Opportunities from Outpostnow (ashby)

PAYMENT OPERATIONS LEAD Global expansion is broken. Without a local company, 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 become liable for a merchant's taxes. Sometimes we become the legal reseller in each market and carry the payments, tax and compliance risk. Other times, we give you the tools to do it yourself. We go live wherever a merchant needs to sell next, 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 ROLE We're looking for a Payment Operations hire to own the part of Outpost where the money actually moves. When we become the legal reseller in a market, we take the payment. Every merchant we onboard gets its own merchant ID and its own merchant category code, never pooled into one shared code, which is exactly why our approval rates beat the alternatives. Keeping that true across every market, every processor and every merchant is the job. This is a quantitative role in an operational seat. You'll live in the transaction data: why authorisation rates differ by market, issuer, card type and hour of day, what a routing change is actually worth, where a 40 basis point cost difference is hiding, which decline codes are recoverable and which are noise. Then you'll act on it, with processors, with engineering, and with merchants. You won't be siloed. Payments at Outpost touches pricing, treasury, tax and the product roadmap, and you'll be pulled into all of it. But your edge is the numbers, and we want someone whose first instinct on any problem is to pull the data and model it. You'll work directly with the founding team and with engineering, who will build what you spec. 🧗 WHAT YOU'LL GET Yes, the work is intense. But in return you'll get scope and exposure most people wait 10 to 20 years to access. You'll own economics that decide whether the company is profitable, negotiate with processors and banks as a principal rather than a customer, and get to see the full machinery of cross-border payments from the inside. We won't handhold, but we'll coach you hard. 🧩 WHAT YOU'LL DO Build the system

• Run payment operations agentically. Build agentic system that monitor approval rates, triage declines, assemble dispute evidence, chase reconciliation breaks and draft the processor follow-up, so humans only touch the exceptions. You'll design the workflows, set the guardrails, and audit what the agents produce
• Write the playbooks: new processor onboarding, new market launch, incident response, dispute handling
• Onboard new processors, banking partners and local acquiring as we launch new markets Own payments performance
• Own approval rates by market, processor, issuer, card type and merchant, and know why each one moves
• Build and run routing logic. Decide what goes where, prove the uplift, and iterate
• Run decline recovery: retry logic, network tokens, account updater, 3DS strategy and exemption handling
• Run chargeback operations and fraud strategy. Set thresholds, represent disputes, keep merchants inside scheme limits
• Own the payment incident path. When authorisations drop in one market at, you're the one who spots it and fixes it Own the economics
• Build full visibility into cost per transaction: scheme fees, interchange, processor margin, FX, and where each one leaks
• Own processor relationships day to day. Performance reviews, pricing negotiations, new partner evaluation
• Model the trade-off between approval rate and cost by market, and make the call
• Feed real payment economics into how we price merchants Own the money movement
• Settlement, reconciliation and payouts. Every penny accounted for, every break chased down
• Reserve logic and settlement timing by merchant segment and risk profile
• Work with treasury on funding, FX exposure and cash timing across our local companies 💥 EXAMPLE PROJECTS
• Take a market from a 66% approval rate to 90% or better, and prove exactly which changes did it
• Build the routing framework that optimises approval rate against cost, market by market
• Renegotiate processor pricing using our own volume and performance data
• Build the cost-per-transaction model across every processor and market, and find the basis points nobody is watching
• Debug delays in settlement and fix them across engineering, operations and the processor
• Design reserve and settlement logic for a new merchant segment and implement it
• Cut chargeback rate through better fraud tooling and merchant policy
• Evaluate and onboard a new processor for local acquiring in Latin America or Asia
• Build the payments monitoring layer so anomalies find us, not the other way round 🧱 WHAT WE'RE LOOKING FOR Ideal background:
• A STEM or quantitative degree is strongly preferred - mathematics, physics, engineering, computer science, statistics, econometrics or similar.
• 3 to 7+ years in payment operations, payment analytics, or a data or analytics role that moved into payments, at a processor, acquirer, or high-volume fintech (Adyen, Stripe, Checkout.com http://Checkout.com, Nuvei, Worldpay, Revolut, Wise, Dojo, Airwallex or similar)
• Strong analytical skills — advanced Excel or Sheets, experience with BI tools, and the ability to build models and run analyses independently without waiting for a data team.
• Bonus: experience at platforms that act as the legal reseller (Global-e, Digital River, Paddle), local acquiring outside Europe and the US, interchange and scheme fee economics, or a background in data science or quantitative consulting before payments Signals we care about:
• Ridiculous bias for action. You solve, you don't observe
• Analytically strong and commercially sharp. You quantify the opportunity before you argue for it
• Systems thinker who still does the work. You fix the transaction, then remove the reason it broke
• Strong EQ. Processors, banks and merchants all need managing, often at the same time
• Exceptionally hard working. You see work as a core part of your purpose
• Fluent in ambiguity and chaos. Startups are not neat, this will be hard
• Curious and resourceful. You can figure anything out
• Clear, quantified achievements on your CV, not vague descriptions What this role is not:
• Not a payments strategy role without operational depth. You'll be in the dashboards daily
• Not a pure analytics role. The analysis is the start, the change is the job
• Not a narrow specialist seat. Payments here touches pricing, treasury, tax and product
• Not for someone who needs defined processes and hierarchy to be effective 🚀 WHY THIS ROLE IS DIFFERENT Most companies treat payments as a cost centre someone else manages. Here it is the product and the margin at the same time. We take legal responsibility for our merchants' payments. That means a point of approval rate is real revenue for them and real evidence for us, and a basis point of cost is real profit. Very few people get to own that surface this early, with this much data and this little bureaucracy in the way. We expect whoever is in this role to grow rapidly, and we'll back you every step of the way. 🦾 OUTPOST TEAM Our 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 OFFER
• Equity and salary in a well-funded startup
• Ability to own your work and move fast
• World-class training from operators who've scaled globally
• A global mission with real impact
• Low politics, high output
• Chance to grow into a senior leadership role
• A culture of builders, not talkers 🧭 WORKING STYLE We work together in person in London 5 days a week. We believe the hardest problems are solved in the room. 🌎 REACH OUT emile@outpostnow.com Learn more

1. Outpost Culture https://app.notion.com/p/Outpost-Culture-18aa047bb9af800b8f6ff5f5c83174b1?pvs=21
2. Outpost founder http://www.littlegoatlabs.com/ Outpost is where the hard problems are. If you want to help build the engine behind global trade, we'd love to hear from you.