Staff Engineer

GreenShield; Toronto; On-site; CAD 150,000 - 210,000; Full time

Job summary

GreenShield, a not-for-profit health and benefits company, is seeking a Staff Engineer in Toronto to lead solution design, architecture, and reliable service operations across the digital health ecosystem. This individual contributor leadership role emphasizes clarification of ambiguous problems, technical direction, and mentoring engineers to improve practices and decisions across teams.

You will shape technical direction, runbooks, and production readiness while partnering with Product,

Qualifications

• 10+ years building and operating software systems across web apps, APIs, and cloud environments.
• Strong full stack experience with TypeScript, Node.js, React, PostgreSQL, and RESTful APIs.
• Experience with GCP, NestJS, NextJS is an asset; broader technical judgement is valued.
• Proven ability to lead complex initiatives from architecture to production ownership.
• Excellent communication and collaboration across product, design, data, security, and ops.

Responsibilities

• Lead solution design and architecture for complex full stack systems balancing customer impact and platform health.
• Own technical outcomes through production including observability, incident response, and reliability.
• Align technical direction across teams and surface risks early in projects.
• Define success with measurable metrics and instrument systems to guide decisions.
• Drive improvements to API design, testing, CI/CD, cloud infra, and developer workflows.
• Mentor engineers across levels and raise the overall quality of technical discussions.

Skills

TypeScript

Node.js

React

PostgreSQL

RESTful APIs

Cloud platforms

GCP

NestJS

NextJS

Leadership

Education

Bachelor's or Master's in CS/CE/SE

Tools

Cloud platforms

Observability

Job description

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

As a Staff Engineer, you will be a technical leader responsible for solution design, architecture, and the reliable operation of services across the digital health ecosystem. You will work across teams, products, and lines of business to make sure important decisions are coherent, scalable, and grounded in the needs of members and customers.

This is an individual contributor leadership role. Writing code remains part of the work, but your highest-leverage contribution will often be clarifying ambiguous problems, shaping technical direction, mentoring engineers, improving engineering practices, and helping teams make better decisions earlier.

You will operate in an environment that values ownership, high standards, and reliable service. Staff engineers are expected to take responsibility for outcomes, not just output. You will follow important problems through to resolution, especially when they become difficult, cross team boundaries, or expose deeper system design issues.

Responsibilities:

• Lead solution design and architecture for complex full stack systems, balancing customer impact, operational risk, delivery speed, maintainability, and long-term platform health.
• Own technical outcomes through production, including system behavior, observability, incident response, performance, reliability, maintainability, and continuous improvement.
• Work across teams to align technical direction, clarify ownership, identify dependencies, and ensure GreenShield's digital health services evolve as a coherent ecosystem.
• Define success in measurable terms. Establish metrics, instrument systems, and use data to guide decisions, evaluate trade-offs, validate assumptions, and improve outcomes.
• Raise the bar for operational excellence through strong logging, metrics, alerts, dashboards, SLOs, runbooks, production readiness practices, and disciplined follow-up after incidents.
• Lead technical discovery and planning for ambiguous or high-impact initiatives, including requirements clarification, estimates, risks, trade-offs, architecture options, and execution plans.
• Drive improvements to API design, automated testing, CI/CD, cloud infrastructure, data flows, service reliability, and developer workflows.
• Identify and remove unnecessary complexity in systems, workflows, dependencies, and team processes so teams can deliver faster and more safely.
• Partner effectively with Product, Design, Data, Security, Operations, and engineering leadership to align on goals, surface risks early, and make trade-offs explicit.

WHO WE'RE LOOKING FOR

• 10+ years of experience building and operating software systems, with significant experience across modern web applications, backend services, APIs, databases, cloud environments, and production operations.
• Bachelor's or Master's degree in Computer Science, Computer Engineering, Software Engineering, a related field, or equivalent practical experience.
• Strong full stack engineering experience with technologies such as TypeScript, Node.js, React, PostgreSQL, RESTful APIs, and cloud platforms. Direct experience with GCP, NestJS, NextJS, or similar technologies is an asset, but broader technical judgment is more important than exact stack match.
• Demonstrated experience delivering and operating customer-facing systems at meaningful scale, with accountability for reliability, quality, security, performance, and customer experience.
• Proven ability to lead complex technical initiatives across teams, from problem definition and architecture through implementation, launch, and production ownership.
• Strong technical judgment and the ability to make decisions using evidence. You define metrics, instrument systems, analyze production behavior, and adjust based on what the data shows.
• Deep commitment to operational excellence. You build systems that are observable, reliable, maintainable, and able to operate under real-world conditions.
• Strong customer focus, with a track record of measuring success by the experience delivered rather than the amount of work produced.
• Demonstrated ability to mentor and coach senior, intermediate, and junior engineers while raising the quality of technical discussion and execution across the team.
• Excellent communication and collaboration skills, with the ability to influence cross-functional partners and align teams around clear goals, trade-offs, risks, and decisions.

Working Style:

You succeed in this role if you see Staff Engineering as a technical leadership path, not simply a more senior coding role. You are energized by systems that matter, customers who depend on them, and teams that care about raising the bar. You consistently prioritize mentorship and continuous improvement. You are willing to go deep, challenge assumptions with evidence, and stay engaged until the problem is truly resolved.

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.

AI Usage - GreenShield leverages AI to help produce Job Descriptions, and ideate on interview questions. We also leverage AI for interview transcription support.