The role
In this role, you’ll provide high-priority support to the CEO, COO, and CMO, managing calendars, coordinating travel, preparing meeting materials, and following up on action items. You’ll also support three additional executives (CPO, CTO, and CFO) with ad-hoc scheduling and coordination as capacity allows.
Your impact
- Provide direct executive support to our CEO, COO, and CMO— including calendar management, travel planning, agenda preparation, briefing notes, and meeting follow-ups.
- Support scheduling and coordination for the CPO, CTO, and CFO as needed
- Support expense reporting and reimbursements for all six executives.
- Act as a trusted partner to the leadership team—anticipating needs, managing competing priorities, and ensuring smooth day-to-day operations.
- Create and maintain systems, templates, and processes that streamline executive operations and internal coordination.
- Support key planning moments across the leadership team, including executive offsites, quarterly planning, and board preparation.
- Contribute to a strong, connected culture across the executive team by helping establish rituals and rhythms that promote clarity, alignment, and impact.
As an Executive Assistant, you will:
What success looks like
In your first 90 days, you'll build trusted working relationships with each of the six executives you support and begin driving impact through strong coordination, communication, and problem-solving. You’ll take full ownership of calendar and travel management, establish efficient meeting rhythms, and implement systems for tracking follow-ups and priorities. You’ll get up to speed on Maple’s tools, processes, and executive workflows, and begin identifying areas where operations can be more streamlined and effective.
Over the following 12 to 18 months, you’ll be a key partner to the executive team, known for your ability to keep things moving, add clarity in moments of complexity, and make the leadership team more effective. You’ll lead planning and logistics for offsites, quarterly reviews, and team-wide priorities, while also supporting the preparation of board and leadership materials. You’ll proactively implement new tools, templates, or workflows that bring greater consistency, efficiency, and transparency to how our executive team operates.
Who you are
- You have 5+ years of experience supporting senior leaders in dynamic, fast-paced environments — this may include Executive Assistant roles or similar roles in operations, coordination, or client service.
- You have a proven ability to manage complex calendars, coordinate travel, and handle executive logistics with discretion, reliability, and professionalism. You are comfortable acting as a trusted partner to senior leaders and can confidently navigate shifting priorities and competing demands.
- You bring excellent written and verbal communication skills. You can draft professional communications, tailor messages to different audiences, and communicate clearly on behalf of others when needed.
- You’re highly organized and detail-oriented. You excel at bringing structure to ambiguity and are always thinking a few steps ahead to anticipate needs and prevent issues before they arise.
- You have strong digital literacy and are comfortable with tools like Google Workspace, Slack, Zoom, and internal systems. You’re quick to learn new tools and often find ways to use them more efficiently.
- You understand the value of follow-through and are experienced with tasks like preparing agendas, capturing action items, and ensuring next steps don’t fall through the cracks.
- You remain calm and solutions-oriented under pressure, and you bring a thoughtful, proactive energy to your work and relationships.
- You also have a strong interest in AI and already use tools like ChatGPT (or similar) to enhance your work—for example, by drafting communications, summarizing meetings, or organizing your workflow.
Play to your strengths. Finding the right fit goes both ways — so this section is yours to complete. When you join, you’ll add the unique strengths you bring that aren't captured above.
How we'll support you
- Maple for you and your family: Free, 24/7 access to general practitioners, pediatrics, and mental health therapy for you and your family. Care starts on day one.
- Comprehensive health coverage: Medical, dental, and life insurance because your peace of mind—and your loved ones—matter most.
- Health Spending Account: Extra funds to cover the essentials that make a difference, from new glasses to specialized therapy.
- Flex Benefits: An annual budget built for your growth and well-being. Use it for professional development, wellness expenses, or a one-time boost to your retirement savings. You choose what matters most.
- Health Days: Life happens. We provide 10 dedicated days for rest, medical appointments, or caregiving, so you can show up at your best.
- Destination Days: Work from anywhere. Enjoy the flexibility to work internationally in eligible countries for up to 5 days per year.
- Group Retirement Savings Plan: We’re here for the long haul. Invest in your future with our group retirement plan.
The details
- Job type: Existing vacancy, full-time
- Hiring manager: Chief Operating Office (COO)
- Location: Hybrid, 225 Richmond St W #201, Toronto, ON M5V 1W2
- Start date: June 2026
- Pay range: $90,000-$105,000
Offers can vary depending on skills, experience, and readiness to meet Maple’s expectations for this level. We encourage open conversations about pay. If you have questions about how compensation works at Maple, you’re welcome to ask at any point in the interview process.
At Maple, we’re committed to the safety and security of our platform. Please note that any offer of employment is subject to a criminal record check (EPIC) and identity verification. Additional checks, including employment or education verification, may be conducted depending on the requirements of the role.
Use of artificial intelligence
At Maple, we do not currently use Artificial Intelligence (AI) or automated tools to screen, assess, or select candidates. Every application is thoughtfully reviewed by our Talent Acquisition team or hiring managers.
Skills Required
- 5+ years of experience supporting senior leaders in dynamic environments
- Proven ability to manage complex calendars and coordinate travel
- Excellent written and verbal communication skills
- Strong digital literacy with tools like Google Workspace and ChatGPT
- Highly organized and detail-oriented
What We Do
About Maple Maple is a virtual care platform that allows Canadians to see a doctor online within minutes — 24 hours a day, seven days a week. Patients can securely text, audio, or video chat with a Canadian-licensed doctor for diagnosis, treatment, and prescriptions. We also offer a wide variety of specialties such as dermatology, endocrinology, and mental health therapy, which can be booked in under 72 hours. Incorporated in 2015, Maple has been operating in Canada since late 2016. We initially launched in Ontario and now offer services in every province and territory of Canada. About our vision Maple is defined by three words — simple, connected, and human. It should be simple to access healthcare. That’s why we created a platform that’s easy to use for Canadians of all ages, abilities, and technology education levels. Healthcare should be connected. We believe that in the future, the majority of wellness and medical care interactions will occur digitally. Our vision is to have Maple be the primary vehicle for healthcare providers to deliver patient care. Maple is on its way to becoming an open-source system to facilitate wellness and care encounters. Maple boasts a streamlined user experience, integrated digital health record keeping, and tools for continuity of care within Canada’s broader healthcare system. The human aspect of medicine should never be forgotten. Our healthcare providers are passionate about what they do, and are dedicated to improving patients’ lives with each virtual care visit. About our team We’re a tightly-knit group of people who are committed to improving the lives of others. We have an ambitious vision, and we’re excited for our team to continue growing.
