Vice President, DevOps

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Clear Street is hiring a Vice President, Dev Ops to own Canadian self clearing operations, collaborating with Operations, Engineering and business stakeholders in Toronto onsite. The role centers on documenting and escalating operational and technical needs, building reconciliations across custody and settlements, and later expanding to new asset classes, higher volumes and evolving regulatory requirements with a focus on scalability, automation and risk management. Ideal candidates have 8 to 10 years in financial or tech operations, direct CDS/CDSX experience, Canadian broker dealer background, strong data analytics (SQL and Tableau or Power BI), and fluency with Jira and Github, plus a proactive, clear communicator. To apply, tailor your resume to CDS, controls and incident leadership, highlight automation wins, and show collaboration with ops and engineering; indicate willingness for four days in the office.

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 Team:

The Dev Ops team is part of Clear Street's Global Custody department alongside Asset Servicing, Settlements, and Tax Operations. The team's mission is to support Clear Street’s broad business objectives through effective operational risk mitigation, business continuity, controls, procedures, subject matter expertise, and automation that results in a frictionless experience for clients and internal Clear Street users.

The Role:

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.

Key Responsibilities:

• 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 
• 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)

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. #LIHYBRID