Senior Software Engineer in Winnipeg

About ComPsych

ComPsych is the worldwide leader in organizational mental health, well-being, and absence management, dedicated to igniting human potential in workplaces across the globe. For over 40 years, we have combined the best in technology with unmatched human expertise to help individuals and their organizations thrive. Our GuidanceResources and AbsenceResources solutions deliver end-to-end mental health, well-being, work-life, health navigation, and absence support to more than 75,000 customers worldwide, touching more than 160 million lives across 200 countries.

About the Role

We're modernizing how ComPsych builds technology - new customer-facing web and mobile experiences, a unified design system, and AI-powered capabilities across our products. That means raising the engineering bar for how we design, build, and operate software, with Engineering, Product, and Design working together end to end.

We're looking for a Senior Software Engineer who has hands-on experience with modern, AI-led development practices and wants to help shape how our engineering organization builds software going forward. This is a high-leverage role: you'll spend more time on system design, task decomposition, and technical direction than on writing code line-by-line. You'll use AI tools to generate code, automated tests, and first-pass reviews, then apply your own judgment to validate and refine that output before it ships.

What You'll Do

• Plan and design as your core contribution.
• You own problem framing, sequencing, and tradeoffs with Product and Design, and the system design that follows - the data model, the API contracts, the failure modes.
• Direct implementation rather than writing it line by line.
• Decompose the work, write the specs, and let AI agents build - dropping into the code yourself when debugging or complexity demands it.
• Own testing as a design decision.
• You decide what needs coverage and at what level, direct AI to build it, and validate that the tests prove what they claim - not just that they pass.
• Build security, reliability, and observability in from the start.
• Review everything with the same rigor, regardless of author, and keep production judgment human.
• Raise the bar for how the team works with AI, coaching engineers to specify, delegate, and validate rather than hand-code everything themselves.

What We're Looking For

• Deep server-side experience in a modern language such as Java, Python, C#, Kotlin, or Go.
• Must have 5+ years of full stack development experience.
• APIs and data models other people depend on: REST contracts, versioning, OAuth2/OIDC, schema design, and SQL that holds up under real load.
• Async and event-driven systems in production - Kafka or comparable, idempotency, and a clear view of what at-least-once costs you downstream.
• You've built and operated production systems at real scale on AWS or Azure - containers, Kubernetes or serverless, IaC, and CI/CD pipelines you've built, operated, or materially improved.
• A testing strategy you can defend - what belongs at unit, integration, and contract level, and how you know a release is verifiable before it ships.
• Reliability and security you've been accountable for: SLOs you've been paged against, incidents you led, OWASP and threat modeling applied.
• Agentic AI is your primary development surface, and you catch what it gets subtly wrong.

Bonus: LLM application engineering (RAG, retrieval quality, evals, LLM observability), or modern TypeScript frontend work against a design system.

Pay Range: USD $150,000.00 - USD $200,000.00 /Yr.

Compensation and Benefits

Full benefits package, including Paid Time Off (PTO), medical, dental, vision, 401(k) with match, robust EAP, wellness program, and much more.

The salary range for this position is 200,000 - 275,000 (CAD). The base salary range represents the anticipated low end and high end of the range for this position. The actual compensation will be influenced by a wide range of factors including, but not limited to previous experience, education, pay market/geography, and scheduled hours.

EEO

ComPsych is an equal opportunity employer. All applicants will be considered for employment regardless of race, color, age, genetics, religion, gender, sexual orientation, gender identity, national origin, disability or protected veteran status and any other characteristic protected by federal, state or local laws.