Software Development Manager, Observability Platform

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 $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 founding Software Development Manager for this team, you'll hire and lead the engineers who build that foundation, and you'll set the technical vision that shapes how Wealthsimple understands its systems for years to come.

• Lead an impactful team with a lot of visibility. You'll own career development, performance management, coaching, and a culture of technical excellence, collaboration, and continuous improvement.

• Define what observability means at Wealthsimple, articulate a multi-year roadmap, and align engineering and leadership behind it. You turn a vision into a sequenced plan and then into shipped platform capabilities.

• Build the wide-event data model and the golden paths on top of it. Lead the design of an events-first foundation on open standards such as Open Telemetry, including the shared SDKs, libraries, and instrumentation defaults that make rich, consistent telemetry the path of least resistance for every team.

• Drive the company's detection and reliability goals. Lead the work that reduces mean time to detect on key user flows, using SLOs and customer-experience signals that catch issues before customers feel them, rather than alerts that only report machine state.

• Make production legible to AI agents. Build the fast, high-cardinality query foundation and the access patterns, including protocols such as MCP, that let AI agents investigate incidents, verify their own changes, and operate in tight feedback loops alongside engineers.

• Run experiments and prove value on pilots. Establish a test-and-learn approach, starting with one or two pilot teams to validate the approach before scaling it across the organization.

• Own the tool and vendor strategy. Shape the build, buy, and broker decisions across the observability stack, including how we get the most from Datadog while reducing lock-in and managing cost.

• Stay hands-on. Contribute to critical architectural decisions, review complex designs, and get into the code when it will unblock the team or prototype a new approach.

• Move fast with AI tooling. Use AI coding tools such as Claude Code and modern LLMs fluently to prototype, build, and navigate large systems, and help the team raise its own bar for building with AI.

• 7+ years in software engineering, with a software development background rather than a primarily operations or systems-administration one. You build platforms and tools as software, with the testing, design, and engineering rigor that implies.

• 3+ years of engineering management experience, developing engineers and delivering complex technical initiatives through both…