Executive Assistant to the Chief Strategy

Executive Assistant to the Chief Strategy & Innovation Officer For accessibility assistance with this document please telephone Elections Ontario at 1- or Fax at 1-. You can TTY at 1- or via email at . Position Status: Permanent Posting Status: Open Location: 26 Prince Andrew Place, Toronto, Ontario M3C 2H4 (Don Mills and Eglinton) Salary Band: $73,531 to $102,803 per annum Hours of Work : 36.25 per week Posting Date: January 8, 2026 Closing Date: January 15, 2026 The Opportunity Elections Ontario is seeking a highly capable, forward-thinking Executive Assistant to support the Chief Strategy and Innovation Officer (CSIO) at a pivotal moment in the organization's evolution. This role goes beyond traditional executive assistance. It is designed for someone who operates as a strategic extension of an executive leader - anticipating what's coming, preparing for decisions before they are asked for, and helping translate strategy into action across the organization. You will sit at the centre of Election Ontario's (EO's) transformation agenda, supporting enterprise planning, cross-division coordination, and executive decision-making. The successful candidate will bring the mindset, judgment, and curiosity often associated with the Chief of Staff. This is an opportunity for a high-potential individual who thrives in complexity, learns quickly, and wants exposure to how strategy, governance, and execution come together at the enterprise level. What you will do Executive Enablement & Anticipation You will act as a force multiplier for the Chief Strategy and Innovation Officer (CSIO), ensuring they are prepared, informed, and positioned to lead effectively. Anticipate the CSIO's needs by preparing agendas, materials, briefings, and decision notes in advance. Manage the CSIO's calendar and commitments strategically prioritizing time against enterprise impact. Prepare the CSIO for meetings by synthesizing context, surfacing risks, and highlighting decisions required. Track commitments, follow-ups, and actions across meetings to ensure momentum and accountability. Exercise sound judgment in handling sensitive matters with discretion and professionalism. Cross-Division Coordination & Influence Serve as a trusted liaison between the CSIO, Directors, and senior leaders across EO. Coordinate inputs, materials, and timelines across teams to support executive decision-making. Build strong working relationships based on trust, clarity, and follow-through. Represent the CSIO professionally in interactions where appropriate, ensuring consistency and confidence. Operating Excellence & Judgment You will bring structure, discipline, and clarity to a complex and fast-moving environment. Design and maintain simple systems to track priorities, decisions, and deliverables. Identify opportunities to improve how workflows across the portfolio. Know when to escalate issues, when to resolve independently, and when to seek clarity. Uphold Elections Ontario's values and contribute to a respectful, collaborative workplace culture. What We're Looking For This role is best suited to someone who thinks beyond tasks and operates with ownership. Capabilities & Experience Minimum 5 years experience as an Executive Assistant supporting senior Management. Exceptional organizational, written, and verbal communication skills. Strong judgment and discretion in handling sensitive or ambiguous situations. Ability to synthesize complex information into clear, actionable insights. Comfort working independently while staying tightly aligned with an executive leader. Experience supporting senior leaders or complex initiatives is an asset. Mindset & Attributes A proactive, anticipatory mindset, you think several steps ahead. High learning agility: you absorb new concepts quickly and apply them confidently. A systems thinker who sees connections across teams, priorities, and timelines. Calm, reliable, and composed under pressure. Comfortable engaging with senior leaders and navigating complexity with confidence. Values & Fit A strong interest in Elections Ontario's mandate and public service impact. Thrives in environments experiencing change and transformation. Takes pride in preparation, follow-through, and enabling others to succeed. Brings a growth mindset and a desire to continuously improve how work gets done. Must be legally entitled to work in Canada. Why This Role Matters This role is critical to enabling the work of the CSIO and supporting EO's shift toward an 'Always Ready' organization. You will gain exposure to enterprise strategy, planning, governance, execution and play a meaningful role in how EO prepares to deliver elections in a more complex and dynamic environment. How to apply Our recruitment process reflects our mission to uphold the integrity and accessibility of the electoral process and to manage elections in an efficient, fair, and impartial manner. We offer career growth opportunities and a competitive rewards program. Please submit your cover letter and resume as one attachment, quoting File #EO- in the subject line, to no later than January 15, 2026. We thank all applicants for their submission. Only those candidates selected for an interview will be contacted. How to request an accommodation Elections Ontario is an equal opportunity employer. We are committed to fostering an inclusive, equitable and accessible environment, where all employees feel valued, respected, and supported. Under the Accessibility for Ontarians with Disabilities Act and the Ontario Human Rights Code, we provide accommodations to applicants with disabilities throughout the recruitment and selection process. If you require a disability-related accommodation to participate, please call 1-, send a fax to 1-, TTY at 1- or email .