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Job Title


Executive Assistant & Canada Office Coordinator Ontario, Canada


Company : Redwood


Location : Markham,


Created : 2026-05-02


Job Type : Full Time


Job Description

Executive Assistant & Canada Office Coordinator OUR MISSION: At Redwood, we empower our customers with lightsout automation for their missioncritical business processes. ABOUT US: Redwood Software is the leader in full stack automation fabric solutions for missioncritical business processes. With the first SaaSbased 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. 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). Monday and Tuesday are mandatory inoffice days for all GTAbased 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 teambuilding day will be held inoffice. All GTAbased employees are required to be inoffice for one full week each fiscal quarter. Additional inoffice presence may be expected during leadership visits, executive offsites, and key planning periods. YOUR IMPACT 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 bestinclass physical workspace, and providing highimpact executive support to 3-4 members of our Executive Leadership Team (ELT). You will be the onground force that brings our Markham office to life establishing culture, coordinating the daytoday, and making sure local team members have everything they need to do their best work. Simultaneously, you will operate as a trusted executive partner, keeping senior leaders organized, on time, and focused on what matters most. 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 4055 employees by end of year. Serve as the primary point of contact for all officerelated matters facilities, supplies, equipment, maintenance, and vendor relationships. Create a welcoming, functional, and wellorganized work environment that reflects Redwood''s culture and supports both onsite meetings and remote engagement. Plan and execute inoffice employee engagement events, team meetings, allhands 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 semilocal to the Greater Toronto Area and others based remotely. Coordinate complex, multiparty meeting scheduling across time zones, balancing competing priorities with professionalism and good judgment. Manage endtoend 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 crossfunctional executive sessions including room booking, A/V, catering, and materials. Maintain organized digital filing systems, shared drives, and reference documents for ELT members. Collaborate with the EA team in the US to share best practices, align on processes, and cover for one another as needed. Handle sensitive and confidential information with complete discretion and professionalism at all times. YOUR EXPERIENCE 4+ years of combined experience in office management, executive assistance, or administrative operations, ideally within a fastpaced technology or SaaS environment. Bachelors degree in Business Administration, Communications, or a related field. Demonstrated experience managing complex, multistakeholder calendars and travel logistics across time zones. Proven ability to manage an office environment independently from vendor relationships to facilities operations to employee engagement. Exceptional organizational skills with the ability to juggle multiple priorities, adapt to shifting demands, and maintain highquality output under pressure. Strong written and verbal communication skills; comfortable drafting executive communications and interfacing with senior leaders. High degree of discretion and integrity when handling confidential information. Proficiency with modern productivity and collaboration tools including Google Workspace or Microsoft 365, Slack, Zoom, and expense management platforms. Selfstarter mindset with a bias for action you don''t wait to be asked, you anticipate needs and move forward with confidence. Comfortable operating in a global, remotefirst organization where communication, autonomy, and clarity are critical. Nice to Have Experience leveraging AI tools (e.g., ChatGPT or similar) to automate repetitive tasks, streamline workflows, or surface insights. Experience supporting Csuite or senior ELT executives in a global organization. Familiarity with Greenhouse, Workday, or similar HR/ATS platforms. Background in helping stand up or scale a new office location. Experience coordinating events, offsites, or companywide meetings at scale. Pay Transparency 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. THE LEGAL BIT Redwood is an equal opportunity employer. Redwood prohibits unlawful discrimination based on race, colour, religion, sex, gender identity, marital or veteran status, age, national origin, ancestry, citizenship, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member), sexual orientation, pregnancy or any other consideration made unlawful by regional or local laws. We also prohibit discrimination based on a perception that anyone has any of those characteristics or is associated with a person who has or is perceived as having any of those characteristics. 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 #J-18808-Ljbffr