Executive Assistant to the Chief Operating Officer (AI)

Location: Toronto, Ontario, Canada; in-office a minimum of three days per week

Salary: CAD $110,000–$125,000 base salary annually, plus annual bonus and equity when applicable.

Company

hirify.global acquires, builds, and grows specialized software businesses worldwide, supporting more than 100 portfolio companies across North America, the UK, EU, and APAC.

What you will do

• Provide proactive executive support to the Chief Operating Officer, including complex calendar, travel, meeting, expense, and correspondence management.
• Coordinate priorities and dependencies across People, Legal, Corporate IT, Communications, Technology and Business Operations Centers of Excellence, and the hirify.global Foundation.
• Track OKRs, initiatives, action items, deadlines, and risks for the COO and her leadership team.
• Coordinate board meetings, quarterly business reviews, senior leadership meetings, functional deep dives, and leadership offsites.
• Prepare briefing materials, presentations, agendas, pre-reads, dashboards, and confidential communications.
• Apply AI tools to inbox triage, meeting preparation, note synthesis, drafting, dashboards, trackers, and repeatable workflow automation.

Requirements

• 5+ years of administrative experience supporting C-level executives in a fast-paced environment; COO or operational leadership support is strongly preferred.
• Experience managing complex calendars, executive meetings, events, presentations, expenses, board materials, quarterly reviews, and leadership offsites.
• Demonstrated daily use of AI tools such as Claude, ChatGPT, Copilot, or Gemini to improve or automate workflows.
• Advanced Microsoft Office skills, including executive-level presentations, graphs, tables, and charts; Slack, Google Workspace, and Notion experience is an asset.
• Strong written and interpersonal communication, executive presence, discretion, diplomacy, organization, autonomy, and judgment.
• Ability to work from the Toronto office at least three days per week.

Culture & Benefits

• Opportunity to work across a broad portfolio spanning corporate functions, operational centers of excellence, the executive leadership team, the board, and external partners.
• Permanent-capital, buy-and-hold-for-life operating model with more than 130 portfolio companies worldwide.
• Opportunity to shape scalable operating disciplines and develop deeper expertise across People, Legal, Technology, or the hirify.global Foundation.
• Annual bonus and equity may be available in addition to the base salary.
• Inclusive workplace committed to equal employment opportunities and accessibility.