Executive Assistant in Winnipeg

Samsara (NYSE: IOT) is the pioneer of the Connected Operations™ Cloud, which enables organizations that depend on physical operations to harness Internet of Things (IoT) data to develop actionable insights and improve their operations. At Samsara, we are helping improve the safety, efficiency, and sustainability of the physical operations that power our global economy.

About the role: 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. You will master intricate calendaring, architect complex travel itineraries, oversee expense management, and drive high-profile team events.

This is a remote position based in Canada. Relocation assistance will not be provided for this role.

You should apply if:

• You want to impact the industries that run our world: Your efforts will result in real-world impact—helping to keep the lights on, get food into grocery stores, reduce emissions, and ensure workers return home safely.
• You are the architect of your own career: If you put in the work, this role won’t be your last at Samsara. We set up our employees for success and have built a culture that encourages rapid career development.
• You’re energized by our opportunity: The vision we have to digitize large sectors of the global economy requires your full focus and best efforts to bring forth creative, ambitious ideas for our customers.
• You want to be with the best: At Samsara, we win together, celebrate together, and support each other.

In this role, you will:

• 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 as we scale globally and across new offices.

Minimum requirements for the role:

• 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.

An ideal candidate also has:

• 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.

$82,025 — $106,150 CAD Total Rewards

At Samsara, we build for the people who keep the global economy moving. Our compensation program delivers above-market total compensation through a combination of base salary, performance-based bonus/variable pay, and equity (for eligible roles) in a high-growth public company.

Flexible Working: At Samsara, we embrace a flexible working model that caters to the diverse needs of our teams. Our goal is to ensure that all members of our team can contribute effectively, whether they are working on-site, in a hybrid model, or fully remotely.

Belonging at Samsara: We welcome everyone regardless of their background. All qualified applicants will receive consideration for employment without regard to race, color, religion, national origin, sex, gender, gender identity, sexual orientation, protected veteran status, disability, age, and other characteristics protected by law.

Accommodations: Samsara is an inclusive work environment, and we are committed to ensuring equal opportunity in employment for qualified persons with disabilities.