Software Development Manager, Observability Platform

Wealthsimple Technologies • ,

1d • Hybrid

About The Position

As the founding Software Development Manager for the Observability Platform team, you will hire and lead the engineers who build the foundation for making production legible to every engineer and AI agent at Wealthsimple. You will set the technical vision that shapes how Wealthsimple understands its systems for years to come. The Observability Platform team treats the platform as a product, with internal engineering teams as customers. Their mission is to provide the best, most consistent logging, metrics, and tracing experience 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. They instrument on open standards, optimize for anticipated questions, and design for a world where humans and AI agents investigate production through fast, high-cardinality data.

Requirements

• 7+ years in software engineering, with a software development background rather than a primarily operations or systems-administration one.
• 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.
• Experience with event-based systems, including understanding wide structured events, high-cardinality data, columnar or streaming backends, sampling, tagging, and context propagation.
• A track record of building SDKs and shared platforms in a platform or foundations engineering team.
• Fluency with open standards and instrumentation, with hands-on experience with OpenTelemetry or an equivalent, and with SLI and SLO design.
• The ability to set a vision and a mission and move an organization toward it.
• Comfort running experiments, being data-informed, framing work as hypotheses to validate, and willingness to pilot, measure, and adjust.
• Strong people leadership skills, including growing careers, giving clear feedback, building inclusive teams, and attracting and retaining strong engineers.
• Collaboration and influence across boundaries, building trust with peer managers, senior leadership, and partner teams, and communicating clearly to technical and non-technical audiences.

Nice To Haves

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

Responsibilities

• Lead an impactful team with a lot of visibility, owning 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.
• Build the wide-event data model and the golden paths on top of it, leading the design of an events-first foundation on open standards such as OpenTelemetry, including shared SDKs, libraries, and instrumentation defaults.
• Drive the company's detection and reliability goals, leading work that reduces mean time to detect on key user flows using SLOs and customer-experience signals.
• Make production legible to AI agents by building the fast, high-cardinality query foundation and access patterns, including protocols such as MCP.
• Run experiments and prove value on pilots, establishing a test-and-learn approach to validate the approach before scaling it across the organization.
• Own the tool and vendor strategy, shaping build, buy, and broker decisions across the observability stack.
• Stay hands-on by contributing to critical architectural decisions, reviewing complex designs, and getting into the code when necessary.
• Move fast with AI tooling, using 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.

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

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed