Executive Assistant

Maple; Toronto; Hybrid; CAD 60,000 - 100,000; Full time

Job summary

An innovative health tech company is seeking a proactive Executive Assistant to support its leadership team. This role offers the chance to work closely with senior executives, managing their calendars and travel while ensuring smooth day-to-day operations. With a focus on organization and communication, you'll help shape executive support as the company scales. Join a dynamic environment where your contributions will directly impact the future of healthcare and enhance the experience for patients and providers alike. If you're detail-oriented and thrive in fast-paced settings, this opportunity is perfect for you.

Benefits

Health and dental insurance

Health spending account

Wellness budget

Virtual healthcare access

Paid health days

International work opportunities

Retirement savings plan

Professional development budget

3 weeks vacation

Qualifications

• Experience in managing complex calendars and competing priorities.
• Proven ability to support senior leaders beyond scheduling.

Responsibilities

• Provide specialized executive support to CEO, COO, and CMO.
• Manage calendars, travel, and prepare meeting agendas.

Skills

Organizational Skills

Time Management

Detail Orientation

Communication

Digital Literacy

AI Literacy

Education

5+ years as an Executive Assistant

Tools

Google Workspace

Slack

Zoom

Job description

ABOUT MAPLE

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, proactive, and detail-oriented Executive Assistant (EA) to support our executive team.

In this role, you’ll provide specialized and priority EA support to our CEO, COO, and CMO—including calendar and travel management, meeting preparation, agenda development, and handling follow-ups.

For the remaining three executives — the CPO, CTO, and CFO — you’ll provide ad-hoc calendar support as capacity allows, primarily around scheduling and coordination. This is a high-trust, high-impact role with visibility across the business, and an opportunity to help shape how executive support operates at Maple as we scale. 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.

YOUR IMPACT

• Provide specialized executive support to our CEO, COO, and CMO—including managing calendars, planning travel, preparing agendas, briefing documents, and capturing action items.
• Deliver ad-hoc calendar support and coordination to three additional executives.
• 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 will establish trusted relationships with each of the six executives you support and quickly take ownership of their calendar and travel coordination needs. You’ll ramp up on high-touch EA support for the CEO, COO, and CMO, including weekly meeting preparation, agenda development, and handling post-meeting follow-ups. You’ll also familiarize yourself with internal systems and tools, identify opportunities for more efficient workflows, and begin managing executive expenses.

Over the next 12 to 18 months, you’ll become a trusted and indispensable partner to Maple’s executive team—known for your reliability, discretion, and ability to keep things moving. You’ll lead planning and logistics for executive team meetings and offsites, support the preparation of board and leadership materials, and introduce new systems or templates that bring consistency and efficiency to executive operations.

KEY COMPETENCIES

• Organizational Skills
• Time Management
• Detail Orientation
• Communication
• Digital Literacy

CANDIDATE PROFILE

• 5+ years of experience as an Executive Assistant, supporting multiple senior leaders in high-growth or fast-paced environments.
• A proven ability to manage complex calendars and competing priorities with discretion and efficiency.
• Experience coordinating domestic and international travel, handling expenses, and managing executive logistics end-to-end.
• Highly organized and detail-oriented, with a skill for bringing structure to ambiguity.
• Proven ability to support senior leaders beyond scheduling—e.g., preparing for meetings, drafting agendas, capturing action items, and ensuring follow-through.
• Exceptional written and verbal communication skills—you can write clearly, professionally, and in the voice of those you support.
• Tech-forward mindset and capabilities —you’re fluent in Google Workspace, Slack, Zoom, and can quickly learn new tools and systems.
• Strong AI literacy—you already use AI tools like ChatGPT or others in your day-to-day work (e.g., for drafting content, summarizing meetings, organizing tasks) and are excited to explore new ways to integrate AI into your workflows.
• Calm, proactive, and solutions-oriented—you bring clarity and trust to every interaction, even in fast-moving or high-pressure situations

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: June 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.