[Hiring] Senior Brokerage Operations Associate @Alpaca

Role Description

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.

• Turn CIRO-aligned operating requirements into scalable, automated, auditable workflows that Product and Engineering can build against.
• Partner closely with the ACCC President / UDP, Compliance, Product, Engineering, and global Ops.
• Influence 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.

What you'll walk into:

• Getting ready to open: figure out how we open and maintain accounts, process trades, and hold client cash and securities on day one.
• Working with partner brokers: define how a partner firm and ACCC split the work on accounts, trades, and holding client assets.
• After the trade: settlement in Canada (through CDS), trades that fail to settle, and corporate actions such as dividends and splits.
• Registered accounts and tax: TFSA, RRSP, RESP, and similar accounts.
• The day after launch: written steps for daily work, checks that our records match the custodian and the market.
• 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.
• Automation-first by default.
• AI-first operating lens.
• Go-live and beyond.
• Raise the bar without managing a team.

Qualifications

• 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).
• 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).
• Exceptional written communication: SOPs, RACI, decision logs, and requirements that cross-functional teams can ship against.

Requirements

• 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.

Benefits

• 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.

Company Description

Alpaca is a US-headquartered, global leader in agent-first brokerage infrastructure for stocks, ETFs, options, crypto, fixed income, 24/5 trading, and more.

• Licensed financial services company, serving hundreds of financial institutions across 40 countries.
• Global team of experienced engineers, traders, and brokerage professionals.
• Deeply committed to open-source contributions and fostering a vibrant community.
• Proudly backed by $400 million in funding from top-tier global investors.