Executive Assistant & Canada Office Coordinator

Redwood Software

2d•Hybrid

About The Position

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.

Requirements

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 Haves

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.

Responsibilities

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.
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.