Senior Software Developer - STAR

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 and learn more about how we work.

STAR sits inside the Book of Record (BOR), the ledger of truth for every dollar that moves through Wealthsimple. STAR stands for Statements, Tax slips, and Revenue: the outputs that make what's in the ledger visible and legally defensible. Our team runs 20M+ monthly client statements, tax slips filed across three tax authorities in North America, processing government grants, and the interest and fee calculations for all of our clients. STAR is a partner on every new product launch, making sure clients get correct, timely reporting and tax documents no matter what the rest of Wealthsimple ships.

We're a small team of 7 developers holding meaningful scope across a mix of Ruby services, Python data pipelines (including PySpark), and Airflow orchestration. If you like problems where correctness and compliance matter, and where the systems have to hold up at scale, you'll feel at home here.

• Design, build, and operate the pipelines and services that generate millions of statements, fees and interest payouts, and every tax slip we file

• Set architectural direction for how we build in this domain: proposing designs, guiding tradeoffs, and helping the team make consistent choices across services and pipelines

• Own significant scope end-to-end, from technical design to running your work reliably in production and standing behind it during regulatory deadlines

• Evolve our data architecture to improve accuracy, scale, and consistency across all client-facing outputs, moving us toward a single source of truth

• Raise the bar on quality through code review, testing frameworks, and design conversations that catch issues before they reach clients or regulators

• Mentor and grow the developers around you through pairing, code review, and in-the-moment feedback

• Shape how we build with AI-assisted tooling, holding the same rigor and quality bar we hold for our own work

• 7+ years of backend engineering experience building and operating scalable production systems, with a track record of accountability during peak load or high-consequence deadlines

• Strong system design and architectural judgment: you make sound trade-off calls, communicate them clearly, and can hold the shape of a system in your head across services and pipelines

• Strong data engineering skills at scale, including experience with distributed compute (Spark or comparable) and data pipeline design, plus solid Postgres experience, comfortable designing schemas and queries that can serve bulk data reliably to clients at scale

• Comfort working across Ruby, Python, and workflow orchestration (Airflow or equivalent); depth in one and willingness to ramp on the others matters more than an exact stack match

• Enthusiasm for AI-assisted development, with the engineering judgment to review, understand, and hold quality on what those tools produce

• Experience in fintech, banking, brokerage, or another regulated domain

• Familiarity with tax reporting, statement generation, ledgers, or other financial-correctness systems

• Exposure to interaction with government or regulatory bodies

• Familiarity with medallion architecture, dbt, or other structured data modelling approaches

• You take ownership end-to-end, especially during peak deadlines and high-stakes delivery windows

• You care deeply about correctness, and about the client on the other side of it

• You're comfortable when the problems are consequential and rarely perfectly clean

• You're collaborative and generous by default: you share what you know, invest in the people around you, and help the whole team get better

• You're curious about the "why" behind the systems, not just the code

🌸 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.

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.