Manager of Software Development (Observability Platform)

• 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. We treat the platform as a product, with our internal engineering teams as our customers
• Our mission is to provide the best, most consistent logging, metrics, and tracing experience. We do this 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
• We instrument on open standards so that switching costs are a configuration change rather than a rewrite, we optimize for the questions engineers did not anticipate rather than for pre-built dashboards, and we design for a world where both humans and AI agents investigate production through fast, high-cardinality data
• As the founding Software Development Manager for this 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
• Team Leadership & Culture: Manage, coach, and grow an impactful engineering team. Drive performance, career development, continuous improvement, and technical excellence
• Vision & Roadmap: Define Wealthsimple’s multi-year observability roadmap. Align engineering and leadership to turn big ideas into shipped platform capabilities
• Open-Standard Data Foundations: Build a wide-event data model and golden paths using OpenTelemetry. Deliver shared SDKs, libraries, and instrumentation defaults that make rich telemetry the default for every team
• Reliability & SLOs: Drive detection and reliability goals. Focus on customer-experience signals and SLOs to drop MTTR on key flows—catching issues before users ever feel them
• Build fast, high-cardinality query foundations and access patterns (e.g., MCP) so AI agents can investigate incidents and operate alongside engineers
• Leverage modern AI tools (e.g., Claude Code, LLMs) to prototype quickly and elevate the team’s engineering bar
• Test-and-Learn Execution: Validate concepts through pilots with 1–2 teams before rolling them out across the broader organization
• Vendor & Tooling Strategy: Direct build vs. buy vs. broker decisions across the stack, maximizing value from tools like Datadog while controlling costs and reducing lock-in
• Hands-On Architecture: Stay in the code when needed to unblock teams, prototype new approaches, and review complex designs

Benefits

• Retirement savings matching plan through Wealthsimple Work
• Company equity for full-time employees
• Access to Premium Client perks, including personal finance learning & advice and a boosted interest rate on deposits
• Paid parental leave (6 months topped up to 100% of salary)
• 20 vacation days per year
• 90 Days Away program
• Top-tier health benefits
• Life & disability insurance
• Generous sick and mental health days
• Employee resource plan including services like RMT, psychology, and physiotherapy
• Gender Affirmation benefits
• Up to $5,000 per year for mental health supports
• Up to $1,500 per year for professional development
• Up to $1,500 per year for wellness and home office expenses
• Employee resource groups
• Social impact hours

• Domain Expertise: Direct experience building/implementing an in-house observability platform (wide structured events, high-cardinality data, sampling, context propagation)
• Platform & Standards: Track record of shipping developer SDKs/libraries and applying OpenTelemetry (or equivalent) alongside SLI/SLO design
• Engineering Experience: 7+ years in software development (building platforms as software, not pure sysadmin/ops) + 3+ years in Engineering Management
• People Management: Proven ability to coach, retain talent, and build inclusive, high-performing teams
• Strategic & Technical Leadership: Ability to set a vision, run experimental pilots, stay hands-on with architecture, and influence across teams
• Observability for LLM/AI-agent workloads
• Fintech/regulated industry background
• Kubernetes, Argo Rollouts, or ClickHouse experience