Staff Software Engineer, Observability Platform

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 $125 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.

The Observability Platform team exists to make production legible to every engineer and AI agent at Wealthsimple, on their first day and every day after. We treat the platform as a product, with our internal engineering teams as our customers.

Our mission is to provide the best, most consistent logging, metrics, and tracing experience. We do this by brokering tools and patterns into golden paths that accelerate best practices, and by connecting teams to business impact through SLOs, user flows, and customer experience signals. We instrument on open standards so that switching costs are a configuration change rather than a rewrite, we optimize for the questions engineers did not anticipate rather than for pre-built dashboards, and we design for a world where both humans and AI agents investigate production through fast, high-cardinality data.

As the Staff Software Engineer on this team, you are the deepest technical builder and the person who sets the technical bar. You design the foundations, write the code that matters most, and raise the engineering quality of everyone around you.

• Build the Event Foundation: Own the architecture for wide-event data models, high-cardinality storage, and high-throughput ingestion and query pipelines (columnar/streaming).

• Craft SDKs & Golden Paths: Design, ship, and drive adoption for telemetry libraries and SDKs that make rich instrumentation the path of least resistance.

• Set Technical Standards: Define instrumentation conventions, naming, tagging, sampling, and OpenTelemetry standards so humans and machines speak one language.

• Enable AI Agents in Production: Build fast query foundations and access patterns (e.g., Model Context Protocol / MCP) that allow AI agents to investigate incidents and verify changes alongside engineers.

• Build Fast with AI: Leverage modern AI tools (like Claude Code) to prototype, navigate complex systems, and help elevate the team’s AI-assisted workflows.

• Navigate Ambiguity: Dive into unfamiliar codebases to deliver significant, well-reasoned, high-impact changes safely.

• Experiment & Scale: Pilot new approaches with select teams, measure impact, and scale what works before committing broadly.

• Raise the Technical Bar: Mentor senior engineers, review complex architecture, and lead cross-team technical initiatives through influence.

• 8+ Years in Software Engineering: Strong software background (building platforms as software) rather than pure Ops/SysAdmin.

• Multi-Language Coder: Current, hands-on experience writing production code in multiple languages (e.g., Kotlin, Ruby).

• Proven Telemetry Experience: Prior success building telemetry platforms, ingestion pipelines, and developer-facing SDKs.

• Event & Scale Mastery: Deep understanding of wide structured events, streaming/columnar backends, cardinality, sampling, and context propagation.

• Open Standards Expert: Hands-on experience with OpenTelemetry (or equivalent) and designing SLIs/SLOs.

• System Navigator: Ability to quickly map out, safely refactor, and impact complex, ambiguous codebases you didn't originally build.

• AI-Fluent Developer: Daily proficiency with AI tools (like Claude Code) to move faster while maintaining high quality standards.

• Strong Influencer: Exceptional communication skills to partner with cross-functional engineering teams and explain complex tradeoffs clearly.

• Experience in fintech or regulated environments.

• Hands-on experience with ClickHouse or columnar stores.

• Exposure to Kubernetes and progressive delivery tools (e.g., Argo Rollouts).

• Experience building observability solutions specifically for LLM and agent-based workloads.

🌸 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.

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.