Senior Brokerage Operations Associate (Canada)
Remote - CanadaWho 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 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: transparent 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)Custody & asset servicing (segregation, security movements, corporate actions, cash)Books & records, reconciliations, exception management, and operational controlsRegistered accounts & tax ops: TFSA, RRSP, RESP and related wrappers;
tax lots / cost basis;
withholding;
local reporting partners need to stay compliantDay-2 production ops: runbooks, escalations, vendor/custody interfaces, BCP/DR operational playbooksHow 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 againstAutomation-first by default
— redesign high-volume / high-risk / high-friction work for straight-through processing, rules, exception queues, and measurable SLAs, instead of spreadsheet heroicsAI-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 itGo-live and beyond
— Readiness for ACCC launch and early production;




continuous improvement after go-liveRaise the bar without managing a team
— Coach partners through expertise, crisp documentation, and decision logs;
leave systems others can runHow we'll measure success:
Launch readiness gates met with documented controls, SOPs, RACI, and runbooks Product / Eng / Ops can execute againstSTP, exception, and reconciliation aging targets defined and trending the right way post go-liveRegistered-account and tax workflows ready when partners launch, rather than added laterSpecs and decision logs that remove re-discovery for Product and EngineeringSystems and playbooks others can run after you, so knowledge sticks in the org and not only in one person's headWho 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 CanadaFluent in the plumbing: clearing / settlement, custody, CDS / CDSX (or equivalent), fails, corp actions, tax, cash / securities ops, account servicing, introducing / carrying arrangementsDemonstrated depth in at least two of: clearing / settlement;
custody & asset servicing;
books & records / reconciliations;
registered accounts & taxRegulatory-literate (CIRO / provincial securities / CSA context). You design operable controls, and you are not the UDP or compliance sign-off ownerBuilder: you've redesigned and shipped process + tooling changes that stuck, not only run BAUPractical with automation and AI (workflow automation, rules engines, RPA, or AI-assisted ops). You know where AI helps and where controls must stay deterministicExceptional written communication: SOPs, RACI, decision logs, and requirements that cross-functional teams can ship againstWho you might be (Nice-to-haves):
API-first or broker-as-a-service / correspondent platformsUS and Canada dual-entity operationsDeep CDS / CDSX or Canadian market-infrastructure experienceRegistered-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 prototypingHow We Take Care of You:
Competitive Salary & Stock OptionsNew Hire Home-Office Setup: One-time USD $500Monthly Stipend: USD $150 per month via a Brex CardAlpaca is proud to be an equal opportunity workplace dedicated to pursuing and hiring a diverse workforce.We use Greenhouse's AI-powered Talent Matching tool to compare your application against our job requirements.
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📌 Senior Brokerage Operations Associate (Canada) (Winnipeg)
🏢 Alpaca
📍 Winnipeg