Redwood Software

Executive Assistant & Canada Office Coordinator

Ontario, Canada

Sponsorship not specified$87k-$100kDetected 1 day ago

Data EngineeringAgentic AIComplianceLogisticsERPRecruitingHRISCustomer SuccessLeadershipCommunicationCollaborationOrganizational Skills

About the role

Through its SaaS-first automation fabric-with AI embedded across the automation lifecycle-Redwood accelerates the path to autonomous operations.
Dates are communicated at least four weeks in advance.
Flexibility to be on-site when it matters most is essential to success in this position.

Responsibilities

As Redwood opens its first Canadian office in Markham, Ontario, this newly created role sits at the intersection of two critical functions: launching and running a best-in-class physical workspace, and providing high-impact executive support to 3-4 members of our Executive Leadership Team (ELT).
Simultaneously, you will operate as a trusted executive partner, keeping senior leaders organized, on time, and focused on what matters most.
You will collaborate closely with two other EAs (based in Florida and Virginia) to ensure consistent, high-quality executive support, and you will report to the Chief of Staff to the CEO.
Support all activities related to the opening of our leased Markham office, including coordinating with vendors, building management, and IT to ensure readiness for a July 2026 launch - target headcount of 40-55 employees by end of year.
Own office budgets, expense tracking, and invoice processing related to facilities and operational needs.
Establish and maintain office policies, procedures, and safety protocols in compliance with local regulations and Redwood's global standards.
Partner with IT, HR/People, and Finance to support seamless onboarding experiences for new hires based in or visiting the Markham office.
Manage relationships with building management, security, cleaning services, and other local service providers.
Manage end-to-end domestic and international travel arrangements including flights, accommodations, ground transportation, visa/entry requirements, and detailed travel itineraries.
Own expense management - accurately processing and submitting expense reports and ensuring timely reconciliation for supported executives.

Requirements

All GTA-based employees are required to be in-office for one full week (Monday-Friday) each fiscal quarter.

Nice to have

Experience leveraging AI tools (e.g., ChatGPT, Claude, or similar) to automate repetitive tasks, streamline workflows, or surface insights.
Experience supporting C-suite or senior ELT executives in a global organization.
Familiarity with Greenhouse, Workday, or similar HR/ATS platforms.
Experience coordinating events, offsites, or company-wide meetings at scale.
This is a rare opportunity to put your fingerprints on something new.
From day one, you will have a direct line to senior leadership, genuine ownership of your work, and the ability to shape how Redwood shows up in Canada.
If you thrive in environments where no two days are the same, where your contributions are visible, and where "it's not my job" is not in your vocabulary - you will find a home here.
Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.

Skills

Redwood is an equal opportunity employer.
All such discrimination is unlawful and will have a zero tolerance policy applied to it.
Redwood will comply with all local data protection laws, including GDPR when it comes to the handling and processing of personal data.
Should you wish for us to remove your personal data from our recruitment database, please email us directly at Recruitment@Redwood.com

Compensation

The typical base salary range for this position is 87,175 - 99,875 CAD annually.
The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable.
Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.

Benefits

The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable.

Company info

Redwood Software is the leading orchestration platform for the autonomous enterprise, driving business transformation at the lowest total cost of ownership. Redwood empowers organizations to intelligently automate and orchestrate mission-critical business and IT processes across complex ERP, hybrid cloud, data and emerging agentic AI systems. Through its SaaS-first automation fabric-with AI embedded across the automation lifecycle-Redwood accelerates the path to autonomous operations. Backed by 30 years of experience and trusted by more than 50% of the Fortune 50, Redwood helps organizations unlock human potential to focus on innovation, growth and what's next.
One Team. One Redwood
Make Your Own Weather
Obsess over Customer Success
This is a hybrid role based out of our leased
At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.
Redwood Software is the leading orchestration platform for the autonomous enterprise, driving business transformation at the lowest total cost of ownership.
Redwood empowers organizations to intelligently automate and orchestrate mission-critical business and IT processes across complex ERP, hybrid cloud, data and emerging agentic AI systems.
Backed by 30 years of experience and trusted by more than 50% of the Fortune 50, Redwood helps organizations unlock human potential to focus on innovation, growth and what's next.
Work the Problem
Own the Outcome
Respect Each Other
This is a hybrid role based out of our leased Markham, Ontario office (target opening date: July 2026).

Visa & Work Authorization

Manage end-to-end domestic and international travel arrangements including flights, accommodations, ground transportation, visa/entry requirements, and detailed travel itineraries.

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This listing is sourced directly from Redwood Software's careers page and normalized into a canonical job model.