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 Redwoods 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 (MondayFriday) 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 4055 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 Redwoods 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 Redwoods 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.

• Bachelors 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 dont 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 its 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 87175 - 99875 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 candidates 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.