About Loop

Loop is a fast-growing FinTech high growth startup that enables businesses to seamlessly manage money around the world so our clients can access more markets, accelerate their growth and simplify their operations with the only truly cross-border banking platform. Loop is enabling the next generation of businesses to thrive around the world and we are looking for ambitious people to join our mission.

About The Role

Hi, I'm Yan, Head of Engineering at Loop, and I'm hiring our first Payment Operations Lead to own, scale, and modernize the core engine that moves our customers' money.

This is a senior, hands-on role. You won't be sitting on top of a team handing out work — you'll be the person who knows our settlement flows better than anyone, who can pull the SQL, reconcile the variance, get on the phone with the bank, and write the SOP. You'll set the strategy and execute it, and over time you'll build the team underneath you.

This role is an onsite position at our downtown Toronto office (Bay and Bloor).

Where You Come In

Loop moves money across borders, currencies, banking partners, and card networks every day. As we scale, payment operations becomes one of the most important and least forgiving functions in the company. A reconciliation that drifts, a settlement that fails silently, a chargeback queue that grows unattended: these are the things that erode customer trust and burn cash.

You'll own that function end-to-end. You'll be accountable for making sure every dollar of customer money moves accurately, on time, and under controls we'd be proud to show an auditor or a regulator. And you'll be the person who turns today's manual workflows into the automated, observable, well-instrumented operation Loop needs at 10x our current volume.

You'll report directly to me (Yan, Head of Engineering) and work shoulder-to-shoulder with Dave (Head of Finance), our Product and Engineering teams, Customer Support, and our banking and processor partners.

What You'll Be Doing

Own Payment Operations & Money Movement

• Own daily execution of payment settlements across internal accounts, banking partners, network providers, and customers — the buck stops with you.
• Investigate and resolve payment exceptions, failures, and returns yourself; build the playbooks and tooling so the next person can resolve them faster.
• Forecast and monitor liquidity and projected settlement volumes; make sure we always have the right funds in the right account at the right time.
• Own the chargeback process end-to-end: dispute handling, ledger impact, and root-cause analysis (customer-facing communication stays with Customer Support).
• Be the primary operational point of contact for banking partners and payment processors — the person they call, and the person who calls them.
• Set the bar for what "timely, accurate, and compliant customer money movement" means at Loop, and hold the org to it.

Financial Reconciliation, Reporting & Controls

• Run daily three-way reconciliations between internal ledgers, processor reports, and bank statements. Find variances. Resolve them. Document the fix.
• Design and operate the internal controls that safeguard company and customer funds — and tighten them as we grow.
• Produce the weekly and monthly operational reports, KPIs, and dashboards the executive team relies on to understand the health of the business.
• Partner with Finance on month-end close: transaction fee journals, operational balance reconciliations, and anything else that touches the ledger.
• Be the operational point person for audits, bank reviews, and information requests from external stakeholders that are related to our ledgers and money movement.

Strategy, Process & Automation

• Build (and continually rewrite) the SOPs for every payment workflow we run. If it's not written down, it doesn't exist.
• Hunt down manual inefficiencies and partner directly with Engineering, Data, and Product to automate them — write the spec, validate the build, sign off on the rollout.
• Approving the design of new payment features and operational tools; your job is to make sure they actually work in production for real customers, not just on the happy path.
• Set the roadmap for what payment ops at Loop looks like 12 and 24 months out: tooling, automation, controls, team shape. Then go build it.
• Partner cross-functionally to make sure payment ops is a force multiplier for the rest of the business, not a bottleneck.

Desired Qualities, Skills, and Experience

• 7+ years in payment operations, financial operations, or treasury — with meaningful time inside a FinTech, payments company, bank, or processor.
• You've personally run reconciliations and money movement at scale. You can explain three-way recs, settlement timing, and chargeback flows without slides.
• Strong SQL skills. You'll be in the data daily — pulling, joining, validating, building reports. We're not hiring someone to ask a data analyst to run queries.
• You've built or rebuilt a payment ops function before: SOPs, controls, tooling, vendor relationships. You know what good looks like because you've made it.
• Demonstrated ability to work directly with Engineering and Product on automation — translating an operational problem into a spec a dev can build against.
• Comfortable being the most senior person in the room on payment ops topics. You set the standard.
• Strong judgment under ambiguity. We move fast, regulations are real, and the right answer is rarely obvious. You're calm, decisive, and document your reasoning.
• Clear, direct communicator. You can brief the CEO in three sentences and write an SOP a new hire can follow on day one.

Nice to have: experience with cross-border payments, multi-currency settlement, card network operations, or working with Canadian/US banking partners.

What's In It For You

• Be the founding leader of payment ops at one of Canada's fastest-growing FinTechs, building infrastructure used by businesses globally.
• High autonomy, high visibility — you'll work directly with the CEO, Head of Finance, and Head of Engineering on a daily basis.
• A real path to building and leading a team underneath you as Loop scales.
• Make a visible, measurable impact on a core part of the business from week one.

What We Offer

• Salary range: CAD $100,000 – $130,000 base annual, commensurate with experience
• Equity: 0.05% – 0.15%
• 3 weeks vacation
• Group health benefits after probation
• Onsite role in downtown Toronto (Bay and Bloor)
• Kitchen full of snacks and drinks to keep you going throughout the day
• Catered lunch on Fridays (we take recommendations!)

Interview Process

We've kept the interview process deliberately short and weighted toward real work — because for a role this senior and this hands-on, we'd rather see you in action than put you through five rounds of conversation.

• 30-minute virtual meeting with Mandy, People and Business Operations Specialist
• 30-minute virtual meeting with Yan, Head of Engineering
• Two-day paid in-office trial. You'll spend two days with us in the Toronto office reviewing what we have today — our flows, tooling, reconciliations, SOPs, open issues — and come back with a written list of what you'd improve, in what order, and why. This is the centerpiece of our process: it tells us how you think, and it tells you whether this is the team and the problem you want to spend the next few years on.
• Two 30-minute meetings with Sarah, Chief of Staff, and Cato, CEO and Co-Founder, during the in-office trial. 
• Background check and offer.

Our Mission, Vision and Values

• Mission: To help businesses seamlessly manage money around the world so they can access more markets, save money and simplify their operations
• Vision: The future of business is global by default. Loop will be the first business bank that is global by default.
• Values
• • Ownership - We build, raise standards and take full accountability for our results.
  • Speed - We come prepared, make decisions quickly and act without waiting for perfect answers.
  • Respect - We put the customer first, communicate candidly and never compromise on quality.
  • Grit - We finish what we start, run toward challenges and focus on solutions.

How to Apply

To apply for this position, please click “apply” and share your resume, alongside a brief paragraph about yourself and your previous experience. Don't forget to send us your challenge!

Your application will be reviewed by our recruiters and hiring managers; we do not use AI tools for screening or selection.

Loop is committed to creating a diverse culture. We encourage you to apply regardless of who you are or where you came from - what matters is the journey ahead. Put simply, if you’re unsure about your qualifications for this position, we’d still encourage you to apply!