Specialist, Derivatives Risk Remediation

Wealthsimple Technologies

4d • Hybrid

About The Position

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.

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.

Requirements

• 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 Haves

• 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

Responsibilities

• 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 escalate 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 escalate 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.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed