Head of Operations

About Outpost

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.

The Role

We'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 Get

Yes, 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 Do

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

Build the system, not just the output

• 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

• Kill work: automate, template, or delete anything that doesn't need a human

• Make Outpost able to double merchant volume without doubling ops headcount

Launch and scale

• 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

Lead

• 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

Example Projects

• Redesign merchant onboarding to cut time-to-live by 50% without weakening KYB

• Build the operational launch playbook for three new markets and run the first one yourself

• Debug delays in payouts and fix them across engineering, ops, compliance, and PSPs

• Design reserve and settlement logic for a new merchant segment and implement it

• Build the ops metrics dashboard: onboarding funnel, time-to-live, ticket volume, payout SLA, chargeback rate

• Cut chargeback rate through better fraud tooling and merchant policy

• Spec the next version of our internal ops tooling with engineering and ship it

• Write the merchant VAT compliance playbook across EU markets with the tax team

• Hire 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 it

• Experience building processes from zero, not inheriting them

• Bonus: MoR platforms (Global-e, Digital River, Paddle), cross-border tax exposure, or PSP/acquirer operations

• Comfortable with data — SQL, spreadsheets, dashboards. You measure before you decide

Signals we care about:

• 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)

What this role is not:

• Not a people-management role where you run a team that does the work

• Not a process-maintenance role — nothing here is finished

• Not a single-function specialist who wants to stay in payments, or compliance, or support

• Not someone who needs defined processes and hierarchy to be effective

Why This Role Is Different

This 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 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

View email address on jobs.ashbyhq.com

Learn more

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.