Role Summary
We are seeking a highly organized Executive Operations Specialist to support our Founder and CEO to manage programs, events, and operational initiatives. This role is approximately 50% executive assistant support (calendar, scheduling, travel, correspondence, personal tasks) and 50% operations coordination (program support, events, projects).
This is a full-time annual contract role for someone who thrives on detail and precision while also enjoying variety and project coordination.
Key Responsibilities
Executive Assistant (50%)
- Manage and optimize the Founder’s calendar.
- Schedule meetings, events, and personal appointments.
- Coordinate all travel logistics and prepare detailed itineraries.
- Draft and manage correspondence with discretion.
- Provide personal support for household/vendor tasks and odd projects.
Operations & Events (50%)
- Coordinate track member participation, manage communications, and ensure a positive member experience.
- Plan and coordinate events — virtual sessions, retreats, summits, and speaking engagements.
- Remotely manage logistics for in-person events, including vendors, venues, and partners.
- Liaise with contractors, faculty, and external partners to ensure smooth execution.
- Maintain systems for documentation, contracts, and workflows.
- Track deliverables and follow up with stakeholders.
Requirements
- 7–10+ years of experience in Executive Assistant, Operations, or hybrid EA/Ops roles.
- Strong project management skills; able to plan, track, and deliver projects.
- Excellent organizational and communication skills.
- Experience in event planning and coordination (including in-person events).
- Proficiency with tools such as Google Workspace, Slack, Zoom, and project management platforms (e.g., Asana, Trello, Monday.com).
- Professional, discreet, and proactive — able to handle sensitive information.
- Adaptable and resourceful; thrives in fast-paced, shifting environments.
- Background in wellness, education, or coaching industries is a plus.
Compensation & Contract
- Contract Type: Full-time annual contract (remote, preference for Canada-based candidates)
- Hourly Rate: $35–$50 CAD/hour (approx. $70,000–$100,000 annually at 40 hours/week)
- Contractors must be able to invoice as independent contractors and are responsible for their own taxes and benefits.
Job Type: Full-time
Application question(s):
- When are you available to start?
- What is your desired compensation?
- Have you ever worked for an entrepreneur or early stage company founder before? If so, please provide more details and what made you successful or not successful in that role?
- Please confirm you have reviewed the entire job description - and understand this role is 50% executive assistant work and will require you to manage a calendar and travel arrangements.
This role is best suited for someone who takes pride in being the person behind the scenes who sees around corners, brings order to complexity, and enables a Principal to operate at their highest level across multiple ventures.
Job Types: Full-time, Fixed term contract
Contract length: 12 months
Pay: $70,000.00-$100,000.00 per year
Application question(s):
- Describe a time you proactively prevented a scheduling, logistics, or prioritization issue for a senior leader before it became a problem.
What did you notice early, and what decision did you make?
- When managing an executive’s calendar, how do you decide whether an in-person meeting is realistic and worth scheduling?
Please walk us through the factors you consider.
- Tell us about a time you were supporting multiple priorities or initiatives at once in a remote role.
How did you decide what to prioritize when everything felt important?
- This role involves access to highly sensitive personal and business information.
How do you approach discretion and confidentiality in practice?
- This role is structured as a full-time annual contract.
Please share:
Your desired hourly rate (CAD)
Any flexibility within that range
Confirmation that you are able to work as an independent contractor
Work Location: Remote
