Executive Assistant & Canada Office Coordinator

About the role

Redwood Software is the leader in full stack automation fabric solutions for mission-critical business processes. With the first SaaS-based composable automation platform specifically built for ERP, we believe in the transformative power of automation. Our solutions help thousands of organizations across 150 countries execute with speed and precision. We pride ourselves on having an inclusive, supportive, coaching culture, giving you the opportunity to build lasting relationships with all our team members and senior leadership. CORE VALUES One Team. One Redwood Make Your Own Weather Obsess over Customer Success Work the Problem Be Curious Own the Outcome Respect Each Other WORK ARRANGEMENT This is a hybrid role based out of our leased Markham, Ontario office (target opening date: July 2026). In alignment with Redwood's Canada In-Office Policy, the following schedule applies: Monday and Tuesday are mandatory in-office days for all GTA-based employees. Wednesday through Friday are flexible - work from the office or remotely based on team needs, project requirements, and personal preference. A monthly innovation and team-building day will be held in-office. All GTA-based employees are required to be in-office for one full week (Monday-Friday) each fiscal quarter. Dates are communicated at least four weeks in advance. Given the nature of this role - supporting multiple ELT members and serving as the operational anchor for the Markham office - additional in-office presence may be expected during leadership visits, executive offsites, and key planning periods. 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).
• Office Management (40% time)
• 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.
• Serve as the primary point of contact for all office-related matters - facilities, supplies, equipment, maintenance, and vendor relationships.
• Create a welcoming, functional, and well-organized work environment that reflects Redwood's culture and supports both on-site meetings and remote engagement.
• Plan and execute in-office employee engagement events, team meetings, all-hands gatherings, and culture moments that connect local employees to the broader global organization.
• 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.
• Act as a cultural ambassador - helping remote employees feel connected when they visit, and ensuring local employees feel part of One Redwood.
• Executive Assistance (60% time)
• Provide proactive, anticipatory calendar management for 3-4 ELT members, including one semi-local to the Greater Toronto Area and others based remotely.
• Coordinate complex, multi-party meeting scheduling across time zones, balancing competing priorities with professionalism and good judgment.
• 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.
• Coordinate logistics for leadership offsites and cross-functional executive sessions - including room booking, A/V, catering, and materials.
• Maintain organized dig

Benefits

Additional Information

OUR MISSION At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

Your Match

How well this role fits your profile.

Company Intel

What employees say

Worked at redwoodsoftware? Share your experience