Staff Software Engineer, Observability Platform

Portage Ventures GP Inc.; United States; Hybrid; USD 130,000 - 170,000; Full time

Benefits offered by this job

Health benefits

Life insurance

Vacation days

Wellness days

Unlimited sick days

Hybrid team

Employee resource groups

Job summary

Wealthsimple is seeking a Staff Software Engineer for the Observability Platform Team. You will design the events-first foundation, build instrumentation libraries and SDKs, and set standards for open-standards instrumentation to enable production systems to be legible for humans and AI alike.

You will mentor engineers, collaborate across teams, and push high-impact improvements in telemetry, data processing, and incident investigation, while working in a hybrid setup across North America.

Qualifications

• At least 8 years of software engineering experience building platforms and tools.
• Hands-on coding in Kotlin and Ruby with production code delivery.
• Experience with observability/telemetry platform and its SDKs.
• Deep knowledge of event-based, high-cardinality systems and backends.
• Familiarity with OpenTelemetry and SLI/SLO design.
• Experience using AI coding tools and LLMs in daily workflows.
• Strong collaboration and influence across engineering teams.

Responsibilities

• Design and build the events-first foundation, data model, and high-throughput pipelines.
• Develop instrumentation libraries, shared SDKs, and defaults for consistent telemetry.
• Define instrumentation conventions and context propagation on OpenTelemetry or similar.
• Create fast query foundations enabling AI agents to investigate incidents efficiently.
• Leverage AI tooling to prototype and accelerate large system development.
• Navigate ambiguous codebases, make high-impact changes, and mentor others.
• Lead cross-team technical initiatives with influence over outcomes.

Skills

8+ years software engineering

Kotlin

Ruby

OpenTelemetry

AI tooling (Claude Code)

Strong communication

Tools

Instrumentation libraries

SDKs

Streaming/columnar backends

Job description

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 $125 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 and learn more about how we work.

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 Staff Software Engineer on this team, you are the deepest technical builder and the person who sets the technical bar. You design the foundations, write the code that matters most, and raise the engineering quality of everyone around you.

In this role you'll have the opportunity to:

• Design and build the events-first foundation. Own the architecture of the wide-event data model and the high-throughput ingest, storage, and query pipelines behind it, including the high-cardinality and columnar or streaming systems that make arbitrary questions answerable in production.

• Build the SDKs and golden paths. Design and ship the instrumentation libraries, shared SDKs, and defaults that make rich, consistent telemetry the path of least resistance for every engineering team, and drive their adoption.

• Set the technical standards. Define the instrumentation conventions, naming, tagging, sampling, and context-propagation practices on open standards such as OpenTelemetry, and codify them so humans and machines share one language.

• Make production legible to AI agents. Build the fast query foundation and access patterns, including protocols such as MCP, that let AI agents investigate incidents, verify their own changes, and operate in tight feedback loops alongside engineers.

• Move fast with AI tooling. Use 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.

• Work confidently in ambiguity. Jump into unfamiliar codebases and make significant, well-reasoned changes with high impact.

• Prove value through experiments. Pilot new approaches with one or two teams, measure the results, and scale what works rather than committing everything up front.

• Raise the bar for others. Mentor senior engineers, review complex designs, and lead cross-team technical initiatives through influence rather than authority.

What you'll bring:

• Significant software engineering experience, typically 8+ years, with a software development background rather than a primarily operations or systems-administration one. You build platforms and tools as software, with the design, testing, and engineering rigor that implies.

• A hands-on, current coder in more than one language such as Kotlin and Ruby. You are comfortable across multiple stacks, and you still spend meaningful time writing and shipping production code.

• Direct experience building an observability or telemetry platform and its SDKs before. You have shipped the instrumentation libraries, pipelines, and shared platforms that other engineers build on, and you carry the deep technical expertise this team is founded on.

• Depth in event-based and high-cardinality systems. You understand wide structured events, columnar or streaming backends, cardinality, sampling, tagging, and context propagation, and the tradeoffs of ingesting and querying telemetry at scale.

• Fluency with open standards and instrumentation. Hands-on experience with OpenTelemetry or an equivalent, and with SLI and SLO design, is core to how you work.

• Comfort making significant changes in ambiguous codebases. You can enter a system you did not build, form an accurate model of it quickly, and change it safely and substantially.

• Proficiency with AI coding tools and LLMs. You use tools such as Claude Code fluently in your daily workflow, you have a clear point of view on where they help and where they do not, and you keep quality high while moving faster.

• Strong communication and influence. You partner well with other engineering teams, explain complex tradeoffs clearly, and improve the systems and the people around you.

Nice to have:

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