[Hiring] Software Development Manager, Observability Platform @Wealthsimple Technologies

Role Description

As the founding Software Development Manager for the Observability Platform 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.

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, leading 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 using SLOs and customer-experience signals.
• Make production legible to AI agents by building the fast, high-cardinality query foundation and access patterns.
• Run experiments and prove value on pilots, establishing a test-and-learn approach.
• 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 coding when necessary.
• Move fast with AI tooling, using AI coding tools to prototype, build, and navigate large systems.

Qualifications

• 7+ years in software engineering, with a software development background.
• 3+ years of engineering management experience, developing engineers and delivering complex technical initiatives.
• Direct, hands-on experience building an observability or telemetry platform.
• Experience with event-based systems, including wide structured events and high-cardinality data.
• A track record of building SDKs and shared platforms in a platform or foundations engineering team.
• Fluency with open standards and instrumentation, including hands-on experience with OpenTelemetry.
• The ability to set a vision and a mission and move an organization toward it.
• Comfort running experiments, framing work as hypotheses to validate.
• Strong people leadership skills, including career growth and team inclusivity.
• Collaboration and influence across boundaries, building trust with peer managers and senior leadership.

Requirements

• Experience in a regulated or fintech environment.
• Familiarity with Kubernetes and progressive delivery such as Argo Rollouts.
• Experience with columnar stores such as ClickHouse.
• 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.
• Hybrid team with over 1,500 employees across North America.