Director, Engineering

When it comes to health, we’re always looking for ways to push for better. It’s why we were founded in the first place. In 1957, our founder, pharmacist William Wilkinson, witnessed a mother sacrifice her health by forgoing her own medicine to pay for her sick daughter’s prescription. He knew there had to be a better way. So, he introduced North America’s first prepaid drug plan, and GreenShield was born as a not-for-profit with a mission to support better health for all Canadians.

We aren’t just a health and benefits company. We’re the only not-for-profit social enterprise that brings worlds of coverage and care together, all in one place.

We’re noble challengers, purposefully building a better way and we need the best people to help us create a more holistic approach that takes care of the mind and body.

Our mission is to create better health for all Canadians, and we know that starts with our employees.

THE ROLE IN A NUTSHELL

We are seeking a Director of Engineering for our software engineering lab. This role is ideal for a visionary leader with a startup mentality and extensive experience in managing software engineering teams. The successful candidate will have a strong background creating modern web and mobile applications, developing Software as a Service (SaaS) and enterprise solutions,

and leveraging Artificial Intelligence (AI) for application development. We are looking for a leader passionate about innovation in healthcare, with over 10 years of senior leadership experience in a technology-driven environment and hands‑on experience as a software engineer.

Responsibilities

• Leadership in Engineering: Direct a world‑class software engineering team, encouraging innovative approaches to problem‑solving and product development.
• AI‑Driven Development: Utilize expertise in AI to innovate and enhance application development processes and products.
• Strategic Technical Roadmaps: Create and implement technical roadmaps that align with the lab’s objectives, focusing on the application of AI technologies.
• Collaboration and Innovation: Work closely with the product and architecture teams, business and other stakeholders, to design and deliver scalable, cutting‑edge software solutions.
• Product Development Excellence: Oversee the development lifecycle, ensuring that products are technically robust and meet market needs.
• Strategic Planning and Execution: Provide strategic direction, focusing on long‑term growth, innovation, and leveraging new technologies.
• Compliance and Security: Uphold high standards in compliance, particularly focusing on data security and privacy in software development.
• Resource and Financial Management: Effectively manage the lab’s resources and budget to maximize efficiency and project success.

WHO WE’RE LOOKING FOR

• Bachelor’s or master’s degree in computer science, Engineering, or a related field.
• At least 10 years of senior leadership experience in software engineering managing large teams.
• Proven track record in leading teams to deliver innovative software solutions using AI.
• Proven ability to develop and implement strategic technical roadmaps in collaboration with product, architecture and various teams.
• Knowledge of industry standards and compliance requirements, especially in data security and privacy.
• Strong leadership and communication skills, with an ability to motivate and inspire teams.
• Experience with SaaS products, API development, microservices architecture and cloud computing.
• Familiarity with Agile methodologies and modern software development practices.

THE CULTURE

We believe a career should be meaningful. Not just a means to earn a living. Our culture is one where everyone’s voice is heard and valued. Because that’s what it takes to create better health for all. We dare to challenge the status quo. And we’re driven by people who have challenged theirs. We believe that your workplace should empower you to be the best version of yourself. That’s why we provide a place where you can be inspired, challenged, and rewarded.

Where your growth means our growth.

Where your voice is heard and valued.

Where your work has purpose. And purpose matters.

We believe our people are critical to our overall success. Inclusivity makes us a stronger, smarter and more informed organization. Being intentionally inclusive of diverse backgrounds, perspectives and experiences will enhance our company culture to positively impact how we support our communities. A career at GreenShield isn’t just about personal achievements, it’s about making a difference together.

Here’s to Better Health for All!

Proficiency in English is required for this position. As part of this role, you will be required to communicate with colleagues or customers who use English as their primary language. By requiring English proficiency for this position, we aim to ensure that our employees can excel in their roles, collaborate, and communicate effectively, and contribute to the success of our organization.

GS supports diversity, equity and inclusion in our teams and communities, and we value the unique contributions made by all. Even if your experience doesn’t align perfectly to every requirement, we invite you to apply. We encourage applications from all candidates and will accommodate needs under human rights legislation throughout all stages of the recruitment and selection process. Please let us know of any accommodation through requestforaccommodation@greenshield.ca. Information received relating to accommodation will be addressed confidentially.

Providing this information gives GS consent to use your personal information to assess your suitability for specific positions, future opportunities or for your personnel file. Your résumé will be held in strict confidence and will be viewed only by the Organization. Information may be stored outside of Canada and could be used for aggregate statistical purposes (which uses no personal identification).

AI Usage - At present, GS does not utilize AI in its selection process, though we do leverage AI to help produce Job Descriptions, and ideate on interview questions.

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