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About the Role

We're looking for our Head of Operations, the person who owns how Outpost actually runs. This is a hands-on leadership role where you'll own the operational stack end to end, design processes, build tooling requirements, write playbooks, and run them until they're ready to be handed over. You'll work directly with the CEO and founding team, and have a say in what Outpost builds.

Responsibilities

• Own the operational stack
• Own merchant onboarding end to end: applications, KYC/KYB, risk review, activation, time-to-live
• Run merchant operations day to day — support escalations, payouts, settlements, disputes
• Own treasury operations: proceeds requests, money movement, reserves, reconciliation
• Monitor merchant risk and compliance thresholds (chargebacks, fraud, refunds) and act before they become losses
• Own payment operations alongside engineering: auth rates, routing, decline recovery, chargeback and fraud strategy
• Turn manual processes into documented, repeatable, measurable playbooks
• Define the operational metrics that matter and build the reporting so the company can see them
• Work with engineering to spec and prioritise internal tooling — you are the customer for our internal ops platform
• Automate, template, or delete anything that doesn't need a human
• Make Outpost able to double merchant volume without doubling ops headcount
• Launch new markets with full legal, tax, payments, and operational setup
• Onboard new PSPs, banking partners, and local acquiring in new geographies
• Build the operational side of new products and merchant segments before they go live
• Feed market and merchant reality back into the product roadmap
• Hire, onboard, and grow a small operations team
• Set standards: what good looks like, how fast we respond, what we never get wrong
• Be the operational voice in company planning — what we can support, when, and at what cost

Requirements

• 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 it
• Experience building processes from zero, not inheriting them
• Comfortable with data — SQL, spreadsheets, dashboards. You measure before you decide
• Ridiculous bias for action — you solve, not observe
• Systems thinker who still does the work — you fix the ticket and then remove the reason it existed
• Analytically strong — you can quantify a process, not just describe it
• Strong EQ — you know how to read a room, a customer, or a blocker
• 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
• Comfortable getting hands dirty — your default mode is to do, not delegate
• Clear, quantified achievements on your CV (not vague descriptions)

Skills

• SQL
• Spreadsheets
• Dashboards

Location

• London

Work Type

• Onsite
• Full-time

Experience Level

• 6-10 years

Benefits

• 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

About the Company

• Global 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.
• 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.