Founded in 2015, Maple is a fast-growing health tech company with a vision to power the future of healthcare by building a connected and superior experience for patients, doctors, and other types of health providers.

We offer virtual care services across multiple distribution channels, including Direct-to-Consumer ("B2C"), Employers and Private Insurers ("B2B") and Public Sector Institutions ("B2I"). With a growing network of 2,000+ healthcare providers and nearly 4 million Canadians with access to our services, Maple is one of Canada’s fastest-growing virtual care companies.

We have established an entrepreneurial culture centered around our purpose to support people’s health and well-being and to strengthen the healthcare system. We attribute our success to our team, who has helped us achieve numerous noteworthy awards including: LinkedIn's Top 10 Startups, Deloitte Canada’s Technology Fast 50, Globe & Mail's Top Growing Companies in Canada, North America’s Inspiring Workplaces, and Glory Professional’s The Power 50: Canada’s Most Impactful Companies.

THE POSITION

We’re looking for a highly organized, tech-forward, and proactive Executive Assistant (EA) to support our executive team. 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.

This is a high-impact, high-trust role with visibility across the business. Clear communication will be key — we’ll rely on you to flag when capacity is limited or priorities need to shift, so we can stay aligned and support you in focusing on what matters most.

You’ll be a great fit for this role if you have past experience as an Assistant, as well as in roles like project coordination, client-facing work, operations, communications, or office management — working in fast-paced, high-accountability environments. You’re a quick learner, highly organized, tech-savvy, an excellent communicator, and energized by helping others operate at their best.

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.

12-18 MONTH DELIVERABLES

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.

KEY COMPETENCIES

Organizational Skills
Time Management
Detail Orientation
Communication
Digital Literacy

CANDIDATE PROFILE

You have 5+ 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, such as drafting communications, summarizing meetings, or organizing your workflow.

Not checking every box? Please apply anyway. We understand that candidates have different experiences that may make them a fantastic fit for this position, and for Maple. We value equity, diversity, and inclusion, and we’re committed to providing fair and equal opportunities to all applicants. We also want to provide an accessible interview process, so if there’s any accommodations that would make your experience more comfortable, please let us know.

OUR CORE VALUES

We are a team: We’re team Maple. We’re better together. We support each other, face challenges collectively, and are united in a belief that we can make a positive difference in healthcare, as one.
We can do big things: We’re bold. We know that if we push the boundaries, and inspire each other to dream bigger and think differently, we will realize our incredibly ambitious goals.
We celebrate wins and own mistakes: We empower each other to own our contributions. We celebrate and learn from our achievements, and we recognize and learn from our mistakes.
We get better every day: We never settle. We’re always learning and improving, always seeking feedback, and we tackle challenges with a belief that better is always possible—in ourselves, our processes, our products and our services.
We’re all the way in: We’re fully committed. We strive for excellence, are driven by our purpose, and we act with urgency to fulfill it every day.

WORKING AT MAPLE

We want you to love working at Maple—feeling challenged, supported, and cared for. Just as we strive to grow and improve, we encourage you to embrace the same mindset as you work toward your personal best. Together, we can learn, develop, and power the future of healthcare. At Maple, your success is our success.

We care about your health and well-being. Here’s how we’ve got you covered:
Competitive benefits package: health, dental, counselling, and life insurance coverage to care for you and your loved ones.
Health spending account: extra funds for wellness essentials like eyeglasses, therapy, and more.
Wellness budget: recharge with activities that fuel your well-being—fitness classes, mindfulness tools, and beyond.
Maple access: virtual healthcare for you and your family, including general practitioners, pediatrics, and therapy consultations.
Paid health Days: 10 extra days for when life happens—rest, appointments, or caregiving included.
Destination5: work internationally in eligible countries for up to 5 days per year.
Retirement savings plan: invest in your future with our group retirement savings plan.
Branch out budget: $1,000 annually to pursue professional development and fuel your growth.

OTHER

Job type: Full-time
Hiring manager: Chief Operating Officer (COO)
Location: Hybrid, 225 Richmond St W #201, Toronto, ON M5V 1W2, 3-4 days in office weekly
Start date: August 2025
Vacation: 3 weeks

Please note that any offer of employment may be subject to verification of employment and education background checks, including a criminal record check.

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