Senior Software Developer, Brokerage

Portage Ventures GP Inc.; United States; Hybrid; USD 140,000 - 210,000; Full time

Benefits offered by this job

Top-tier health benefits

Long-term group savings with employer

20 vacation days and wellness days

90 days abroad for work outside Canada

Employee resource groups (2SLGBTQ, WS,

Hybrid team with North America

Job summary

Wealthsimple, a leading Canadian fintech, is seeking an experienced Senior Software Engineer to join a fast-growing brokerage operations initiative. You will work across data pipelines, internal tooling, and AI-augmented automation to streamline regulatory reporting, journaling, and reconciliation processes.

You’ll partner with operators and compliance teams to ship reliable, auditable solutions. The role emphasizes ownership, curiosity, and an entrepreneurial mindset within a hybrid North

Qualifications

• 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 — sit in an ops standup, translate needs into shippable solutions.
• Bias for shipping in the weeds; you own what you fix without waiting for a PM to scope it.
• Comfort with ambiguity and a reuse-first mindset across embedded teams.

Responsibilities

• Embed with enablement teams to deeply understand workflows and friction points.
• Automate high-volume manual workflows end to end across regulatory reporting and reconciliations.
• Advance risk oversight for leveraged offerings with automated alerts and daily reconciliations.
• Partner with the AI agentic workflows team to reuse components and ensure security and auditability.
• Exercise judgment on highest impact work with leadership and operators to decide what to build.
• Surface invisible problems with pattern recognition to inform R&D planning.

Skills

Full-stack

Data pipelines

Internal tooling

AI-augmented automation

Collaboration with non-engineers

Tools

Oracle/Exadata/EBS

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 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 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.