Senior Software Developer, Delivery Platform at Wealthsimple – Canada | Jobyssey

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 and learn more about how we work.

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 concepts to diverse audiences and building consensus across teams.
Data-informed decision-making. You use metrics to identify opportunities, measure impact, and guide technical decisions. You're comfortable establishing baselines, setting targets, and tracking progress toward goals.

Why Wealthsimple?

🌸 Top-tier health benefits and life insurance

📈 Long-term group savings with employer match, through Wealthsimple for Business

🌴 20 vacation days, 4 wellness days, and unlimited sick and mental health days per year

✈️ 90 days away: work outside Canada for up to 90 days per year

👥 Employee resource groups, including Rainbow (2SLGBTQ), Women of WS, and Black at WS

🌎 We are a hybrid team with over 1,500 employees across North America. The people are one of the best parts of working here: you'll collaborate with incredibly talented, curious, and driven teammates who are deeply committed to doing great work.

ICYMI

Technology & Innovation at Wealthsimple: We move quickly and build thoughtfully. That means we're always looking for better ways to work — whether that's new tools, AI, or rethinking how we approach a problem. We don't expect you to have all the answers, but we do expect curiosity and a willingness to evolve alongside the products we're building.

Inclusion Statement: We're building products for a diverse world, and we need a diverse team to do it well. We strongly encourage applications from everyone, regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

Accessibility Statement: We're committed to an accessible hiring experience. If you need any accommodations throughout the interview process, please let us know — we'll work with you to make sure you have what you need. We also welcome any feedback on how we can better accommodate candidates with accessibility needs.

AI in Hiring: We may use artificial intelligence (AI) tools to support parts of our hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our team but don't replace human judgment – all final hiring decisions are made by people. If you have questions about how your data is used, reach out to us.

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