Associate Director, Settlements

About Clear Street: 

Clear Street is modernizing the brokerage ecosystem. Founded in 2018, Clear Street is a diversified financial services firm replacing the legacy infrastructure used across capital markets.

We started from scratch by building a completely cloud-native clearing and custody system designed for today’s complex, global market. Clear Street’s proprietary prime brokerage platform adds significant efficiency to the market, while focusing on minimizing risk, redundancy, and cost for clients. Our goal is to create a single source-of-truth platform for every asset class, in every country, and in any currency.

By combining highly-skilled product and engineering talent with seasoned finance professionals, we’re building the essentials to compete in today’s fast-paced markets.

The Role:

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.

The Team:

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

We Offer: 

At Clear Street, we offer competitive compensation packages, company equity, 401k matching, gender neutral parental leave, and full medical, dental and vision insurance. Our belief has always been that we are better as a business when we are all together in person. As such, we are requiring employees to be in the office 4 days per week. In-office benefits include lunch stipends, fully stocked kitchens, happy hours, a great location, and amazing views.

Our top priority is our people. We’re continuously investing in a culture that promotes collaboration. We help each other through challenges and celebrate each other's successes. We believe that modern workplaces succeed by virtue of having high-performance workforces that are diverse — in ideas, in cultures, and in experiences. We put in the effort to make such a workplace a daily reality and are proud to be an equal opportunity employer.