Head of Operations

🌍 About OutpostGlobal expansion is broken. Without a local entity, conversion rates fall, costs rise, and compliance gets messy. Outpost fixes it.Selling internationally is a maze of tax, payments, and operational friction.

Most brands avoid it or expand slowly and expensively.Outpost is your modular back office for global commerce.Pick only what you need - tax, payments, treasury, or operations - and unlock new markets without the overhead. Sometimes we act as Merchant of Record, taking on tax and compliance risk. Other times, we give you the tools to do it yourself.We operate across 58+ tax jurisdictions for digital and physical goods.

That means we own the full stack - payments, tax, compliance, treasury, and merchant experience.Sell anything, anywhere. Without compromise.🧠 The RoleWe're looking for our Head of Operations: the person who owns how Outpost actually runs.Today, operations at Outpost is a set of processes held together by a small group of very good people. Merchant onboarding, KYC/KYB, market launches, tax registrations, payouts, treasury approvals, chargebacks, merchant support - it all works, but it works because people push it.

Your job is to turn that into a machine.This is a hands-on leadership role, not a management layer. You'll own the operational stack end to end: onboarding and activation, merchant operations, payments and treasury ops, compliance monitoring, and new market launches. You'll design the processes, build the tooling

Requirements

with engineering, write the playbooks, and then run them yourself until they're good enough to hand over.You'll hire and grow a small team behind you, but for the first stretch you are the team. If your instinct when something breaks is to open the dashboard and fix it rather than schedule a meeting about it, you'll do well here.You'll work directly with the CEO and founding team, and you'll have a real say in what Outpost builds - operations is the sharpest source of product signal we have.🧗 What You'll GetYes, the work is intense. But in return, you'll get scope and exposure most people wait 10 - 20 years to access.You'll own a core function of a company solving one of the hardest problems in global commerce, work with senior stakeholders across PSPs, banks, tax authorities and merchants, and build a team from scratch.

We won't handhold, but we'll coach you hard.🧩 What You'll DoOwn the operational stackOwn merchant onboarding end to end: applications, KYC/KYB, risk review, activation, time-to-liveRun merchant operations day to day - support escalations, payouts, settlements, disputesOwn treasury operations: proceeds requests, money movement, reserves, reconciliationMonitor merchant risk and compliance thresholds (chargebacks, fraud, refunds) and act before they become lossesOwn payment operations alongside engineering: auth rates, routing, decline recovery, chargeback and fraud strategyBuild the system, not just the outputTurn manual processes into documented, repeatable, measurable playbooksDefine the operational metrics that matter and build the reporting so the company can see themWork with engineering to spec and prioritise internal tooling - you are the customer for our internal ops platformKill work: automate, template, or delete anything that doesn't need a humanMake Outpost able to double merchant volume without doubling ops headcountLaunch and scaleLaunch new markets with full legal, tax, payments, and operational setupOnboard new PSPs, banking partners, and local acquiring in new geographiesBuild the operational side of new products and merchant segments before they go liveFeed market and merchant reality back into the product roadmapLeadHire, onboard, and grow a small operations teamSet standards: what good looks like, how fast we respond, what we never get wrongBe the operational voice in company planning - what we can support, when, and at what cost💥 Example ProjectsRedesign merchant onboarding to cut time-to-live by 50% without weakening KYBBuild the operational launch playbook for three new markets and run the first one yourselfDebug delays in payouts and fix them across engineering, ops, compliance, and PSPsDesign reserve and settlement logic for a new merchant segment and implement itBuild the ops metrics dashboard: onboarding funnel, time-to-live, ticket volume, payout SLA, chargeback rateCut chargeback rate through better fraud tooling and merchant policySpec the next version of our internal ops tooling with engineering and ship itWrite the merchant VAT compliance playbook across EU markets with the tax teamHire and onboard the first two operations analysts and get them productive in 30 days🧱

What We're Looking For

Ideal background:6 - 10 years in operations at high-growth fintech, payments, or e-commerce infrastructure (Revolut, Stripe, Adyen, Wise, Mollie, Airwallex, Checkout.com, or similar)Has owned a function or a large slice of one - onboarding, merchant ops, payment ops, or risk ops - not just executed within itExperience building processes from zero, not inheriting themBonus: MoR platforms (Global-e, Digital River, Paddle), cross-border tax exposure, or PSP/acquirer operationsComfortable with data - SQL, spreadsheets, dashboards. You measure before you decideSignals we care about:Ridiculous bias for action - you solve, not observeSystems thinker who still does the work - you fix the ticket and then remove the reason it existedAnalytically strong - you can quantify a process, not just describe itStrong EQ - you know how to read a room, a customer, or a blockerExceptionally hard working - you see work as a core part of your purposeFluent in ambiguity and chaos - startups are not neat, this will be hardCurious and resourceful - you can figure anything outComfortable getting hands dirty - your default mode is to do, not delegateClear, quantified achievements on your CV (not vague descriptions)What this role is not:Not a people-management role where you run a team that does the workNot a process-maintenance role - nothing here is finishedNot a single-function specialist who wants to stay in payments, or compliance, or supportNot someone who needs defined processes and hierarchy to be effective🚀 Why This Role Is DifferentThis isn't about maintaining processes - it's about building the operating system of Outpost from the ground up. You won't just be in the room, you'll be writing the agenda.Operations at an MoR is not a back-office function.

It is the product. How fast merchants go live, whether money arrives on time, whether we catch risk before it costs us - that's what customers buy and where our margin lives. You'll own it.We expect whoever is in this role to grow rapidly, and we'll back you every step of the way.🦾 Outpost TeamOur team were leaders at Revolut, Airwallex, Adyen and Wayflyer - and we're backed by top-tier investors who have built or backed some of the world's leading fintechs.🧾 What We OfferEquity and salary in a well-funded startupAbility to own your work and move fastWorld-class training from operators who've scaled globallyA global mission with real impactLow politics, high outputChance to grow into a senior leadership roleA culture of builders, not talkers🧭 Working StyleWe work together in person in London 5 days a week.

We believe the hardest problems are solved in the room.🌎 Reach OutLearn moreOutpost CultureOutpost founderOutpost is where the hard problems are. If you want to help build the engine behind global trade, we'd love to hear from you.Find Jobs in United Kingdom on Arbeitnow