Flagship Solutions jobs

CLOUD GROUP OF COMPANIES

Executive Assistant / Personal Assistant

to the President — Cloud Group of Companies

LOCATION

Vancouver, BC · on-site

EMPLOYMENT

Full-time

COMPENSATION

$90,000 – $110,000

TRAVEL

Moderate to high

About the Cloud Group of Companies

Cloud Group of Companies is a growing collection of healthcare, technology and investment businesses — including Cloud Pharmacy (with locations across Canada), Cloud eHealth Technologies and Mandelbrot Imaging Technologies. Canada Cloud Pharmacy, our flagship, is a trusted online pharmacy delivering affordable, accessible healthcare to customers across Canada. Together, the group operates at the intersection of pharmacy, digital health, imaging AI and holdings.

The role

We are hiring a highly organized, proactive and discreet Executive Assistant / Personal Assistant to serve as the President's dedicated, professional right hand. Unlike a shared or departmental EA, this role is entirely focused on the President — protecting their time, running their day, and enabling clear, well-informed decisions across every entity in the group.

The role combines executive support, personal assistance, operational coordination and light project management across business and personal priorities. You will be a trusted partner who anticipates needs, handles highly confidential information with total discretion, and consistently delivers to a high bar of detail and follow-through.

How you'll work — what makes this role different

These are the operating standards that define success in the role and separate a great candidate from a good one:

• Single point of executive control. Meeting requests, scheduling and inbox triage for the President route through you. You defend the calendar, ask the right intake questions (purpose, duration, agenda, attendees) before booking, and place every commitment in the right time-block — never across protected Deep Work time.
• Total discretion and a one-way confidentiality firewall. You gather context inward from other assistants, staff and systems to inform the President — but nothing about the President's matters flows back out. Confidentiality is a defining feature of the role.
• No decision without context. The President is highly detailed. Every issue you bring forward carries background, options, cost/risk, and your recommendation — never a half-formed ask. Anticipate follow-up questions and answer them in advance.
• Instructions followed exactly. When the President gives you an instruction, execute it as given. If something seems off, ask before deviating — never improvise around a clear instruction.
• Close the loop, every time. Nothing is left open or assumed done. Confirm completion, file the outcome in its one official home, and surface it where the President will see it.
• Multi-entity awareness. You'll coordinate across the Cloud Pharmacy network (BC, Toronto, Winnipeg), technology and health businesses (Cloud eHealth, Mandelbrot Imaging, ML Health, Lumen Dental AI), and the President's holdings and ventures.

Executive support

• Own the President's calendar end-to-end: meetings, appointments, deadlines and priorities.
• Review and triage all inboxes daily; surface what needs the President's attention; respond to what you can in the President's voice.
• Run meeting intake for every incoming request — purpose, duration, agenda, attendees — and book by priority and availability.
• Prepare and package decisions using the President's standard brief format (background, options, cost/risk, recommendation).
• Attend meetings, capture minutes and action items, and drive follow-through to closure.
• Coordinate complex domestic and international travel, accommodations, transportation and detailed itineraries.
• Support cross-entity initiatives, project tracking and coordination with department leads, external stakeholders, vendors and partners.
• Maintain filing, documentation, workflows and trackers per the Cloud Group's Golden & Silver Rules (one-home filing, hierarchical naming, reference numbers).
• Prepare reports, presentations, meeting materials and executive communications to a high standard of polish.
• Operate fluently across Microsoft 365 (Outlook, Teams, SharePoint, Planner, To Do, Loop, Word, Excel, PowerPoint) and AI tools (Microsoft Copilot, ChatGPT, Claude, Perplexity) to work faster and better.

Personal assistant support

• Manage personal appointments, reservations and day-to-day commitments.
• Coordinate household vendors, contractors, maintenance, deliveries and service providers.
• Handle personal errands and requests: purchases, groceries, meals, pickups, returns, deliveries.
• Keep the home environment organized — spaces, supplies, logistics — running smoothly and discreetly.
• Plan and coordinate personal projects, home initiatives, events, celebrations and special requests.
• Support personal travel: planning, transportation, reservations and lifestyle logistics.
• Maintain personal records, schedules, reminders and ongoing commitments.
• Research products, vendors, services and solutions across both business and personal needs.
• Anticipate what's coming and proactively resolve issues before they reach the President.

What we're looking for

Experience

• 10+ years supporting senior executives, founders, entrepreneurs or business owners as an Executive Assistant, Personal Assistant, Chief of Staff or in a similar role.
• Proven track record supporting a C-suite principal directly — not through a shared pool.
• Demonstrated confidentiality: comfortable handling legal, financial, HR, health and other highly sensitive information.
• Experience coordinating complex travel and scheduling, including cross-border and multi-time-zone arrangements.

Skills and tools

• Advanced Microsoft 365: Outlook, Teams, SharePoint, Planner, To Do, Loop, Word, Excel, PowerPoint.
• Working fluency with AI tools (Copilot, ChatGPT, Claude, Perplexity) and a willingness to keep learning.
• Exceptional written and verbal communication — clear, concise, professional; comfortable drafting on the President's behalf.
• Excellent organizational and prioritization skills; you file, name and track things consistently so nothing is lost.
• Strong problem-solving and independent judgment; you bring solutions with your problems.

Attributes

• Detail-oriented and precise — "roughly" and "I think" are red flags; you verify, then report.
• Proactive; you anticipate needs before they arise.
• Discreet, mature and unflappable under pressure.
• Adaptable and resourceful; comfortable with responsibilities that vary from day to day.
• High-trust, high-accountability operator who takes ownership and closes loops.

Practical requirements

• Valid driver's licence and comfortable driving.
• Able and willing to travel domestically and internationally as required.
• Comfortable working across office, residence, travel and event environments.
• Available for trusted-partner responsiveness outside standard hours when the business or personal calendar genuinely requires it (evenings, weekends, urgent matters). This is not a 24/7 always-on role — it is a role where the President can rely on you when it matters.

Your team

You will join a group of executive assistants who work under the President and Director of the companies. Your role is designed to be the professional, ring-fenced EA — fully dedicated to the President — while working cooperatively alongside the existing assistants. You'll gather context from them and hold the confidentiality line consistently in the other direction.

Why this role

• Direct partnership with the President — no shared pool, no departmental split, no politics.
• Multi-entity exposure across pharmacy, digital health and imaging AI — a genuinely broad remit.
• Sophisticated tooling and standards — you'll work inside a well-defined operating system (Golden & Silver Rules, time blocks, decision briefs), not in chaos.
• A high-trust environment where discretion and judgment are recognized and rewarded.
• Real career growth potential as the group expands.

How to apply

Please apply directly with:

• A current résumé.
• A short cover note (200–300 words) explaining why this role fits you and describing an example of a time you managed a sensitive, high-stakes situation for an executive.
• Two professional references (we will not contact them without your permission).

Applications will be reviewed on a rolling basis. Only shortlisted candidates will be contacted for interview.

Cloud Group of Companies is an equal-opportunity employer. We welcome applications from candidates of all backgrounds.

Pay: $90,000.00-$110,000.00 per year

Work Location: In person