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 at scale. You’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 cash flow management and financial risk mitigation across a complex, multi-provincial operation
• Roll up your sleeves during critical periods—this is a hands-on leadership role, especially during transition and rapid scaling phases

Develop a World-Class Finance Organization

• Mentor an exceptional finance team that matches the calibre of our mission
• Instill a culture of financial discipline, radical transparency, and strategic thinking
• Partner seamlessly with operations, product, clinical, and business development leaders to drive integrated decision-making

Qualifications & Experience

• 4-5 years as CFO at a venture-backed or high-growth consumer technology company where you were instrumental in driving results
• You've lived the 4-5x growth story as a CFO or VP Finance and know exactly what it takes to scale financial operations during hypergrowth
• You've successfully led multiple fundraising rounds (Series B through pre-IPO and beyond) and built lasting relationships with institutional investors
• You've navigated complex capital structures and managed diverse stakeholder interests with sophistication
• You're hands-on when it matters—willing to dive into the details during critical moments while never losing sight of strategy
• You thrive in high-intensity environments and bring the stamina to lean in during critical growth periods, matching the pace and commitment of a leadership team that consistently goes the extra mile.

Strategic Vision

• You possess deep expertise in consumer SaaS/subscription business models and understand unit economics at an intuitive level
• You have sophisticated knowledge of capital markets, investor relations, and corporate finance principles
• Your financial modelling, forecasting, and analytical capabilities are world-class
• You can translate complex financial concepts into compelling narratives for any audience

Leadership That Inspires and Delivers

• You communicate with exceptional clarity and persuasiveness to boards, investors, team members, and cross-functional partners
• You think strategically while executing with relentless discipline
• You've proven you can operate effectively in fast-paced, resource-constrained startup environments
• You command executive presence and credibility with institutional investors and board members
• You're as comfortable challenging assumptions as you are building consensus

What We Offer

This isn't just another finance role—it's a defining career opportunity:

• Mission-Driven Impact: Shape the financial strategy behind a platform that's genuinely transforming healthcare access for millions of Canadians
• Significant Equity Upside: Meaningful ownership in a company attacking a $45B market opportunity
• Exceptional Leadership Team: Work alongside mission-driven founders and operators who are building something extraordinary
• Hybrid Flexibility: 3-4 days per week in our Vancouver/Surrey office, balancing collaboration with focus time

Benefits

Join our team and enjoy a benefits package designed to support your health and well-being, including dental and vision care, as well as extended health care coverage. We provide disability insurance for added security and life insurance to protect your loved ones. To promote work-life balance, you’ll receive paid time off, including vacation days. Additionally, we offer a Group Retirement Savings Plan (GRSP). Experience a workplace that truly cares about you!

The annual compensation is based on a number of factors and may vary depending on job-related knowledge, skills, experience and alignment to the market .

" Pocketpills is committed to creating an accessible and inclusive organization. We are committed to providing barrier-free and accessible employment practices. Should you require accommodation through any stage of the recruitment process, please make them known when contacted and we will work with you to meet your needs. "

Reports to: CEO

Company: Pocketpills.com

Total Addressable Market: $45B