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)