Strategy & 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.

Sell anything, anywhere. Without compromise.

🧠 The Role

At Outpost, Operations means problem-solving at scale. We tackle the company's toughest challenges with speed, precision, and creativity. We design systems that unlock efficiency and power global growth.

We're looking for a Strategy & Operations generalist to help shape how we continue to expand and operate. You'll work on high-impact initiatives across the business: product, finance, GTM, pricing, onboarding, and partnerships. You'll use insight to solve challenges, scale processes, and deliver better outcomes for our merchants.

This is a generalist role. You'll value breadth over depth. One week you're building a financial model for a new market, the next you're scoping a product feature with engineering, the week after you're closing a merchant deal. If you want to stay in one lane, this isn't for you.

You'll work directly with the CEO and founding team. If you're hungry, you'll gain experience most people wait 10-20 years to access.

🧩 What You'll Do

Product

• Act as the eyes and ears of the company, feeding market and merchant insight back into the product roadmap

• Scope and prioritise features based on merchant pain and commercial opportunity

• Work with engineering to ship improvements fast

• Track product performance and competitive positioning

Operations & GTM

• Build and optimise scalable processes across onboarding, compliance, and merchant operations

• Launch new markets with full legal, tax, payments, and operational setup

• Close deals: talk to customers, unblock objections, get contracts signed

• Create playbooks and documentation that help us scale without adding headcount

Finance & Strategy

• Model unit economics for new markets, products, and pricing structures

• Build and maintain financial models for investor updates, KPI tracking, and market planning

• Support fundraising, board materials, and investor relations

• Define which projects the team should prioritise and set timelines to reach goals

💥 Example Projects

• Build a financial model for Mexico market entry including entity costs, tax rates, and payback period

• Scope the requirements for a new onboarding flow and work with engineering to ship it

• Design and implement a new merchant onboarding flow that reduces time-to-live by 50%

• Create the playbook for merchant VAT compliance across EU markets

• Track and analyse competitive positioning against other MoR platforms

• Model reserve and settlement logic for a new merchant segment

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

🧱 What We're Looking For

Ideal background:

• High-growth fintech or tech company (Revolut, Stripe, Wise, Mollie, or similar)

• Strategy consulting, investment banking, or PE/VC with a move into operating roles

• Product, strategy, or business operations roles (not pure support or maintenance)

• STEM degree preferred but not required if you can demonstrate analytical horsepower

Signals we care about:

• Ridiculous bias for action: you solve, not observe

• Analytically strong: comfortable building models, running SQL, making data-driven decisions

• 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 pure strategy or advisory role where you recommend but don't execute

• Not a single-function specialist who wants to stay in one area

• 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.

You'll have exposure to every part of the business: product, finance, GTM, operations. You'll work directly with the founding team. You'll shape the future of a company solving one of the hardest and most valuable problems in global commerce.

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. We believe the hardest problems are solved in the room.

🌎 Reach Out

[email protected]

Learn more

1. Outpost Culture

2. Outpost founder

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.