Director, Program Management

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:

You’ll be responsible for owning the end-to-end execution of strategic projects across the organization, managing multiple, simultaneous projects that span departments and functions, This includes coordinating cross-functional teams, tracking progress across parallel workstreams, identifying risks early, and proactively removing blockers to ensure timely and successful delivery. The role demands strong organizational agility and the ability to drive alignment across diverse stakeholders while juggling competing priorities.

You’ll work closely with CXOs and leaders across Product, Engineering, and Marketing, the most frequent collaborators, to manage multiple high-impact programs across the company. You’ll also engage with Operations and Finance teams as needed to ensure alignment, accountability, and effective execution at every stage.

This is a hands-on, execution-focused role where your ability to drive results, influence stakeholders, and keep initiatives moving forward will directly impact the organization’s success.

Job Duties

Project Execution \& Delivery

Lead high-priority projects and initiatives from concept to completion, ensuring alignment with executive objectives.

Assess risks, resources, and work requirements, and develop actionable plans for successful delivery.

Manage and drive multiple concurrent projects across different functions, balancing priorities and ensuring the consistent delivery of results.

Monitor progress, track metrics, and ensure accountability across cross-functional teams.

Stakeholder Engagement \& Communication

Serve as a liaison between executive leadership, senior management, and internal teams to facilitate collaboration and communication.

Build and maintain strong relationships with key stakeholders to ensure timely project updates, issue resolution, and alignment.

Develop analyses, presentations, and meeting materials to support executive decision-making.

Engage with stakeholders across multiple geographies and time zones, ensuring seamless coordination globally.

Operational Excellence \& Support

Identify operational gaps and support initiatives that improve efficiency and responsiveness across departments.

Assist with preparation and dissemination of communications related to initiatives and project progress.

Provide data-driven insights and recommendations to support executive decisions.

Qualifications \& Experience

MBA or equivalent experience preferred.

5+ years in project, program, or operational management roles; experience in start-up or high-growth environments is a plus. Working in an e-commerce consumer business or online healthcare consumer business is preferred.

Proven track record of delivering complex initiatives across multiple stakeholders and departments.

Exceptional communication and collaboration skills, with the ability to influence senior leaders and drive accountability.

Strong analytical and problem-solving skills; able to leverage data to inform decisions.

Deeply organized, structured, and calm under pressure; able to move seamlessly between detail and strategy.

Highly organized, proactive, and adaptable in fast-changing environments.

Preferred Skills:

Background in management consulting, operations management, or large-scale program delivery.

Working with engineering and consumer product teams

Strong project reporting and cross-functional coordination skills.

Demonstrated ability to deliver results in a deadline-driven environment.

Demonstrated ability to influence senior leaders without formal authority.

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. "