Senior Software Developer, Delivery Platform

About this role

BUILD SOMETHING PEOPLE LOVE

Wealthsimple is Canada’s leading financial innovator. The company offers a full suite of simple, sophisticated financial products across managed investing, do-it-yourself trading, cryptocurrency, tax filing, spending and saving. Wealthsimple currently serves more than 4 million Canadians and holds over $155 billion in assets under administration. The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada.

We're proud of what we've built — and we're just getting started. Read our Culture Manual https://www.wealthsimple.com/en-ca/culture and learn more about how we work https://www.wealthsimple.com/en-ca/careers.

ABOUT THE DELIVERY PLATFORM TEAM

The Delivery Platform team owns the complete deployment lifecycle at Wealthsimple. From the moment code is committed to when it's running reliably in production. We build and maintain the CI/CD infrastructure, deployment systems, and observability tools that enable hundreds of engineers to ship secure, high-quality software to millions of users with confidence and speed.

Our platform encompasses GitHub Actions self-hosted runners for continuous integration, Kargo, ArgoCD and Argo Rollouts for progressive delivery with canaries and automated rollbacks, package publishing and artifact promotion, deployment visibility through Datadog and Backstage. We treat reliability as our north star and deployment velocity as our measure of success.

As a Senior Developer on our team, you won't just be maintaining pipelines; you'll be architecting the systems that make shipping code at Wealthsimple fast, safe, and transparent. You will support a diverse engineering organization that uses Ruby, Python, Kotlin, and TypeScript to build the future of finance. Your work will directly empower hundreds of developers to deploy with confidence many times per day.

IN THIS ROLE YOU'LL HAVE THE OPPORTUNITY TO:

- Evolve progressive delivery with Argo Rollouts and GitOps. Enhance our canary deployment strategies, improve automated health checks and rollback triggers, and build self-service deployment tools that give engineering teams the power to ship safely and independently. You'll work directly with Kubernetes, ArgoCD, and Argo Rollouts to make deployments invisible when they work and obvious when they don't.

- Optimize CI/CD infrastructure at scale. Improve our CI workflows to optimize for speed and reliability, optimize build times across hundreds of services, enhance artifact management and package publishing workflows, and build tools that make continuous integration faster and more dependable.

- Build deployment gates and guardrails that prevent production incidents. Design and implement automated quality checks including end-to-end testing, load testing, and progressive delivery validations that catch issues before they reach production. You'll be responsible for ensuring every deployment is safe and reversible.

- Build world-class deployment observability and visibility. Create comprehensive deployment monitoring, dashboards, and alerting through Datadog and custom tooling. Integrate deployment metrics into Backstage to give every engineer real-time insights into their service's deployment health, success rates, and performance characteristics.

- Drive Wealthsimple's 2026 reliability mission. Reliability is our top priority this year, and you'll be at the center of building systems that make it a reality. Implement chaos testing frameworks to validate system resilience, build automated rollback mechanisms, and create deployment confidence metrics that teams can trust.

- Champion engineering excellence and mentorship. Partner with teams across Wealthsimple to understand their deployment pain points and build solutions that increase their velocity. Share your expertise through documentation, training sessions, and code reviews. Mentor mid-level engineers on the team and across the organization.

WHAT YOU'LL BRING:

- 7+ years of experience in software development as part of a team, with significant experience in platform engineering, DevOps, CI/CD, or site reliability engineering.

- Deep expertise with modern deployment and orchestration technologies. Hands-on experience with Kubernetes, GitOps workflows (ArgoCD or similar), progressive delivery patterns, and managing CI/CD infrastructure at scale. You understand canary deployments, blue-green strategies, and automated rollback mechanisms.

- Strong experience building and operating deployment pipelines. You've designed, built, and maintained CI/CD systems using tools like Buildkite, GitHub Actions, Jenkins, GitLab CI, or similar. You know how to optimize build times, manage artifacts, and ensure pipeline reliability.

- Expertise in reliability engineering and observability. Experience building observable systems with monitoring platforms like Datadog, Prometheus, or similar. You understand SLIs, SLOs, error budgets, and how to build systems that are measurable and resilient.

- Technical versatility with multiple languages. Experience with TypeScript, Ruby, Python, Kotlin, or similar languages. You're comfortable writing tooling, automation, and infrastructure code across different technology stacks.

- Infrastructure as code and cloud platforms. Experience with AWS, Terraform, or similar infrastructure automation tools. You know how to build and maintain infrastructure that's reproducible, version-controlled, and scalable.

- Product mindset for internal platforms. You treat deployment infrastructure as a product, with internal developers as your customers. You're driven to understand their pain points, measure the impact of your work, and build elegant solutions that make their lives better.

- A collaborative spirit and passion for mentorship. You believe in making your colleagues successful and enjoy coaching other developers. You're comfortable presenting technical…