Manager Software Development, Observability Platform

Wealthsimple is Canada’s leading financial innovator, offering 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.

About The Observability Platform Team: The Observability Platform team exists to make production legible to every engineer and AI agent at Wealthsimple. Our mission is to provide the best, most consistent logging, metrics, and tracing experience. We treat the platform as a product, with our internal engineering teams as our customers.

In this role you'll have the opportunity to:

• Lead an impactful team with a lot of visibility, owning career development, performance management, coaching, and fostering 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.
• 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 OpenTelemetry.
• Drive the company's detection and reliability goals, reducing mean time to detect on key user flows.
• Make production legible to AI agents by building the fast, high-cardinality query foundation.
• Run experiments and prove value on pilots, establishing a test-and-learn approach.
• Own the tool and vendor strategy, shaping decisions across the observability stack.
• Stay hands-on, contributing to critical architectural decisions and reviewing complex designs.
• Move fast with AI tooling, using AI coding tools to prototype and build large systems.

What you'll bring:

• 7+ years in software engineering, with a software development background.
• 3+ years of engineering management experience.
• Direct, hands-on experience building an observability or telemetry platform.
• Experience with event-based systems and a track record of building SDKs and shared platforms.
• Fluency with open standards and instrumentation.
• The ability to set a vision and move an organization toward it.
• Comfort running experiments and being data-informed.
• Strong people leadership skills.
• Collaboration and influence across boundaries.

Nice to have:

• Experience in a regulated or fintech environment.
• Familiarity with Kubernetes and progressive delivery.
• Experience with columnar stores and building observability for LLM and agent-based workloads.

Why Wealthsimple?

• Top-tier health benefits and life insurance.
• Long-term group savings with employer match.
• 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.
• A hybrid team with over 1,500 employees across North America.

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.

AI in Hiring: We may use artificial intelligence (AI) tools to support parts of our hiring process. All final hiring decisions are made by people.