Senior Brokerage Operations Associate

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior Brokerage Operations Associate based in Canada. Join a globally distributed fintech team building modern brokerage infrastructure and scalable financial services. In this senior individual-contributor role, you will help establish and optimize Canadian brokerage operations, translating regulatory and market requirements into reliable, automated, and auditable workflows. You’ll oversee critical processes spanning account servicing, trade clearing and settlement, custody, reconciliations, corporate actions, and registered-account taxation. Working closely with Product, Engineering, Compliance, and external brokerage partners, you’ll turn complex operational needs into clear requirements and systems that can scale. You’ll champion automation and AI-assisted operations while maintaining appropriate human oversight and robust regulatory controls. This is an opportunity to shape launch readiness, strengthen operational resilience, and build sustainable processes for a growing Canadian brokerage business without the need to manage a team.

Canadian Brokerage Operations: Design and establish scalable processes for account opening and maintenance, client servicing, transfers, and onboarding handoffs, including operational interfaces with KYC/AML processes. Trade Lifecycle Management: Define and oversee trade capture, affirmation, clearing, settlement, and exception handling, including settlement failures and operational breaks. Clearing and Custody: Develop workflows for Canadian securities clearing and settlement through CDS/CDSX or relevant market infrastructure, covering custody arrangements, client cash and securities, asset segregation, and security movements. Corporate Actions and Asset Servicing: Establish processes for dividends, stock splits, reorganizations, and other corporate actions, with clear controls and exception-management procedures. Books, Records, and Reconciliations: Implement reliable books-and-records processes, reconciliation controls, exception queues, and monitoring mechanisms to maintain accurate records across internal systems, custodians, and market infrastructure. Registered Accounts and Tax Operations: Design operational workflows for Canadian registered accounts, including TFSA, RRSP, and RESP, covering eligibility, contribution rules, tax lots and cost basis, withholding on dividends and other income, and required partner and client reporting. Partner and Vendor Coordination: Define responsibilities and handoffs between the brokerage, introducing and carrying brokers, custodians, service providers, and other external partners to support compliant and scalable operations. Process Documentation and Controls: Translate Canadian regulatory and operational requirements into standard operating procedures (SOPs), responsibility matrices (RACI), control frameworks, decision logs, and exception paths that Product and Engineering teams can implement. Automation and AI Enablement: Identify high-volume, high-risk, or repetitive processes suitable for straight-through processing, rules engines, workflow automation, RPA, and AI-assisted operations. Develop practical solutions for reconciliation investigations, exception triage, SOP support, and control testing while retaining human oversight where required. Launch and Production Readiness: Prepare operational runbooks, daily checks, escalation procedures, vendor contacts, and business continuity and disaster recovery playbooks ahead of launch and early production. Cross-Functional Collaboration: Partner with Product, Engineering, Compliance, and global Operations teams to clarify requirements, resolve operational challenges, and ensure systems reflect real-world Canadian brokerage processes. Continuous Improvement: Track operational performance through straight-through processing (STP), exception volumes, reconciliation aging, service-level targets, and control effectiveness. Improve processes after launch and ensure knowledge is documented and transferable across the organization. Technical Leadership Without Direct Management: Guide stakeholders through subject-matter expertise, clear documentation, practical recommendations, and well-maintained decision records, enabling teams to operate and improve processes independently. Requirements At least 10 years of hands-on Canadian brokerage operations experience within a CIRO-regulated investment dealer, carrying broker, custodian, clearing firm, or comparable Canadian brokerage operations environment. Deep practical knowledge of Canadian brokerage operations, including clearing and settlement, CDS/CDSX, settlement failures, corporate actions, custody, client cash and securities, account servicing, and introducing-versus-carrying broker arrangements. Demonstrated expertise in at least two of the following areas: clearing and settlement; custody and asset servicing; books and records and reconciliations; or registered accounts and tax operations. Strong understanding of the Canadian regulatory environment, including CIRO requirements, provincial securities regulation, and the Canadian Securities Administrators (CSA) context. Ability to design practical operational controls and processes aligned with regulatory expectations, while recognizing the distinction between operational responsibilities and formal compliance or Ultimate Designated Person (UDP) sign-off. A proven track record of redesigning and implementing operational processes, tooling, or workflow improvements that deliver lasting results beyond routine business-as-usual operations. Practical experience with automation technologies such as workflow automation platforms, rules engines, RPA, or AI-assisted operational tools, including the ability to determine where automation is appropriate and where deterministic controls are essential. Excellent written communication skills, with experience producing clear SOPs, RACI matrices, decision logs, functional requirements, and operational documentation that cross-functional teams can execute. Strong analytical and problem-solving skills, sound operational judgment, and the ability to manage complex dependencies across internal teams and external partners. Ability to work independently in a distributed, cross-functional environment and influence outcomes through expertise rather than formal people-management responsibilities. Nice to have: Experience establishing a Canadian dealer, clearing, or custody operation from the ground up. Experience with API-first brokerage infrastructure, broker-as-a-service platforms, or correspondent brokerage models. Experience supporting operations across both US and Canadian legal entities. Deep familiarity with CDS/CDSX and Canadian securities market infrastructure. Experience establishing registered-account and Canadian tax workflows, including TFSA, RRSP, RESP, tax lots, withholding, and reporting. Regular use of AI-native tools such as Cursor, Claude, ChatGPT, or custom AI agents for SOP drafting, exception analysis, operational investigations, and workflow prototyping. Successful completion of the Canadian Securities Course (CSC) is relevant to the role, as highlighted in the application screening questions. Benefits Competitive salary. Stock options. Health benefits. One-time USD $500 home-office setup allowance for new hires. Monthly USD $150 stipend provided through a Brex card. Opportunity to work remotely from Canada as part of a globally distributed team. Opportunity to help build and scale Canadian brokerage operations, with meaningful ownership of processes, automation, and launch readiness.