CFO

Overview  We’re a healthcare platform for humans, designed for real life. Pocketpills is Canada’s leading online pharmacy & medical care platform. Re-imagining healthcare to make it accessible, affordable and built for people like you. Driven by our passion for innovation and customer-care, we’ve designed a suite of digital care experiences that empower our members to take control of their health wherever life takes them.

From coast to coast, over 800,000 Canadians trust Pocketpills to deliver their medication & ensure a healthcare professional is always just an arms-reach away.
We founded Pocketpills as a solution to fix the broken system that made getting care harder than it needed to be. We don’t believe long line ups at the doctor’s office, confusing refill protocols & one-size-fits-all advice, actually fit with what Canadians need, so we’ve changed the game. Powered by pharmacists, engineers, doctors, clinicians & service experts, our platform redefines the world of wellness, from personalized treatment that actually feels personal, to truly effortless refills, including free, friendly delivery.

Because we do believe Canadians deserve a better way to manage their most important asset, their health.
Discover the healthcare platform that feels Delightfully Human. With Pocketpills, complete care is right in your pocket.
About the Role  This is more than a CFO role—it's a once-in-a-career opportunity to solve one of Canada's most pressing healthcare challenges.
We're seeking an exceptional Chief Financial Officer who sees beyond spreadsheets to the transformative impact of solving real problems ’ll be the financial architect behind our mission to drive 3–5x growth in the near term and to build the financial and operational foundations for the decade ahead, enabling us to serve millions more Canadians.
This role demands someone who thrives at the intersection of high-stakes finance and purpose-driven impact. You'll navigate complex capital markets, lead critical equity and debt fundraising efforts, and build financial systems that scale—all while working alongside a leadership team obsessed with revolutionizing Canadian healthcare delivery.
This is a high-impact, high-intensity opportunity where the pace naturally accelerates during key growth moments. You’ll be joining a team of passionate leaders who consistently go the extra mile to make a meaningful difference in the lives of Canadians through innovative healthcare products. As a fellow leader, you are expected to lean in with us during these high-intensity periods—bringing both top-tier financial sophistication and the drive to help build something that genuinely matters.
What You'll Do  Shape the Financial Future of Canadian Healthcare
Architect and execute the comprehensive financial strategy that will fuel our 3-5x growth trajectory in the near term, while laying the foundation for sustainable scale over the decade ahead
Own all financial planning, budgeting, and forecasting as we scale across provinces, diversify therapeutic areas, and build the groundwork for future national and global reach
Serve as a trusted strategic advisor to our CEO and Board on capital allocation, M&A opportunities, and critical business decisions
Drive financial performance across multiple high-growth business units serving diverse patient populations nationwide
Master the Capital Markets Game
Lead high-stakes fundraising efforts with Canadian and international institutional investors
Craft and deliver compelling investor narratives that communicate both our financial strength and societal impact
Navigate sophisticated capital structure decisions involving equity, debt, and hybrid instruments while optimizing for growth and stakeholder value
Build and maintain world-class relationships with current investors and prospective capital partners
Build Financial Infrastructure for Scale
Design and implement robust financial systems, controls, and processes capable of supporting explosive growth
Lead all accounting, financial reporting, treasury, and tax functions with precision and regulatory compliance
Drive quarterly and annual close processes with accuracy and efficiency
Master…