logs—ensuring that all documentation is 'executive-ready' and provides the CEO with the critical data needed for rapid decision-making.
• Monitors project milestones and deliverables across executive portfolios, proactively flagging bottlenecks and coordinating with internal stakeholders to ensure organizational initiatives remain on track and aligned with the CEO’s vision.
• Champions a "safety-first" ecosystem as a leading advocate for a positive, blame-free culture, ensuring transparent reporting that aligns with organizational values of continuous improvement.
• Participating in maintaining a safe workplace environment by cultivating a positive safety culture and encouraging best practices to promote both staff and client safety and well-being
• Participating in all health and safety training initiatives on a regular basis
• Taking proactive action against client incidents within your scope of practice
• Protecting the wellbeing of staff by providing a safe and healthy working environment.
• Promoting a culture of safety by being responsible for encouraging blame-free reporting.
• Investigating adverse events by performing a root cause analysis and gathering all relevant information as it pertains to the event.
• Maintains the integrity of the organization’s reputation by ensuring all safety-related board reporting is accurate, timely, and fully compliant with BPS guidelines
• Serves as the primary steward of executive and board-level confidentiality, ensuring that all sensitive information, strategic plans, and personal health data are handled with absolute discretion and in full compliance with PHIPA and BPS guidelines.
• Manages the secure flow of high-stakes information, implementing digital best practices for document encryption, password protection, and permission-based sharing to prevent unauthorized access to executive records.
• Exercises superior professional judgment and "executive presence" when navigating inquiries from internal and external stakeholders, skillfully protecting sensitive information without compromising key relationships.
• Safeguards the integrity of the board ecosystem by ensuring that all discussions, legal briefings, and sensitive minutes are captured, stored, and distributed through secure, authorized channels only.
• Proactively audits and optimizes administrative privacy protocols within the CEO’s office, identifying potential vulnerabilities in communication workflows and implementing corrective measures to ensure a "leak-proof" environment.

Benefits

• generous paid time off for vacation, personal and sick days.
• A robust benefits plan with comprehensive health, dental, paramedical and vision coverage with employer paid premiums to support you and your family through all stages of life.
• As part of our commitment to your long-term well-being, we provide an RRSP program through RBC with employer and voluntary employee contributions.
• We support your continued growth and learning through paid training and professional development opportunities throughout your career.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive