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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.

📆 Application Deadline: Monday Sept 28th, 11:59pm EST

About the team

The Options Clearing team sits within Brokerage Operations, the group responsible for how Wealthsimple executes on behalf of clients across billions of dollars a day. We own the full options life cycle — reconciliations, settlements, exercises, assignments and expirations — and make sure every position we hold matches what it should. It's precise, deadline-driven work, and we take it seriously because clients are trusting us with their money.

About the role

Reporting to the Senior Manager, Options Clearing, you'll own the daily execution of reconciliations, settlements, and expirations across our options book. This work protects client assets directly, so accuracy isn't optional — you're the person who catches a break in the data before it becomes a client-facing problem, and who improves the processes that keep pace as the business grows.

What you'll do

• Own daily reconciliation, settlement, and expiration processing across the options book, catching and resolving breaks before they reach clients

• Act as the team's subject matter expert on OCC and CDCC clearing (including SOLA), covering exercises, assignments, and institutional options transfers

• Partner with the Trade Desk, engineering, and other operations teams to resolve trade and position discrepancies and reduce risk

• Use data — pivot tables, lookups, and SQL — to find the cause of inefficiencies and fix them

• Build and improve the tools and workflows that let the team scale as options volume grows

• Develop processes to increase the efficiency of our back-office operations.

Skills you bring:

• 2+ years handling back-office reconciliations, settlements, or options clearing (OCC/CDCC) at a broker-dealer or registered investment dealer

• Comfortable with large data sets — you can take a few thousand rows of position data, find the breaks, and explain what caused them

• Working knowledge of SQL, or ready to learn it fast — you'll be querying data daily

• Available to support early and late hours on a rotating basis around market events and settlement cycles

• A clear communicator who can work easily with trading, product, and operations teams

Nice to have

• Progress toward or completion of CSC, DFOL, or similar industry courses

• Familiarity with CDS or DTCC settlement

• Familiarity with Claude AI or Claude Code

Who you are

• Naturally curious — when something looks off, you want to know why

• Someone who builds trust with the people around you by being reliable and clear

• Are organized and detail-oriented, with the ability to work accurately against tight, non-negotiable deadlines.

• Willing to escalate early when something needs it, rather than sitting on it

• Genuinely interested in how markets and technology intersect

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.

*Unlimited paid sick days, Wellness Days and the 90 day away program do not apply to certain roles.

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.