Join the Digital Health Revolution!
About Pillway
Pillway is Canada’s premier digital pharmacy, redefining patient care through technology, innovation, and relentless operational excellence. We simplify medication management with intelligent adherence tools, personalized care, and seamless nationwide delivery empowering patients and caregivers with a modern, connected healthcare experience.
We aren't just a pharmacy, we are a fast-scaling healthcare technology company driving the future of the industry. By
revolutionizing patient care through proprietary digital solutions, we deliver an unmatched, patient-first model. Join our high-impact team to directly shape the
future of Canadian pharmacy services!
Role Overview
Pillway is seeking an experienced data-driven and strategic Growth Hacker. This role is critical for analyzing post-sign-up behavior, identifying funnel leakages, and implementing re-engagement strategies to increase conversions and customer loyalty on our platform.
Pillway is seeking an experienced Director of Finance that will lead Pillway’s finance, accounting, FP&A, and data analytics functions, serving as a key financial and analytical partner to executive leadership. In this role, you will oversee the finance and accounting team to ensure the accuracy, timeliness, and integrity of all organizational financial information while building scalable processes, reporting capabilities, and robust internal controls.
Core Responsibilities
Champion Financial & Accounting Operations
- Drive core accounting functions including AP, AR, general ledger, and close cycles ensuring pristine financial accuracy and integrity.
- Maintain impeccable financial records across multiple corporate entities and lead consolidated reporting with rigor.
- Optimize liquidity, capital allocation, and internal controls to protect and scale the company's financial health.
- Spearhead process automation and operational enhancements to build a modern, high-efficiency finance department.
Elevate Financial Reporting & Audit Governance
- Deliver seamless monthly, quarterly, and annual reporting packages for executive leadership, board members, and investors.
- Serve as the primary liaison for external auditors and tax advisors, fostering complete audit-readiness and compliance.
Shape Strategic FP&A & Growth Planning
- Lead annual budgeting, continuous rolling forecasts, and dynamic financial models that guide strategic direction.
- Analyze performance trends, cost structures, and variances to unlock actionable insights and maximize profitability.
- Evaluate new investments, key commercial agreements, and expansion opportunities to accelerate business growth.
Lead Data & Analytics Innovation
- Direct the Data & Analytics team to build robust, company-wide business intelligence tools and interactive KPI dashboards.
- Empower cross-functional leaders with data transparency and metrics that inform key operational choices.
Inspire Leadership & Continuous Improvement
- Mentor, develop, and empower a top-tier team across finance, accounting, and analytics.
- Foster cross-functional collaboration across operations, sales, marketing, and customer service to drive organizational excellence.
Required Qualifications
- CPA designation strongly preferred.
- 7–10+ years of progressive finance and accounting experience, including people leadership.
- Strong technical accounting foundation, including financial statements, reconciliations, and audit preparation.
- Demonstrated experience managing accounting teams and overseeing financial operations.
- Strong FP&A capabilities, including budgeting, forecasting, and financial modeling.
- Strong working knowledge of Canadian accounting standards (ASPE or IFRS), including financial statement preparation, consolidated reporting, and external audit requirements
- Advanced Excel skills and experience with financial/accounting systems.
- Ability to interpret business data and communicate financial insights to senior leadership.
- Experience in multi-entity or multi-location organizations preferred.
- Experience with Power BI, Tableau, or similar business intelligence tools is considered an asset.
- Healthcare, pharmacy, technology, or transaction-intensive business experience considered an asset.
Why Join the Pillway Team?
At Pillway, we are transforming pharmacy care across Canada through technology, innovation, and an unwavering commitment to patient-centric healthcare. As our Director of Finance, you will play a pivotal role in shaping our strategic trajectory, driving operational excellence, and scaling a high-impact financial organization.
- Strategic Financial Leadership: Directly influence executive decision-making, capital allocation, and long-term expansion in a high-growth health-tech environment.
- Competitive Compensation & Equity: Receive a highly market-competitive salary, comprehensive health coverage, and opportunities for long-term equity participation through our Employee Stock Option Plan.
- Flexible Work Environment: Enjoy a workplace culture that values flexibility, collaboration, and maintaining strong engagement across corporate teams.
- Innovation & Ownership: Build and scale modern finance, FP&A, and analytics operations, supported by an inclusive, mission-driven team committed to excellence.
Join us at Pillway for a chance to shape the future of digital healthcare, where your work impacts lives daily, and innovation meets inclusivity.
Our Commitment to You
Pillway supports a workforce of diverse backgrounds and encompasses policies and initiatives designed to help all employees feel welcomed and well-equipped to succeed. We are an inclusive employer and provide accommodations for applicants with disabilities throughout the recruitment process. Please let us know if you require accommodation.
Note: We appreciate every application we receive, but due to our overwhelming response, we will only be able to contact those who are under consideration for the position.
Disclosure: We use AI tools to assist with screening and evaluating application
