Executive Assistant to Founders; Onsite

The Opportunity

We’re looking for an Executive Assistant who can bring structure, consistency, and reliable follow-through to two very busy founders. In this role, you’ll make sure priorities stay visible, decisions turn into action, and important commitments don’t stall. You won’t be waiting for instructions; you’ll read the situation, understand what matters, and take initiative to move things forward on your own.

You’ll work in person with the CEO and CPO, providing steady, patient, hands‑on support to keep them focused and organized. When details are vague, you’ll clarify them. When something is stuck, you’ll unblock it. When tasks fall off the radar, you’ll surface them again. Your ability to create order, maintain momentum, and “close loops” will directly influence how effectively our leadership team operates.

If you’re calm under pressure, persistent in your follow‑through, comfortable managing up, and naturally inclined to take ownership, this role offers the chance to have a real impact on how the entire company runs.

At Med Me, we are passionate about empowering pharmacists to provide services beyond just prescribing. Our mission is to build an all‑in‑one cloud‑based platform that enables pharmacists to schedule, document, and manage clinical services h over 4,500 pharmacies using our software, we’ve facilitated more than 25 million patient services, transforming pharmacies into community health hubs across North America.

Calendar & Scheduling

• Manage complex calendars for the CEO and CPO, using strong judgment to prioritize what should happen now, later, or not at all.

• Build schedules that reflect real priorities, not just requests.

• Protect time for deep work, travel buffers, and urgent deliverables.

• Coordinate meetings with internal teams, enterprise partners, investors, and external stakeholders across multiple time zones.

• Continuously reorganize and renegotiate meetings as priorities shift.

Task Management

• Actively track commitments, deadlines, and unfinished work across multiple channels and ensure executives follow through.

• Move work forward independently by breaking unclear or incomplete requests into concrete next steps.

• Drive progress without waiting for direction; escalated only when needed.

• Provide consistent, persistent accountability to leaders who move quickly and may require structured prompts to stay on track.

• Maintain reliable systems so tasks, decisions, and loose ends stay visible and nothing gets dropped.

Communication Support

• Help triage inboxes, flag time‑sensitive items.

• Draft clear, concise communications that reflect executive tone and intent.

• Represent the founders professionally with internal teams and external partners.

• Prepare materials for meetings (agendas, summaries, attachments, context).

• Communicate on behalf of the executives when appropriate, with warmth and professionalism.

Travel & Logistics

• Arrange travel from end to end: flights, hotels, transportation, and itineraries.

• Anticipate needs: documents, travel buffers, time zones, prep materials.

• Build itineraries that anticipate needs, time zones, contingencies, and decision points.

• Complete expense reports accurately and on time.

General Support & Coordination

• Assist with occasional personal tasks: bookings, reservations, deliveries, etc.

• Help organize team offsites, events, and executive meetings.

• Maintain organized digital filing systems, documents, and records.

• Coordinate with virtual assistants or contractors if applicable.

• 2-3+ years experience in an executive or administrative role supporting one or more executives, preferably in a startup or high‑paced environment.

• Someone with excellent judgment – you know what’s important and what can wait.

• Patient and flexible in your working style – you know how to support people who think and work differently.

• Extremely organized with excellent time management skills – you rarely drop the ball.

• High follow‑through – you close loops, chase down answers, ensure things don’t stall, drive things to completion.

• Clear, professional communicator with a strong ability to write emails and follow‑ups.

• Comfortable managing up with leaders who may need…