Senior Brokerage Operations Associate (Canada)

Who We Are: Alpaca is a US-headquartered, global leader in agent-first brokerage infrastructure for stocks, ETFs, options, crypto, fixed income, 24/5 trading, and more. Amongst our subsidiaries, Alpaca is a licensed financial services company, serving hundreds of financial institutions across 40 countries with our institutional-grade APIs. This includes broker-dealers, investment advisors, wealth managers, hedge funds, and crypto exchanges, totalling over 10 million brokerage accounts. Our global team is a diverse group of experienced engineers, traders, and brokerage professionals who are working to achieve our mission of opening financial services to everyone on the planet. We're deeply committed to open-source contributions and fostering a vibrant community, continuously enhancing our award-winning, developer-friendly API and the robust infrastructure behind it. Alpaca is proudly backed by $400 million in funding from top-tier global investors including Portage Ventures, Spark Capital, Tribe Capital, Social Leverage, Horizons Ventures, Opera Tech Ventures, SBI Group, Derayah Financial, Unbound, Peak XV, Elefund, and Y Combinator. Our Team Members: We're a dynamic team of 400+ globally distributed members who thrive working from our favorite places around the world, with teammates spanning the USA, Canada, Japan, Hungary, Nigeria, Brazil, the UK, and beyond! We're searching for passionate individuals eager to contribute to Alpaca's rapid growth. If you align with our core values—Stay Curious, Have Empathy, and Be Accountable—and are ready to make a significant impact, we encourage you to apply. Your Role: We're seeking a Senior Brokerage Operations Associate (Canada). An experienced individual contributor who has lived dealer, clearing, and custody reality and designs every process as if manual work is temporary. You turn CIRO-aligned operating requirements into scalable, automated, auditable workflows that Product and Engineering can build against. You partner closely with the ACCC President / UDP, Compliance, Product, Engineering, and global Ops. Someone who influences through expertise, crisp documentation, and decision logs, not through a team. Success is measured by launch readiness, STP and control quality, registered-account / tax operability, and systems others can run and not by headcount or heroic spreadsheet ops. What you'll walk into: You won't be starting from zero. You'll be owning live problems: • Getting ready to open: figure out how we open and maintain accounts, process trades, and hold client cash and securities on day one. Build that for ACCC rather than copying a manual process from another firm. • Working with partner brokers: define how a partner firm and ACCC split the work on accounts, trades, and holding client assets, so it still works as volume grows. • After the trade: settlement in Canada (through CDS), trades that fail to settle, and corporate actions such as dividends and splits. Automate the routine cases and keep a clear list of exceptions, instead of running the book in spreadsheets. • Registered accounts and tax: TFSA, RRSP, RESP, and similar accounts. Cover who can open them, contribution rules, what a security cost, tax withheld on dividends and other income, and the reports clients and partners need. • The day after launch: written steps for daily work, checks that our records match the custodian and the market, contacts at vendors and custodians, and a plan if a system or vendor fails. Have these ready before real client volume shows up. • Building Canada: clear handoffs between product, engineering, and operations teams. What you’ll own: • Account lifecycle & client/introducing-broker servicing (onboarding handoffs, KYC/AML ops interfaces, maintenance, transfers) • Trade lifecycle (capture, affirmation, clearing, settlement, fails, breaks) • Custody & asset servicing (segregation, security movements, corporate actions, cash) • Books & records, reconciliations, exception management, and operational controls • Registered accounts & tax ops: TFSA, RRSP, RESP and related wrappers; tax lots / cost basis; withholding; local reporting partners need to stay compliant • Day-2 production ops: runbooks, escalations, vendor/custody interfaces, BCP/DR operational playbooks How you’ll work: • Translate Canadian reality into runnable process — CIRO-aligned dealer/clearing/custody expectations, introducing–carrying dynamics, custody controls, and operational risk into SOPs, RACI, controls, and exception paths Product and Engineering can build against • Automation-first by default — redesign high-volume / high-risk / high-friction work for straight-through processing, rules, exception queues, and measurable SLAs, instead of spreadsheet heroics • AI-first operating lens — Prototype and productize AI-assisted ops (exception triage, recon investigation, SOP Q&A, control-testing support, runbook copilots) with human oversight where risk or regulation requires it • Go-live and beyond — Readiness for ACCC launch and early production; continuous improvement after go-live • Raise the bar without managing a team — Coach partners through expertise, crisp documentation, and decision logs; leave systems others can run How we'll measure success: • Launch readiness gates met with documented controls, SOPs, RACI, and runbooks Product / Eng / Ops can execute against • STP, exception, and reconciliation aging targets defined and trending the right way post go-live • Registered-account and tax workflows ready when partners launch, rather than added later • Specs and decision logs that remove re-discovery for Product and Engineering • Systems and playbooks others can run after you, so knowledge sticks in the org and not only in one person's head Who you are (Must-haves): • 10+ years deep, hands-on Canadian brokerage operations experience at a CIRO dealer, carrying broker, custodian, clearing firm, or brokerage ops function in Canada • Fluent in the plumbing: clearing / settlement, custody, CDS / CDSX (or equivalent), fails, corp actions, tax, cash / securities ops, account servicing, introducing / carrying arrangements • Demonstrated depth in at least two of: clearing / settlement; custody & asset servicing; books & records / reconciliations; registered accounts & tax • Regulatory-literate (CIRO / provincial securities / CSA context). You design operable controls, and you are not the UDP or compliance sign-off owner • Builder: you've redesigned and shipped process + tooling changes that stuck, not only run BAU • Practical with automation and AI (workflow automation, rules engines, RPA, or AI-assisted ops). You know where AI helps and where controls must stay deterministic • Exceptional written communication: SOPs, RACI, decision logs, and requirements that cross-functional teams can ship against Who you might be (Nice-to-haves): • Greenfield Canadian dealer / clearing / custody stand-up • API-first or broker-as-a-service / correspondent platforms • US and Canada dual-entity operations • Deep CDS / CDSX or Canadian market-infrastructure experience • Registered-account or Canadian tax-ops stand-up (TFSA, RRSP, RESP, tax lots, withholding, reporting) • AI-native ops workflow: recurring use of tools like Cursor, Claude, ChatGPT, or custom agents for SOP drafting, exception synthesis, and prototyping How We Take Care of You: • Competitive Salary & Stock Options • Health Benefits • New Hire Home-Office Setup: One-time USD $500 • Monthly Stipend: USD $150 per month via a Brex Card Alpaca is proud to be an equal opportunity workplace dedicated to pursuing and hiring a diverse workforce. Recruitment Privacy Policy