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Role: Executive Assistant to CEO (Canadian group travel company)

Priority Location: Any

Working Hours: 40 hours per week, flexible schedule based on the client’s extensive travelling

Salary Range: $1,500 - $2,000 USD ($) per month

(The final offer is at the client’s discretion and depends on the candidate’s interview result, skills, and experience.)

Type of contract: Independent Contractor

Type of job: Remote

Role Profile:

The CEO’s Executive Assistant provides day-to-day executive support to the CEO of the company and serves as the central point for managing his communications, tasks, priorities, scheduling, approvals, and administrative needs.

The mandate is simple to state and demanding to execute: take ownership of the administrative and operational layer of the CEO's work so that he can concentrate on strategy, hosting, content, and growth.

This role requires someone with prior successful Executive Assistant experience who can quickly learn the CEO's working style and the company's processes. The right person will initially ask questions and seek precedent rather than make assumptions, and will progressively recognise patterns, anticipate needs, and operate independently as their knowledge of the role develops.

Scope of Responsibilities:

Executive Office

Manage the CEO’s day-to-day workload by organizing incoming requests, determining priorities and ownership, coordinating schedules, and ensuring tasks move through completion.

This includes:

CEO Email Management: full ownership of the CEO's primary inbox: reading, categorising and triaging all incoming mail daily; responding directly to routine correspondence in the CEO's voice; routing items to the appropriate team member and confirming follow-through; and surfacing what genuinely requires the CEO's attention with clear framing and a recommended next step. A separate private inbox for sensitive matters sits outside this role.
CEO Task & Project Management: maintaining the master view of active projects, owners, deadlines and next steps; running follow-ups so that nothing waiting on a third party is lost; and providing a regular briefing that identifies the few items requiring the CEO's focus and what is blocked and on whom.
CEO Calendar & Scheduling: ownership of the CEO's calendar, including complex multi-time-zone scheduling, protection of focused work blocks, and accepting, declining, proposing and rescheduling meetings on his behalf in routine cases.
Travel Logistics: support with flights, hotels, ground transport, complex routings and expense capture.
CEO Non-W&A Personal Projects: administrative support for the CEO's projects outside the business.

Executive Communications & Approvals

Coordinate communications requiring CEO input or approval by collecting information and drafts from the appropriate teams, reviewing them for completeness and quality, presenting them to the CEO, communicating feedback, and tracking them through to completion. Draft correspondence in the CEO's voice, which is documented and carries specific conventions on tone, length and language.

Executive Coordination

Coordinate activities involving the CEO by liaising with internal teams, scheduling meetings and events, gathering required information, and ensuring preparations are complete before the CEO’s involvement.

Executive Administration

Handle administrative responsibilities that directly support the CEO and maintain the documentation required for the role.

This includes:

Invoice Collection — collecting invoices and charges and liaising with the bookkeeper, including clarification of expenses with the team and ensuring regular financial reporting reaches the CEO on schedule. This is a coordination role; the books themselves remain closed to it.
Documentation / SOPs — maintaining existing documentation and documenting new processes once workflows are understood.

Candidate Profile:

Experience & Seniority

Experienced Executive Assistant: Must have previously supported a senior executive or CEO successfully and understand the expectations and pace of executive-level support.
Independent but Coachable: Experienced enough to take ownership and exercise judgment, while remaining open to learning established processes and adapting to the CEO’s preferred way of working.
Fast Learner: Able to absorb new information, processes, tools, and context quickly and translate what they learn into independent execution.
Progressive Autonomy: Seeks clarification and precedent when something is unfamiliar, but learns from previous situations and requires progressively less direction over time.
Remote-native: Demonstrated success working fully remotely, self-managing and self-motivated, without daily supervision.
Small-business fluency: Comfortable in an environment where roles flex and process is built as you go. Travel industry experience is welcome but not required.

