Executive Assistant to the Founders (Onsite)

What You’ll Do

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; escalate 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

About You

• 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 structure, prompts, and persistent hands-on support to stay on track
• Tech-savvy and confident navigating Google Workspace, Slack, Notion, and virtual meeting tools
• Comfortable handling confidential information with care and discretion
• Based in Toronto and able to work in person most days; open to occasional travel throughout the year

How We Hire

MedMe is committed to a fair and equitable hiring process for all candidates. Our team personally reviews every application to ensure a human-first approach; we do not use AI tools to assess or select applicants. To ensure that each candidate’s journey is consistent and the selection process is unbiased, the team at MedMe will not be responding to any personal messages regarding this role or other opportunities.

The Interview Process

1. A brief call with a hiring team member to get to know you better and discuss role expectations
2. A short practical case study to showcase your problem-solving and communication skills
3. A 30-minute call with member(s) of the executive team
4. An offer, contingent on mutual alignment

Perks at MedMe

• Professional Development: We support your growth with a yearly budget dedicated to learning opportunities
• Work-from-Home Stipend: A dedicated stipend to help set up and maintain your ideal home office
• Office Closure for Holidays: Enjoy 1-2 weeks of company-wide office closure during the holidays
• Company Retreats: Participate in exciting on-site team retreats for collaboration and bonding

Location

This is a fully in-person position, based at our office located at the intersection of Adelaide and Spadina in Toronto. There may be opportunities to work from home on certain days, depending on in-office attendance and operational needs.

MedMe is a proud equal opportunity workplace that is committed to equal employment opportunity regardless of race, colour, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We’re looking for motivated and compassionate people who can execute from the ground up and support the work that MedMe believes in.

MedMe is committed to developing an inclusive, barrier-free recruitment process and work environment. Should you require any accommodation, please inform us and we will work with you to meet your accessibility needs. For any accessibility-related assistance, requests for information in accessible alternative formats or to report any accessibility problems, please share in your application.

A meeting lands on your calendar

If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.