Operating Assistant Jobs in Markham, ON (NOW HIRING)

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The Executive Assistant provides high-trust, proactive executive support to the Vice-President, Digital Product. This role is responsible for managing the VP's operating rhythm, calendar, priorities, communications, travel, meetings, and administrative workflows with a high degree of judgment, discretion, and professionalism.

The ideal candidate is highly organized, digitally fluent, calm under pressure, and able to anticipate needs, manage ambiguity, and build strong relationships across senior leadership, cross-functional teams, and external partners. They are comfortable working in a dynamic, high-energy digital product environment and are open to using AI and emerging tools to improve productivity, coordination, and ways of working

Responsibilities:

• Own complex calendar management for the VP, proactively optimizing time against business priorities, executive commitments, decision forums, and urgent operational needs.
• Triage emails, requests, and inbound priorities with sound judgment, escalating urgent or sensitive matters and ensuring timely follow-up.
• Support the VP's leadership operating rhythm, including leadership team meetings, business reviews, product reviews, steering committees, offsites, and follow-up on key actions.
• Organize meetings end to end, including planning, agendas, scheduling, room/technology setup, materials, notes, and action-item tracking.
• Build and maintain trusted working relationships with executive offices, senior leaders, assistants, leadership teams, external partners, and cross-functional stakeholders.
• Represent the VP's office with professionalism, discretion, responsiveness, and strong service orientation.
• Support a digital product organization operating across commercial, customer, airport, operational, and technology domains, with curiosity and comfort working in a technology-enabled, customer-focused environment.
• Prepare, format, and polish executive-ready presentations, briefing materials, agendas, reports, and meeting packages.
• Use Microsoft 365, collaboration platforms, AI-enabled tools, and other digital solutions to improve administrative workflows, coordination, and team effectiveness.
• Coordinate travel arrangements, including flights, hotels, ground transportation, meals, itineraries, and related logistics.
• Complete and manage expense reports, invoices, purchase orders, and other administrative processes accurately and on time.
• Support budget administration activities, including invoice tracking, expense reporting, accruals, and coordination with Finance, as required.
• Maintain accurate records, files, contact lists, distribution lists, and shared information repositories.
• Handle confidential, sensitive, and time-critical information with discretion, maturity, and sound judgment.
• Proactively follow up with team members and stakeholders to ensure commitments, deliverables, and action items are completed in a timely manner.
• Support special projects, team events, offsites, communications, onboarding activities, and ad hoc initiatives that improve the effectiveness of the VP's office and leadership team.
• Administer telecommunications and related branch services, including coordination with providers, IT, mobile device requests, and invoice monitoring.
• Perform other duties as assigned.

Qualifications

• College or university degree, or equivalent combination of education and experience.
• 5+ years of experience providing administrative or executive support to senior leaders, preferably in a large, complex, matrixed organization.
• Proven ability to manage a senior executive's calendar, priorities, communications, and confidential information with discretion and sound judgment.
• Strong business acumen and ability to understand executive priorities, organizational dynamics, and stakeholder sensitivities.
• Excellent organizational skills, with strong attention to detail and the ability to manage multiple priorities under tight timelines.
• Strong interpersonal skills, with a collaborative, customer-focused, and solutions-oriented approach.
• Exceptional written and verbal communication skills, including the ability to draft clear, professional correspondence and prepare executive-ready materials.
• Advanced proficiency with Microsoft 365, including Outlook, PowerPoint, Excel, Word, Teams, SharePoint, and collaboration tools.
• Digitally savvy, curious, and comfortable adopting AI, automation, and modern workplace tools to improve productivity, communication, and coordination.
• Able to thrive in a dynamic, collaborative, fast-moving team environment with shifting priorities, diverse working styles, and a strong bias for action.
• Able to work independently, exercise initiative, solve problems, and maintain composure in a dynamic, fast-paced environment.
• High degree of diplomacy, discretion, professional maturity, and judgment.
• Bilingualism in English and French is an asset.
• Flexibility and willingness to work extended hours on occasion.
• Occasional travel may be required.

Conditions of Employment:

Candidates must be eligible to work in the country of interest at the time any offer of employment is made and are responsible for obtaining any required work permits, visas, or other authorizations necessary for employment. Prior to their start date, candidates will also need to provide proof of their eligibility to work in the country of interest.

Linguistic Requirements

Based on equal qualifications, preference will be given to bilingual candidates.

Diversity and Inclusion

Air Canada is strongly committed to Diversity and Inclusion and aims to create a healthy, accessible and rewarding work environment which highlights employees' unique contributions to our company's success.

As an equal opportunity employer, we welcome applications from all to help us build a diverse workforce which reflects the diversity of our customers, and communities, in which we live and serve.

Air Canada thanks all candidates for their interest; however only those selected to continue in the process will be contacted.