Soft Skills

Discretion & Confidentiality: Handles sensitive information with complete reliability.
- Looks like: Treats legal, financial, personnel, and member-relationship matters as closed by default; never discusses one party's business with another.
- Does not look like: Sharing context "helpfully" with colleagues who did not need it.
Judgment Under Ambiguity: Knows which decisions to make alone and which to bring to the CEO.
- Looks like: Reads a request, an email, or a team dynamic and makes a sensible call; escalates the genuinely consequential and handles the rest.
- Does not look like: Escalating everything to be safe, or deciding on matters that carry real risk without checking.
Critical Thinking & Sound Judgment: Gathers the necessary information and makes well-reasoned decisions without jumping to assumptions.
Proactivity & Follow-Through: Takes ownership, anticipates next steps, and follows work through to completion.
- Looks like: Chases the third party before the deadline rather than after it; provides crisp status updates without being asked; nothing drifts.
- Does not look like: Waiting to be asked, or reporting that something is "still pending" without having pursued it.
Organization & Prioritization: Brings order out of a high volume of competing demands.
- Looks like: Can produce an accurate view of every live commitment on request, without preparation time.
- Does not look like: An accurate list that requires an hour to assemble.
Learning Agility & Pattern Recognition: Learns from instruction and precedent, then applies it independently.
- Looks like: Handles the third instance of a recurring situation without asking how the first two were handled.
- Does not look like: Asking the same question each time it recurs.
Clear & Concise Communication: Communicates efficiently and reduces noise rather than adding to it. Excellent written and verbal English communication skills.
- Looks like: Presents ranked options with a recommendation rather than open-ended questions; a briefing the CEO can act on as written.
- Does not look like: Forwarding a long thread with "thoughts?" attached.
Working From Partial Information: The CEO works in a fast, high-context, asynchronous style, often through voice memos, transcripts, and fragments.
- Looks like: Takes a two-minute voice note and returns a finished draft, a scheduled meeting, and three delegated items.
- Does not look like: Requesting a fully formed brief before starting.
Professional Steadiness & Boundary-Holding: Holds the line on the CEO's behalf without creating friction.
- Looks like: Declines a request from a senior colleague pleasantly and firmly, and protects the CEO's focused time.
- Does not look like: Absorbing whatever work arrives from whoever asks most persistently.
Adaptability & Problem-Solving: Adjusts quickly to changing priorities and finds practical ways to move work forward.
Tech & AI Agility: Adopts new technology and AI tools quickly and uses them to improve output.
- Looks like: Uses AI fluently to produce strong first drafts, then refines them with judgment.
- Does not look like: Sending unedited AI output or avoiding the tools altogether.

Technical Skills

Google Workspace: Advanced proficiency in Gmail, Calendar, Docs, Drive, and Google Sheets. Uses Google Sheets confidently to organize, track, and maintain information.
Slack: Proficient in using Slack for communication, coordination, and task follow-up.
AI Tools: Proficient in using AI for research, drafting, summarizing, organizing information, and improving work efficiency. Practical working experience with Claude, ChatGPT or comparable tools. This is not optional.
Business Writing: Strong professional writing, editing, proofreading, and document-review skills.
Task Management Systems: Comfortable working with digital task and workflow management systems; Monday.com or HubSpot experience is an asset.
Digital Organization: Able to maintain organized files, documentation, trackers, and information across multiple systems.
Monday.com / HubSpot: Experience is an asset (not mandatory)

Reporting & Working Model:

Reports to: The Founder & CEO, exclusively. The Executive Assistant coordinates with the operations, sales, marketing, and finance teams as required, but does not take direction from them and is not a shared administrative resource for the wider team.
Location: Fully remote. There is no in-person requirement.
Engagement: Full-time independent contractor from the outset.
Hours: The CEO travels extensively and works out of many different time zones (Usually he is working from North America, Europe, or Southeast Asia). The role calls for someone who manages their own schedule and can adjust start and end times to ensure an overlap with the CEO's hours, regardless of the time zone he is in.
Structured review period: The first 90 days operate as a structured review period with reviews at 30, 60, and 90 days.

Executive Assistant to CEO 64519540287