Director, Commercial Operations
Maple
Operations
Toronto, ON, Canada
Posted on Nov 8, 2025
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, nurse practitioners 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 7 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 have 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 hiring for a Director, Commercial Operations to build and scale the operational foundation that powers Maple’s B2B and B2I commercial engine. This is a strategic and hands-on leadership role responsible for integrating Sales Operations, Client Success Operations, and Commercial Enablement into a cohesive, data-driven function.
You’ll join at an exciting time as we continue to expand our enterprise partnerships, modernize our product suite, and evolve the systems and processes that drive predictable growth. Your work will directly impact Maple’s ability to deliver a seamless partner experience, improve forecasting accuracy, and unlock efficiency across the entire commercial lifecycle — from acquisition to retention and growth.
This is a unique opportunity for a commercially minded operator who thrives at the intersection of data, strategy, and execution.
YOUR IMPACT
- Build and lead Maple’s Commercial Operations function, integrating sales operations, client success operations, and enablement under a unified strategy.
- Partner closely with cross-functional leaders to shape Maple’s go-to-market execution, enabling scalable growth across multiple distribution channels.
- Lead the optimization of forecasting, commission, and performance frameworks that drive accountability and insight.
- Strengthen the connection between data and decision-making — from pipeline visibility to renewal analytics — empowering leadership with actionable intelligence.
- Oversee Salesforce and the broader commercial tech stack, ensuring systems support strategic outcomes, not just transactions.
- Collaborate with Finance, Product Marketing, and Clinical Operations to drive alignment, simplify workflows, and enhance visibility across teams.
- Lead and mentor a small, high-performing team that blends analytical strength with operational creativity.
WHAT SUCCESS LOOKS LIKE
In your first 90 days, you’ll dive deep into Maple’s commercial ecosystem — meeting key leaders, understanding how our revenue engine runs today, and identifying opportunities for immediate impact. You’ll begin to streamline reporting, align forecasting inputs, and build trust as a collaborative thought partner to the Sales and Client Success teams.
Over the next 12 to 18 months, you’ll design and execute a Commercial Operations roadmap that transforms how Maple plans, measures, and delivers results. You’ll bring greater predictability to forecasting, elevate our commercial data strategy, and launch scalable processes that unlock time and focus for our external-facing teams. Ultimately, your success will be measured not just in operational improvements, but in the growth, clarity, and confidence you enable across the business.
CANDIDATE PROFILE
- 8+ years of progressive experience in Commercial, Sales, or Revenue Operations, ideally spanning both pre- and post-sales functions.
- Proven success building or scaling operations in a B2B or channel-driven organization; SaaS, benefits, or health tech experience a plus.
- Deep understanding of go-to-market dynamics — you think beyond sales metrics to how systems, incentives, and data flow across the entire customer lifecycle.
- Strong analytical and systems expertise; fluent in Salesforce and comfortable shaping how insights inform decisions.
- Strategic thinker who can zoom out to design frameworks and zoom in to execute when needed.
- Demonstrated success partnering with cross-functional leaders (Sales, Client Success, Marketing, Finance, Product) to align on goals and deliver measurable results.
- Confident communicator and trusted advisor to leadership; skilled at translating operational complexity into clear business stories.
- Thrives in ambiguity, builds trust quickly, and balances precision with pragmatism.
- Resilient, curious, and energized by making things better every day.
- 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: Amii Stephenson
- Location: Hybrid, 225 Richmond Street West, Toronto, ON
- Start date: Jan/Feb 2026
- Vacation: 4 weeks
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 are any accommodations that would make your experience more comfortable, please let us know.
OUR CORE VALUES
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:
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Please note that any offer of employment may be subject to verification of employment and education background checks, including a criminal record check.
