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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 $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 team

The Derivative Risk Remediation team (DRR) is a small team within Credit Risk Operations (CROPS) responsible for monitoring derivative exposures exceeding $1 billion, which is growing as the business expands its derivative offering. The team identifies and remediates derivative risk across Wealthsimple’s retail book — before exposures become losses. We sit at the intersection of live market risk, regulatory compliance, and operational infrastructure, and we hold ourselves to a high bar on all three. The stakes are real: the decisions this team makes have a direct monetary impact on clients and the firm. If you take operational excellence seriously, want to live the Maker-Owner mindset, and have Naive Ambition, you will feel right at home.

About the role

This role is the operational backbone of the Derivative Risk Remediation team. You’ll own the day-to-day monitoring, remediation, and reconciliation work that keeps our retail derivatives function running — surfacing risk, executing on it, and making sure nothing falls through the cracks. You’ll work closely with the Senior Specialist on cases that require a higher level of judgment, and you’ll be a critical part of a small team where consistent coverage isn’t optional — it’s the whole point.

This isn’t a process-execution role. Exposures and account states vary case by case, and no fixed playbook fits every situation. We need someone with sound judgment, solid derivatives knowledge, the analytical instinct to spot issues before they become obvious, and the technical skills to build and maintain the tools the team relies on. Just as important: this role sits at the intersection of several teams, so we’re looking for someone who stays objective under pressure and works well across functions.

What you’ll do

Monitor dashboards daily to identify derivative risk across the retail book — surfacing concentrations, early assignment events, near-expiry ITM positions, and accounts requiring action, and triaging each case on its merits.
Monitor automations during option liquidations and escape anomalies and failures to Engineering, and ensure changes are implemented to avoid mass failures and stay compliant with policies.
Execute option assignment and exercise workflows, account restrictions, position liquidations, and remediation for early assignment, uncovered positions, corporate actions, and ad hoc trade requests from other teams.
Review derivative scenarios and assess how each affects margin, buying power, and firm exposure — applying working knowledge of dynamic collateral and strategy re-pairing to size and execute remediation actions.
Complete weekly and monthly CIRO audit requirements, documenting findings and controls in JIRA and partnering with the Senior Specialist on any remediation needed.
Build and maintain monitoring tools using SQL, Python, and AI tooling — contributing to dashboards and maintaining automation scripts that surface daily risk views and exposure trackers.
Contribute data, queries, and visualizations that feed team discussions and Risk Committee reporting.
Apply CIRO IDPC margin rules to derivative positions in day-to-day decisions and escape ambiguous or material cases to the Senior Specialist or Team Lead.
Complete ad hoc trades and tasks as assigned by the Senior Specialist or Team Lead.

Skills you bring

1–3 years in derivatives operations, risk, margin operations, or trading support at a CIRO-regulated dealer or equivalent
Working knowledge of retail option strategies (verticals, iron condors, butterflies, covered calls, cash-secured puts, naked options) and their basic risk mechanics, plus a working understanding of futures and options on futures
Solid grasp of option assignment and exercise mechanics, expiry-day operations, corporate actions, and dividend risk; working knowledge of CIRO IDPC margin rules and of dynamic collateral and strategy re-pairing as they apply to remediation decisions
A collaborative mindset — comfortable surfacing risks, contributing to team discussions, and escalating appropriately to the Senior Specialist or leaders
Working-to-intermediate SQL (joins, CTEs, basic JSON parsing), Python for automation scripts and basic API integrations, practical use of AI tooling, and working proficiency with BI platforms and Excel
CSC, CPH, DFOL, and FLC (or equivalent CIRO new proficiency requirements), or CFA Level 1, are required to register as a supervisor

Nice to have

OPSC, IDSC, and CCSE certifications
CFA or FRM candidacy
Experience with futures and futures options
Experience with JIRA, Notion, Slack, Oracle DB, ICE, FactSet, Preset, Apache Superset, or similar tools

Who you are

A reliable problem solver with sound judgment — able to make calculated, low-error decisions under time pressure where the cost of a mistake is immediate and quantifiable, and where the right action varies case by case
Detail-oriented and consistent — you catch things others miss, and you take that responsibility seriously
Technically capable and self-sufficient — you’re comfortable building and maintaining the tools the team depends on without waiting to be asked
Someone who knows when to act and when to escalate — you don’t let ambiguity stall you, but you’re not too proud to bring in the Senior Specialist when a case warrants it
Collaborative by default — you share context early, communicate clearly, and make the team around you more effective

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.

Compensation

CA$69.6K – CA$87K • Offers Equity

Base salary range: For this role, candidates located in Canada can expect a base salary range, described in the posting. Actual compensation is determined based on skills, experience, and role level. Exceptional candidates may be considered above the top of the range, and pay can increase quickly for those who make a big impact in the role.

Total compensation: In addition to base salary, permanent employees receive equity compensation. We use clear job levels and market-based salary bands to ensure compensation is fair and consistent across the company.

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Wealthsimple Technologies