wealthsimple - Software Development Manager, Observability Platform
Requirements
• 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 growth and change. • Direct, hands-on experience building an observability or telemetry platform before. You have implemented this kind of roadmap at least once, 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 or implemented the equivalent capability inside an engineering organization. • Experience with event-based systems. You understand wide structured events, high-cardinality data, columnar or streaming backends, sampling, tagging, and context propagation, and why these matter for asking questions you did not anticipate. • A track record of building SDKs and shared platforms in a platform or foundations engineering team. You have shipped the libraries, paved roads, and defaults that other engineers build on, and you treat those internal engineers as customers. • Fluency with open standards and instrumentation. Hands-on experience with OpenTelemetry or an equivalent, and with SLI and SLO design, is core to how you think. • The ability to set a vision and a mission and move an organization toward it. You can define direction, sequence the work, and bring engineering and leadership along. • Comfort running experiments. You are data-informed, you frame work as hypotheses to validate, and you are willing to pilot, measure, and adjust rather than commit everything up front. • Strong people leadership. You grow careers, give clear feedback, build inclusive teams, and attract and retain strong engineers. • Collaboration and influence across boundaries. You build trust with peer managers, senior leadership, and partner teams, and you communicate clearly to technical and non-technical audiences. • Experience in a regulated or fintech environment, familiarity with Kubernetes and progressive delivery such as Argo Rollouts, experience with columnar stores such as ClickHouse, and experience building observability for LLM and agent-based workloads.
Benefits
• 🌸 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.
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