Hybrid Executive Assistant & Canada Office Lead

Redwood Software; Markham; Hybrid; CAD 87,000 - 100,000; Full time

Job summary

Redwood Software is creating a Markham, Ontario office and seeks an experienced Office Manager / Executive Assistant to support ELT members and run the new Canadian hub.

You will manage calendars, travel, budgets, facilities, and cross-functional coordination, reporting to the Chief of Staff to the CEO. This hybrid role blends on-site office administration with executive support across time zones.

Qualifications

• 4+ years of combined experience in office management, executive assistance, or administrative operations.
• Bachelor’s degree in Business Administration, Communications, or a related field.
• Demonstrated ability to manage complex multi-stakeholder calendars and travel logistics across time zones.
• Proven ability to operate an office environment independently with vendor relationships and facilities operations.
• Exceptional organizational skills with the ability to juggle priorities and maintain high-quality output.
• Strong written and verbal communication skills and discretion when handling confidential information.

Responsibilities

• Office Management: support opening of the Markham office, coordinate with vendors and IT for readiness.
• Be primary contact for facilities, supplies, equipment, maintenance, and vendor relationships.
• Create a welcoming work environment and plan in-office engagement events and all-hands gatherings.
• Own office budgets, expense tracking, and invoice processing for facilities and operations.
• Executive Assistance: manage calendars for 3-4 ELT members across time zones.
• Coordinate complex multi-party meeting scheduling and travel arrangements internationally.
• Handle expense reports and onboarding experiences for visiting or local staff.
• Collaborate with EA teams in the US to share best practices and ensure high-quality support.

Skills

Calendar management

Travel coordination

Vendor management

Communication

Education

Bachelor’s degree

Tools

Google Workspace

Microsoft 365

Slack

Zoom

Job description

Redwood Software is creating a Markham, Ontario office and seeks an experienced Office Manager / Executive Assistant to support ELT members and run the new Canadian hub.

You will manage calendars, travel, budgets, facilities, and cross-functional coordination, reporting to the Chief of Staff to the CEO. This hybrid role blends on-site office administration with executive support across time zones.