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About the Role

The Personal Assistant to the Executive Team serves as a trusted and highly dependable extension of the Executive leadership, providing both executive and personal support to ensure seamless day-to-day operations. This role combines executive administration, personal assistance, and light operational coordination, requiring exceptional organization, discretion, initiative, and sound judgment. The ideal candidate is proactive, highly organized, and capable of anticipating needs before they arise, while maintaining absolute confidentiality and professionalism at all times. This is an active, on-site role based out of the Richmond Hill office.

Responsibilities

Manage calendars, appointments, meetings, and daily schedules for members of the Executive Team.
Coordinate meetings, including scheduling, agenda preparation, and distribution of supporting materials.
Arrange complex travel itineraries including flights, accommodations, transportation, and logistics.
Track action items from meetings and ensure timely follow-ups on deliverables.
Assist in preparing correspondence, presentations, reports, and confidential documents.
Coordinate and support special projects as assigned.
Act as a liaison between executives and internal/external stakeholders including employees, clients, vendors, and partners.
Organize and maintain executive offices and personal workspaces.
Manage personal calendars, appointments, and scheduling needs.
Handle personal errands such as dry cleaning, shopping, banking, courier services, gift purchases, prescription pickups, and vehicle servicing.
Coordinate home service providers as required.
Assist with personal travel arrangements and planning.
Purchase and manage both office and personal supplies.
Ensure executive vehicles are maintained, serviced, fueled, and available as needed.
Maintain structured digital and physical filing systems.
Prepare, process, and reconcile expense reports and receipts.
Track and manage invoices requiring approval.
Coordinate meetings, lunches, events, and reservations.
Maintain task lists, trackers, and executive dashboards where applicable.
Support and manage small to medium-sized projects across the executive office.
Track project milestones, timelines, dependencies, and risks.
Prepare regular status updates and reports for the Executive Team.
Maintain organized and efficient executive office environments.
Coordinate office maintenance, hospitality, and vendor relationships.
Ensure office supplies and essentials are stocked and managed.
Support planning and execution of executive meetings, conferences, dinners, and corporate events.
Coordinate logistics, vendors, invitations, and on-site arrangements when required.

Requirements

College diploma or university degree preferred.
3–5 years of experience in an Executive Assistant, Personal Assistant, or similar support role.
Prior experience supporting senior executives is highly preferred.
Valid Ontario driver’s licence and access to reliable transportation.
Exceptional organizational and time management abilities.
Strong verbal and written communication skills.
Proficiency in Microsoft 365 and Google Workspace.
Ability to quickly learn and adapt to new technologies.
High attention to detail and accuracy.
Integrity and absolute discretion.
Professionalism in all interactions.
Initiative and strong sense of ownership.
Resourcefulness and problem-solving mindset.
Strong work ethic and reliability.
High emotional intelligence.
Flexibility and adaptability in dynamic environments.
Ability to anticipate needs proactively.
Ability to lift packages up to approximately 25 lbs (11 kg).
Comfortable driving within the Greater Toronto Area.
Occasional evening or weekend availability as required.

Skills

Microsoft 365
Google Workspace

Location

Richmond Hill

Work Type

On-site

Experience Level

3-5 years

Education Level

College diploma or university degree preferred

Salary/Compensations

Competitive compensation package

Benefits

Opportunities to expand knowledge and develop broader business operations expertise
Potential to grow into supporting additional teams, functions, and strategic initiatives across the organization
Supportive work environment with a focus on safety and innovation

About the Company

Umbrella Incorporated partners with enterprises to navigate complexity, accelerate growth, and drive measurable impact.
This role will support both Cloud Managed Networks and Tidal Commerce, two member companies of Umbrella Incorporated, supporting a dynamic and growing environment spanning IT infrastructure, cloud technologies, cybersecurity, and digital commerce consulting & implementation.

Equal Opportunity

Umbrella Inc is committed to creating and maintaining a workplace that is free from harassment and discrimination under the Ontario Human Rights Code.
The Company’s policy is not to discriminate against any applicant or employee on the basis of a prohibited ground enumerated by the Ontario Human Rights Code.
Umbrella welcomes and encourages applications from people with disabilities.
Accommodations are available on request for candidates taking part in all aspects of the selection process.
Please advise Human Resources if you require accommodation.
Further, it is Umbrella's policy to comply with all applicable provincial and federal laws regarding background and criminal record checks in making hiring decisions.