Executive Assistant (AI)

Location: Based in Kitchener or Winnipeg, Ontario/Manitoba, Canada, with at least three days per week in the office

Salary: CAD 75,000–85,000 annual base salary

Company

hirify.global is a cloud education technology company building learning environments and solutions that modernize teaching, learning, and the future of work.

What you will do

• Support the CPO and CTO by managing integrated calendars, priorities, meeting agendas, pre-reads, decisions, actions, and follow-through.
• Manage executive information flow, triage requests, draft responses, track commitments, and surface unresolved decisions and risks.
• Draft and edit executive communications, leadership updates, presentations, talking points, executive-team materials, and Board materials.
• Coordinate planning, leadership routines, offsites, events, team sessions, hiring, onboarding, and organization-transition activities across Product and TED.
• Coordinate travel, expenses, budgets, spending commitments, approvals, and budget-review inputs with FP&A.
• Improve executive workflows and use approved AI tools, including ChatGPT and Rovo, for preparation, drafting, meeting synthesis, research, and action tracking.

Requirements

• At least three years of experience supporting senior leaders as an Executive Assistant, executive coordinator, or in a comparable high-trust role within a fast-paced organization.
• Excellent written communication skills and the ability to turn incomplete inputs into clear, concise, well-structured materials.
• Strong organizational discipline, attention to detail, and the ability to manage multiple priorities.
• Exceptional judgment, discretion, and confidence to respectfully push back, ask clarifying questions, and protect executive capacity.
• Proactive approach to anticipating needs, identifying gaps, and proposing solutions.
• Strong relationship-building skills and comfort working with technical and non-technical leaders.
• Confidence with modern productivity tools and practical experience using AI tools to improve work quality and speed.
• Comfort operating amid ambiguity and changing priorities with a calm, reliable approach.

Culture & Benefits

• Hybrid work with at least three office days per week; office locations for this role are Kitchener or Winnipeg.
• Learning and growth opportunities, including tuition reimbursement of up to CAD 4,000 through the SkillsWave Program and two paid days for related activities.
• Employee wellbeing support, including mental health services, an EFAP program, financial planning, retirement planning, and competitive benefits.
• Two paid volunteer days, home internet reimbursement, wellness reimbursement, employee recognition, and referral programs.
• Flexible work arrangements, social events, and dog-friendly offices.