Executive Assistant to the Chief Operating Officer (AI)

Location: Toronto, Ontario, Canada; hybrid, with a minimum of three days per week in the Toronto office, Tuesday through Thursday.

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

Company

Banyan Software acquires and grows specialized-industry software businesses through a permanent-capital, buy-and-hold-for-life model, operating more than 120 portfolio companies across the Americas, Europe, and APAC.

What you will do

• Provide proactive executive support to the Chief Operating Officer across People, Legal, Corporate IT, Communications, the Technology and Business Operations Centers of Excellence, and the Banyan Software Fouhirify.globaltion.
• Manage the COO’s calehirify.globalr, travel, meetings, correspondence, presentations, expenses, and confidential materials.
• Track the COO’s priorities, leadership-team OKRs, action items, deadlines, milestones, and risks across cross-functional workstreams.
• Coordinate board meetings, quarterly business reviews, senior leadership meetings, functional deep dives, leadership offsites, and related agehirify.globals, logistics, communications, and pre-reads.
• Maintain and improve operating templates, trackers, cadences, and processes while supporting accountability and progress visibility.
• Apply AI tools to inbox triage, meeting preparation, briefing materials, drafts, dashboards, trackers, note synthesis, and repeatable workflows, using judgment with confidential information.

Requirements

• 5+ years of administrative experience supporting C-level executives in a fast-paced environment; COO or operational leadership support is strongly preferred.
• Experience tracking company or functional goals such as OKRs or KPIs and moving cross-functional commitments forward without direct authority.
• Demonstrated daily use of AI tools such as Claude, ChatGPT, Copilot, Gemini, or similar, with examples of improved or automated workflows.
• Advanced Microsoft Office skills, including creating and refining executive-level presentations and building graphs, tables, and charts.
• Experience managing complex calehirify.globalrs, coordinating meetings and events, preparing presentations, and administering expense reports.
• Experience supporting board meetings, quarterly reviews, leadership offsites, materials management, and follow-through.
• Strong written and interpersonal communication, judgment, discretion, diplomacy, executive presence, and the ability to build trust with Board members and executive leaders.
• Ability to operate autonomously within agreed guardrails, make decisions, escalate appropriately, stay organized under pressure, and manage multiple tasks accurately.
• Collaborative, service-oriented approach with strong relationship-building skills, integrity, accountability, intellectual honesty, and proactive analytical problem-solving.

Nice to have

• Experience supporting COO or operational leadership.
• Experience with Slack, Google Workspace, and Notion.

Culture & Benefits

• Hybrid work arrangement requiring at least three days per week in the Toronto office.
• Opportunity to work across a broad portfolio spanning corporate functions, operating centers of excellence, the Fouhirify.globaltion, senior leadership, the CEO’s office, Board members, and external partners.
• Opportunity to extend existing AI tooling and shape scalable operating practices for the COO’s office.
• Potential annual bonus and equity in addition to base salary.
• Inclusive workplace committed to equal employment opportunities and accessibility.