Executive Assistant

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.

• 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.

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

• 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

• 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.

• 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.

• 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