We're looking for an Executive Assistant to join our team on a temporary basis. You'll provide day-to-day administrative support to our CEO, helping manage their schedule, communications, travel, and administrative priorities so they can stay focused on leading the business. This is a great opportunity for someone early in their career who is organized, dependable, proactive, and eager to learn. This is a fixed-term contract position expected to last 14 months, with the possibility of extension.

Responsibilities

Manage and coordinate the CEO's calendar, balancing scheduling requests and competing priorities

Coordinate internal and external meetings, including scheduling and logistics

Organize travel arrangements, including flights, accommodations, itineraries, and travel logistics

Prepare, format, and proofread documents, presentations, and correspondence

Monitor and triage the CEO's inbox, responding or escalating messages as appropriate

Take meeting notes and follow up on action items as needed

Complete and submit expense reports using Expensify

Serve as a professional point of contact for internal and external stakeholders on behalf of the CEO

Order office supplies and help coordinate office logistics

Support the planning and coordination of internal events and meetings

Perform other general administrative duties as assigned

Qualifications & Skills Required

High school diploma or equivalent; post-secondary education is an asset

3+ years of experience as an Executive Assistant or in an administrative or office support role

Strong organizational skills and attention to detail

Excellent written and verbal communication skills

Proficiency with Google Workspace (Calendar, Gmail, Docs, Sheets, and Slides)

Ability to prioritize effectively and adapt as priorities shift in a dynamic startup environment





Discretion and professionalism when handling confidential information

Nice to Have

Experience supporting an executive or leadership team

Experience coordinating travel and scheduling

Familiarity with expense reporting tools

Comfortable using AI tools (such as Claude, ChatGPT or similar) to improve productivity and streamline administrative tasks

Experience working in a startup or fast-paced environment

You’ll Thrive Here If

You're organized and enjoy keeping things running smoothly behind the scenes

You take initiative and follow through with minimal supervision

You're comfortable navigating ambiguity and adjusting as priorities evolve

You're curious, resourceful, and comfortable asking questions and learning as you go

What’s In It For You

Competitive compensation, commensurate with experience

Comprehensive health benefits for you and your family, including dental, extended health, vision care, and a health spending account - at no cost to you

The opportunity to work closely with executive leadership and gain firsthand exposure to how a growing company operates

A collaborative, fast-paced environment where your organization and initiative make a visible impact

Hybrid work arrangement based in Edmonton, AB

Samdesk is an equal opportunity employer committed to creating a safe, diverse and inclusive setting. We encourage qualified applicants of all backgrounds including ethnicity, religion, disability status, gender identity, sexual orientation, family status, age, nationality, and education levels to apply. If you are contacted for an interview and require accommodation during the interviewing process, please let us know.

The position is based out of Edmonton, AB. Please note that only candidates selected for the interview process will be contacted. Thank you!

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📌 Executive Assistant (Winnipeg)
🏢 samdesk
📍 Winnipeg