Executive Assistant

Remote · Toronto · CAD 82,025-106,150 / year · 3+ years experience · Remote · Posted Oct 19, 2026

At a glance

Are you an exceptionally agile, strategic, and execution-focused Executive Assistant ready to power high-growth leadership?
In this high-impact, dynamic role, you will serve as the strategic operational backbone and trusted partner to 3 Area Vice Presidents across our fast-paced Sales organization.

Serve as an Executive Ambassador: Represent your 3 Area VPs with polish and diplomacy across key external partners, high-profile clients, and internal department stakeholders.
Drive Calendar Strategy: Proactively optimize, align, and defend complex schedules across multiple Sales leaders to maximize business momentum and executive focus.
Master Logistics & Travel: Design and book multi-leg travel itineraries, anticipating seamlessly for potential schedule changes and travel logistics.
Manage Business Expenses: Oversee, track, and streamline expense reporting and reconciliations with high accuracy.
Orchestrate Staff Meetings: Partner with leadership to curate agendas, prepare materials, and track key deliverables for departmental meetings.
Lead Event Planning: Plan, coordinate, and execute impactful team offsites, strategy summits, and team-building events that drive culture and connection.
Anticipate & Resolve: Stay ten steps ahead by anticipating executive needs, eliminating friction, and tackling shifting business priorities with urgency.
Execute Strategic Projects: Own ad-hoc administrative initiatives and operational projects to increase overall leadership efficiency.
Champion Culture: Champion, role model, and embed Samsara’s cultural principles (Focus on Customer Success, Build for the Long Term, Adopt a Growth Mindset, Be Inclusive, Win as a Team) as we scale globally and across new offices

3+ years of executive administrative experience directly supporting executives in a fast-paced corporate environment.
Proven track record of managing complex, multi-executive calendars, travel logistics, and shifting priorities with exceptional accuracy and composure.
Superior written and verbal communication skills, with high emotional intelligence and executive presence across all internal and external touchpoints.
Demonstrated discretion and sound judgment when handling highly sensitive company information and business scenarios.

Prior experience supporting high-growth Sales leadership within a SaaS or enterprise technology company.
Proficiency with AI productivity tools and modern enterprise workflow technology to enhance administrative efficiency.