Manager Software Development, Observability Platform

Location: Remote (Canada) Workplace: Remote 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 OBSERVABILITY PLATFORM TEAM 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. Every request, job, and user action produces a signal, and our job is to turn that signal into a fast, high-cardinality data asset that anyone can question. A business stakeholder investigating a drop in conversions, a service owner tracing a slow endpoint, an engineer validating a release, and an AI agent confirming its own change should all reach for the same data and get an answer in seconds. We treat the platform as a product, and the engineers, service owners, and business stakeholders who depend on it as our partners. Our mission is to build the wide-event data model, the query foundation, and the golden paths that connect people to production data. We instrument on open standards such as OpenTelemetry so switching costs are a configuration change rather than a rewrite, and we optimize for the questions people did not anticipate rather than for pre-built dashboards. As the founding Software Development Manager for this team, you will hire and lead the engineers who build this foundation, and set the technical vision that shapes how Wealthsimple understands its systems for years to come. IN THIS ROLE YOU'LL HAVE THE OPPORTUNITY TO: - Build the wide-event data model at the heart of the platform. Lead an events-first foundation on open standards such as OpenTelemetry, including the schema, SDKs, libraries, and instrumentation defaults that make rich, consistent, high-cardinality telemetry the path of least resistance for every team. - Build the query foundation that connects people to production data, and make it legible to AI agents. Design the columnar or streaming backends, the tagging and context-propagation standards, and the access patterns, including protocols such as MCP, that let a business stakeholder, a service owner, an engineer, or an AI agent ask an unanticipated question and get a fast answer. - Connect production data to business impact. Tie telemetry to client experience and business outcomes through SLOs and user flows, so teams see a problem in the numbers that matter before clients feel it. This is detection framed as a data question, not a wall of machine-state alerts. - Define what observability means at Wealthsimple, set a multi-year roadmap, and align engineering and leadership behind it. - Own the tool and vendor strategy across the observability stack, including how we get the most from Datadog while reducing lock-in and managing cost. - Prove value on pilots. Start with one or two teams to validate the approach before scaling it across the organization. - Hire and lead the team, and own career development, performance management, coaching, and a culture of technical excellence. - Stay hands-on, and move fast with AI coding tools such as Claude Code fluently to prototype, unblock the team, and raise its bar for building with AI. WHAT YOU'LL BRING: - 7+ years in software engineering, with a software development background. You build platforms as software, with the testing, design, and engineering rigor that implies. - Direct, hands-on experience treating telemetry as a data problem. You have designed wide structured events, managed high cardinality, and worked with columnar or streaming backends, sampling, tagging, and context propagation. This is the core of the role. - Direct experience building an observability, telemetry, or production-data platform before, so you are not learning the problem space on the job. You do not need to have built a commercial product such as Datadog or Honeycomb, but you have built the equivalent inside an engineering organization. - A track record of building SDKs and shared platforms in a platform, data, or foundations team. You have shipped the libraries, paved roads, and defaults that other engineers build on, and you treat those engineers as partners. - Fluency with OpenTelemetry or an equivalent, and with SLI and SLO design that ties signals to client experience and business outcomes. - 3+ years of engineering management experience, developing engineers and delivering complex initiatives through both growth and change. - The ability to set a vision, sequence the work, and move engineering and leadership toward it. - Strong people leadership and cross-boundary influence. You grow careers, give clear feedback, build inclusive teams, and build trust with peer managers, senior leadership, service owners, and business stakeholders. NICE TO HAVE: - Experience with columnar stores such as ClickHouse, streaming systems such as Kafka, or query engines built for high-cardinality analytics. - Experience building observability for LLM and agent-based workloads. - Familiarity with self-serve data access, semantic layers, or data cataloging that helps non-experts find and query the right signal. - Experience in a regulated or fintech environment. 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. *Unlimited paid sick days, Wellness Days and the 90 day away program do not apply to certain roles. 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.