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Clear Street Logo Clear Street · Finance

Associate Director, Settlements

Canada, Toronto · Job Posted March 10, 2026
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Job Description

The Associate Director, Settlements will own Canadian securities settlement operations for the firm, with primary responsibility for equities and related cash movements settling through CDS/CDSX. This role combines hands-on operational expertise with leadership, risk ownership, and process design. Initially, the role will focus on day-to-day settlement execution, fail management, reconciliations, and control oversight. Over time, responsibilities will expand to support new products, increased volumes, regulatory change, and ongoing automation efforts. This is a senior role requiring strong judgment, comfort operating close to risk, and the ability to scale processes without introducing fragility.

Job Responsibility

  • Settlement of Canadian equity trades through CDS/CDSX, including DVP/RVP processing
  • Daily monitoring and resolution of settlement fails, including buy-ins, close-outs, and escalation of aged or high-risk items
  • Oversight of cash, position, and suspense account reconciliations related to Canadian settlement activity
  • Direct interaction with CDS as a participant, including inventory movements, entitlements, and settlement-related Corporate Action impact
  • Management of settlement flows related to securities lending and borrowing, where applicable
  • Investigation and resolution of settlement breaks across internal books and records
  • Ownership and execution of daily, monthly, and quarterly operational controls, including documentation and evidence retention
  • Partnership with Trading, Finance, Compliance, and Technology on settlement impacts of new products, changes, or incidents
  • Design and implementation of automation, reporting, and exception management tooling to reduce manual touchpoints and operational risk
  • Hiring, managing, and developing settlement staff
  • Driving continuous improvement in controls, processes, and transparency as the platform scales

Requirements

  • 7+ years of experience in settlement operations, with direct CDS/CDSX experience required
  • Prior experience at a Canadian broker-dealer or major Canadian financial institution
  • Strong understanding of Canadian settlement conventions and best practices
  • Demonstrated ownership of operational risk and controls, not just execution
  • Experience managing settlement fails, reconciliations, and time-sensitive exceptions
  • Proven people management experience, including hiring, coaching, and performance management
  • Strong analytical skills and comfort working with data to drive decisions and automation
  • Ability to operate with a high degree of autonomy in a fast-moving environment
  • Clear, direct communicator with strong judgment under pressure
  • Understanding of CIRO rules and guidance as it relates to settlements
  • Understanding of CDS participant requirements and best practices
  • Canadian Securities (CSC) course certification

Nice to have

  • Partners, Directors, and Senior Officers Course (PDO) certification
  • Knowledge of DTC settlement systems and processes
  • Knowledge of Global Custody structure and workflows

What we offer

  • Competitive compensation packages
  • Company equity
  • 401k matching
  • Gender neutral parental leave
  • Full medical, dental and vision insurance
  • Lunch stipends
  • Fully stocked kitchens
  • Happy hours
  • A great location
  • Amazing views
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