Manager Software Development, Observability Platform in Winnipeg

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.

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. Every request, job, and user action produces a signal, and our job is to turn that signal into a fast, high-cardinality data asset that anyone can question.

As the founding Software Development Manager for this team, you will hire and lead the engineers who build this foundation, and set the technical vision that shapes how Wealthsimple understands its systems for years to come.

In this role you'll have the opportunity to:

• Build the wide-event data model at the heart of the platform.
• Lead an events-first foundation on open standards such as OpenTelemetry.
• Connect production data to business impact.
• Define what observability means at Wealthsimple, set a multi-year roadmap, and align engineering and leadership behind it.
• Own the tool and vendor strategy across the observability stack.
• Prove value on pilots.
• Hire and lead the team, and own career development, performance management, coaching, and a culture of technical excellence.
• Stay hands-on, and move fast with AI coding tools.

What you'll bring:

• 7+ years in software engineering, with a software development background.
• Direct, hands‑on experience treating telemetry as a data problem.
• Direct experience building an observability, telemetry, or production-data platform.
• A track record of building SDKs and shared platforms.
• Fluency with OpenTelemetry or an equivalent.
• 3+ years of engineering management experience.
• Strong people leadership and cross‑boundary influence.

Nice to have:

• Experience with columnar stores such as ClickHouse, streaming systems such as Kafka.
• Experience building observability for LLM and agent‑based workloads.
• Familiarity with self‑serve data access, semantic layers, or data cataloging.
• Experience in a regulated or fintech environment.

Why Wealthsimple?

• Top-tier health benefits and life insurance.
• Long‑term group savings with employer match.
• 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.
• We are a hybrid team with over 1,500 employees across North America.

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.

AI in Hiring: We may use artificial intelligence (AI) tools to support parts of our hiring process.