Executive Assistant & Canada Office Coordinator

OUR MISSION At Redwood, we empower our customers with lights-out automation for their mission-critical business processes. ABOUT US 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. 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 best-in-class physical workspace, and providing high-impact executive support to 3-4 members of our Executive Leadership Team (ELT). You will be the on-the-ground force that brings our Markham office to life — establishing culture, coordinating the day-to-day, 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. 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. This is a high-impact, high-trust role for someone who is deeply organized, proactive, and energized by variety. 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 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 fast-paced technology or SaaS environment. Bachelor’s degree in Business Administration, Communications, or a related field. Demonstrated experience managing complex, multi-stakeholder 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 high-quality 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. Self-starter 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, remote-first organization where communication, autonomy, and clarity are critical. 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. Background in helping stand up or scale a new office location. Experience coordinating events, offsites, or company-wide meetings at scale. WHY REDWOOD This is a rare opportunity to put your fingerprints on something new. You will not be inheriting an established office — you will be building one. 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. We are a company that moves fast, values curiosity, and believes in giving people the autonomy to own their outcomes. 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. 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. Vacancy Status: Existing vacancy AI Transparency Disclosure: As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI-enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; all final hiring and selection decisions are made exclusively by individuals on the hiring team. If you like growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us! 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 [email protected]