Executive Assistant, Chief Technology, Data & AI Officer

Healthcare of Ontario Pension Plan Trust Fund · Toronto · CA$71,000–CA$110,000 (stated in the posting)

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Why you’ll love working here:

• high-performance, people-focused culture

• our commitment that equity, diversity, and inclusion are fundamental to our work environment and business success, which helps employees feel valued and empowered to be their authentic selves

• learning and development initiatives, including workshops, Speaker Series events and access to LinkedIn Learning, that support employees’ career growth

• membership in HOOPP’s world class defined benefit pension plan, which can serve as an important part of your retirement security

• competitive, 100% company-paid extended health and dental benefits for permanent employees, including coverage supporting our team's diversity and mental health (e.g., gender affirmation, fertility and drug treatment, psychological support benefits of $2,500 per year, parental leave top-up, and a health spending account).

• optional post-retirement health and dental benefits subsidized at 50%

• yoga classes, meditation workshops, nutritional consultations, and wellness seminars

• the opportunity to make a difference and help take care of those who care for us, by providing a financially secure retirement for Ontario healthcare workers

Job Summary

The Executive Assistant (“EA”) plays an important role in supporting the Chief Technology, Data & AI Officer (CTDAIO) and the day-to-day operation of the Information Technology Division. Reporting directly to the CTDAIO, the EA provides proactive administrative and operational support and works closely with the IT leadership team.

This role goes beyond day-to-day executive support. The EA will help the CTDAIO stay organized and focused across priorities related to technology, data, AI, cybersecurity, talent, and transformation. The successful candidate will anticipate what is needed, take ownership, use good judgment, and follow through on decisions and commitments.

What you will do:

Note: This role is required to work in the office full-time.

Executive & Divisional Support

• Provide administrative support to the CTDAIO, including calendar management, meeting coordination, travel arrangements, correspondence, and preparation for executive, Board, committee, and divisional commitments.
• Manage competing priorities and use good judgment to protect the CTDAIO’s time and keep attention focused on the most important issues.
• Anticipate deadlines, decisions, dependencies, and potential issues; address what can be resolved independently and raise matters that require the CTDAIO’s attention.
• Work with the IT leadership team and partners across the organization to clarify owners, actions, and timelines and follow up on commitments.
• Prepare clear, accurate, and well-formatted materials to support decision-making.

Leadership Meetings & Follow-Through

• Support the CTDAIO’s executive, Board, committee, and IT leadership responsibilities by coordinating schedules, agendas, materials, pre-reads, decisions, and follow-up.
• Prepare and circulate meeting notes when needed, clearly capturing decisions, owners, timelines, and dependencies.
• Track priorities and commitments, follow up to keep work moving, and flag items that are delayed or at risk.
• Maintain executive and governance records in line with confidentiality, audit, and documentation requirements.
• Work closely with Executive Assistants, committee secretaries, and partners across the organization to coordinate schedules, materials, and follow-up.

Expense and Administrative Support

• Process invoices, expense claims, purchase documentation, and payments accurately and on time.
• Track deadlines and follow up on missing information or approvals to keep administrative work on schedule.

Events, Engagement & Coordination

• Coordinate IT leadership meetings, divisional calls, town halls, offsites, training sessions, and events, managing logistics and follow-up from start to finish.
• Coordinate leadership updates, key messages, presentations, and opportunities to share team progress and innovation across the division.
• Support activities that encourage ownership, accountability, collaboration, open communication, and continuous improvement.
• Partner with other Executive Assistants and teams across the organization on shared initiatives, events, and executive priorities.

Relationship Management & Collaboration

• Build strong working relationships with the CTDAIO, IT leaders, Executive Assistants, and stakeholders across the organization.
• Help ensure information is clear, accurate, timely, and shared with the right people.
• Use good judgment when handling sensitive issues and know when to act independently, seek input, or escalate.
• Communicate directly and constructively and help resolve coordination gaps before they cause delays.

Ways of Working & Continuous Improvement

• Handle confidential information with professionalism, discretion, and care.
• Bring a strong sense of ownership, urgency, and follow-through to a fast-paced and changing environment.
• Look for practical ways to simplify administrative processes and make work easier across the division.
• Use Microsoft 365, AI, automation, and other available tools appropriately to improve productivity, quality, and responsiveness.
• Contribute to a respectful, inclusive, and high-performing culture where expectations are clear and issues are addressed directly.

What you bring:

• University or college education, or equivalent experience.
• At least seven years of executive administrative experience, including direct support to a C-suite or similarly senior executive in a complex organization.
• Proven ability to manage complex calendars, competing priorities, executive meetings, confidential matters, and time-sensitive work with limited direction.
• Experience supporting executives, Board, committee, or senior leadership meetings, including coordinating agendas and materials, taking minutes, capturing decisions, and tracking actions.
• Experience with vendor administration, invoices, expense claims, purchase documentation, and related tracking.
• Advanced skills in Microsoft 365, including Outlook, Word, Excel, PowerPoint, Teams, and SharePoint. Experience using AI and automation tools is an asset.
• Strong organizational and prioritization skills, with the ability to manage several priorities while maintaining accuracy and follow-through.
• Excellent written and verbal communication skills, with the ability to prepare clear, accurate, and polished executive materials.
• A proactive and practical approach, with the confidence to take ownership, work independently, ask questions, and respectfully challenge when needed.
• Strong interpersonal skills and the ability to build effective relationships at all levels of the organization.
• Sound judgment and discretion when handling sensitive and confidential information.
• Adaptability, resilience, curiosity, and a commitment to continuous improvement.
• Alignment with HOOPP’s values with a commitment to an accountable, collaborative, respectful, and positive workplace.

The actual base salary offered to the successful candidate may vary based on multiple factors including, but not limited to, individual's expertise and level of experience applicable to the role they are being offered.  

This role is eligible to participate in discretionary incentive plan(s), subject to the terms and conditions of the applicable incentive plan text.  

HOOPP may use artificial intelligence tools to assist in screening, assessing and selecting applicants for this position. These tools support our recruitment process but do not replace human judgment and decision-making.

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