Aimed at mid-level software development managers with hands-on observability platform experience and a track record of building SDKs in remote Canadian settings.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Wealthsimple via Ashby
BUILD SOMETHING PEOPLE LOVE
Wealthsimple is Canada’s leading financial innovator. The company offers 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 $155 billion in assets under administration. The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada.
We're proud of what we've built — and we're just getting started. Read our Culture Manual https://www.wealthsimple.com/en-ca/culture and learn more about how we work https://www.wealthsimple.com/en-ca/careers.
ABOUT THE OBSERVABILITY PLATFORM TEAM
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.
IN THIS ROLE YOU'LL HAVE THE OPPORTUNITY TO:
- 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.
- AI-Native Production & Tooling:
- 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.
WHAT YOU BRING
- Engineering Experience: 7+ years in software development (building platforms as software, not pure sysadmin/ops) + 3+ years in Engineering Management.
- 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.
- Strategic & Technical Leadership: Ability to set a vision, run experimental pilots, stay hands-on with architecture, and influence across teams.
- People Management: Proven ability to coach, retain talent, and build inclusive, high-performing teams.
NICE TO HAVE
- Fintech/regulated industry background.
- Kubernetes, Argo Rollouts, or ClickHouse experience.
- Observability for LLM/AI-agent workloads.
WHY WEALTHSIMPLE?
🌸 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.
ICYMI
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.
Source: Wealthsimple careers (Ashby)