Executive Assistant to Managing Director
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Key skills for this role
Role Overview
The Executive Assistant closes the Managing Director’s administrative loop across two law firms and related ventures.
The role supports business priorities, personal scheduling, financial organization, and day-to-day follow-through.
The position is active and fast-paced, with changing priorities and significant responsibility.
Key Skills for This Role
Full Job Posting
Role Overview
The Executive Assistant closes the Managing Director’s administrative loop across two law firms and related ventures.
The role supports business priorities, personal scheduling, financial organization, and day-to-day follow-through.
The position is active and fast-paced, with changing priorities and significant responsibility.
Calendar and Communication
- Manage and protect a heavily booked calendar across multiple businesses.
- Triage email, messages, and calls; draft replies, route matters, and escalate urgent issues.
- Manage WhatsApp Business accounts, routine enquiries, lead capture, and conversation organization.
- Prepare daily and meeting briefings.
Follow-Through and Logistics
- Track assigned tasks to completion, chase outstanding items, and escalate blockers.
- Maintain open-item lists, provide status reports, and circulate meeting actions.
- Book travel, coordinate events, manage registrations, and handle deadlines.
- Coordinate business and personal scheduling, errands, deliveries, and office logistics.
- Drive between offices, courts, and client meetings when required.
Financial and Business Support
- Handle expenses, receipts, reimbursements, and coordination with the bookkeeper.
- Track personal accounts, bills, subscriptions, payments, and financial records.
- Prepare monthly financial summaries and coordinate with accounting, banking, and insurance contacts.
- Prepare documents, presentations, correspondence, research, vendor comparisons, and process projects.
- Work with the Director of Operations and Case Management Lead on processes, systems, and scheduling.
What We’re Looking For
- Exceptional organization, follow-through, judgment, and resilience in a fast-moving environment.
- Strong written and verbal communication and professional email drafting ability.
- Absolute discretion with confidential client, business, personal, and financial information.
- Accuracy with numbers, records, bills, receipts, and expenses.
- Comfort with Microsoft 365 or Google Workspace, document management, WhatsApp Business, Clio, and other systems.
- Valid Ontario driver’s licence and reliable access to a vehicle.
- Availability to work in person in Scarborough, with occasional early, late, or off-hours work.
- Post-secondary education in a relevant field or equivalent practical experience.
- Senior executive, business owner, or lawyer support experience is an asset.
- Willingness to sign a confidentiality agreement and complete a background check.
Workplace
- Work is performed in person from the Scarborough office.
- Driving between offices, courts, and client meetings is a real part of the role.
Compensation and Benefits
- Pay is $45,000 to $55,000 per year.
- Benefits include mileage reimbursement, on-site parking, and paid time off.
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