Wealthsimple is a Toronto-based digital money management platform offering investing, trading, crypto, tax, spending and savings products to Canadian consumers.
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 ROLE The mandate is broad and the autonomy is real. You'll have blue sky to research how the org operates, identify the workflows where manual effort, reconciliation breaks, and tooling gaps compound into operational and regulatory risk, and ship the solutions that make those problems go away — sometimes through code, sometimes through workflow redesign, often through AI-augmented automation built in partnership with our agentic workflows team. Read on if you are an engineer who thrives on deep financial-services domain expertise, prefers an operations standup over a JIRA grooming session, and wants to leave your mark on systems that process billions of dollars for millions of Canadians. WHY THIS ROLE EXISTS Wealthsimple's brokerage business is scaling fast. We ship several great investment products yearly, thus expanding our regulatory surface area with every new product. We're investing in embedded engineers because we believe the path to a 10x improvement runs through engineers who work shoulder-to-shoulder with operators, not engineers who build solutions to spec from a backlog. Our 2026 company priority is to cut ops tickets per 1,000 transactions in half. You'll be a key part of getting us there. WHAT YOU'LL DO - Embed with enablement teams — Brokerage Operations, AML/Compliance Supervision, Trade Desk, Treasury, Account Operations, Margin Supervision — to deeply understand how the work gets done and where the friction lives. - Automate high-volume manual workflows end to end, from regulatory reporting (AML STR/LVCTR/EFTR, Form 1/CIRO, DTC asset segregation) to journal entries, reconciliations, collateral monitoring, brokerage liquidations, and complex registered-plan administration. - Advance our risk oversight for leveraged offerings by building automated alerts, managing liquidation processes, and daily reconciliations with external vendors. - Partner with the AI agentic workflows team to make sure what you build is accurate, secure, auditable, and reuses shared components rather than reinventing them. - Exercise judgment on what's the highest impact. You won't be handed a ticket backlog — you'll work with leadership on the Brokerage team, engineering managers, and with the operators themselves to decide what gets built. - Surface the invisible problems. Some of your most valuable output will be insight: pattern recognition across workflows that becomes input to regular R&D planning. WHAT WE'RE LOOKING FOR - Senior software engineer with strong full-stack range and comfort across data pipelines, internal tooling, and AI-augmented workflow automation. - A genuine collaborator with non-engineers — you can sit in an ops standup, ask the right questions, build trust with compliance officers and traders, and translate what you hear into shippable solutions. - Bias for shipping in the weeds. You make judgment calls about what to fix without waiting for a PM to scope it. You close loops yourself. - Comfort with ambiguity. This role rewards engineers who can take a vague "this workflow is painful" and walk out with a concrete diagnosis, a path, and an outcome. - A reuse-first mindset. You coordinate across embedded teams (AML, brokerage tooling, reliability) and integrate with what already exists rather than rebuilding it. - Entrepreneur mindset. You proactively identify what needs doing, take ownership, and drive solutions forward, thriving on autonomy rather than waiting for a predefined problem or plan. - Deep curiosity. You're the person who reads the docs before the meeting, digs into the "why" behind the business requirement, and learns a new domain because you genuinely want to understand how things work — not just what you need to ship. - AI-first mindset. You leverage AI tools to accelerate development, improve code quality, and solve problems more effectively. You have already evolved your workflow through AI and are eager to continue innovating. - Strong written communication. You'll regularly report to the Engineering and Brokerage leadership on what you're learning and where the next 10x opportunity is BONUS POINTS - Experience in fintech, brokerage operations, regulated financial services, or capital markets infrastructure - Familiarity with Oracle/Exadata/EBS, ledger systems, or large-scale internal tooling platforms - A track record of shipping AI-driven workflow automation in regulated environments - Experience leading workstreams that spanned multiple teams or organizations, delivering impact without having direct authority over everyone involved. If this resonates, we'd love to hear from you. Tell us about a manual workflow you've made disappear — what you learned about the people doing the work, what you shipped, and what you'd do differently. 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 employee