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Clear Street Logo Clear Street · IT - Administration

Vice President, DevOps

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

The Vice President, Dev Ops will own technical and operational requirements, integrations, escalations, enhancements, and initiatives for our self-clearing business line in Canada supporting Canadian securities operations functions for the firm. This role combines operational experience with technical expertise to effectively collaborate with operations, business, and engineering stakeholders. Initially, the role will focus on documenting, investigating, and escalating all operational and technical needs for Canadian operations, building comprehensive reconciliations, and providing additional back-office operational support when needed. Over time, responsibilities will expand to support new asset classes, business lines, increased volumes, and regulatory change, with a strong focus on scalability, automation, risk management, and efficiency. This role requires an innovative mindset, strong prioritization and decision-making abilities, and comfort operating in a fast-paced environment across many areas.

Job Responsibility

  • Serve as the primary Dev Ops point of contact for Canadian operations needs, partnering closely with Operations, Engineering, and broader business stakeholders
  • Gather requirements, determine impact, identify dependencies / blockers, perform robust testing, and communicate statuses and timelines to stakeholders for all operational enhancements
  • Lead issue escalation efforts end-to-end, including root cause analysis, impact assessment, prioritization, stakeholder updates, and coordination of timely resolutions
  • Design, build, and maintain reconciliations across custody and settlement processes
  • Advise on and support operating procedures, controls, business continuity documentation, and risk mitigation measures
  • Partner with internal teams to enhance operational tooling, workflows, and user experiences
  • Identify and implement automation opportunities across Canadian operations to improve efficiency and reduce manual touchpoints
  • Provide back-office operational support as needed, including support for settlements, asset servicing, tax operations, and exception management during periods of elevated activity or project delivery
  • Monitor key workflows and operational health metrics, proactively identifying risks, control gaps, and opportunities to improve process efficiency
  • Support ongoing business growth by scaling solutions to new asset classes, business lines, and evolving regulatory requirements in Canada
  • Contribute subject matter expertise on Canadian securities operations, controls, and risk management practices
  • Establish strong prioritization frameworks and decision-making processes to manage competing requests effectively in a fast-moving environment

Requirements

  • 8-10 years of experience in the financial or technology industries in an operations, product, data, and/or engineering role
  • Prior experience at a Canadian broker-dealer or major Canadian financial institution
  • Direct CDS/CDSX experience required, infrastructure and integrations experience preferred
  • Basic understanding of Canadian brokerage operations required, subject matter expertise in one or more back-office function strongly preferred
  • Advanced data analysis skills including SQL and experience with data visualization tools (e.g. Tableau, Sigma Computing, Domo, Power BI)
  • Comfort understanding technical stacks and working with both proprietary and external systems and integrations (e.g. operational platforms, clearing/custody systems, data feeds, APIs)
  • High degree of curiosity and continuous improvement mindset, with a demonstrated history of driving scalable, efficient solutions
  • Meticulous organization, project management, and documentation abilities
  • Ability to operate independently and take ownership of ambiguous problems and resolutions in a fast-moving environment while maintaining sound judgment
  • Clear and direct written and verbal communicator with the ability to tailor communications to operational, technical, and/or business audiences
  • Comfortable with Jira and Github

Nice to have

  • Understanding of CDS participant requirements and best practices is a plus
  • Canadian Securities Course (CSC) certification is a plus
  • Understanding of CIRO rules and guidance as it relates to custody functions is a plus
  • Knowledge of DTC systems and processes is a plus
  • Any of the following technical competencies are a plus: AWS S3, MQ, Kubernetes, Linux/Unix, Python, JavaScript, Apache Kafka, Retool, Figma, Postman, workflow automation tools (e.g. Make, Zapier)

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
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