Strategy & Operations

OPERATIONS (PAYMENTS)

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.

We operate as Merchant of Record for digital and physical goods across 58+ tax jurisdictions. That means we own the full stack - payments, tax, compliance, and customer experience.

Sell anything, anywhere. Without compromise.

🧠 THE ROLE

This is an Operations role for someone who wants to build like a founder, work like an operator, and happens to have deep payments and acquiring experience.

You'll work directly with the CEO across every part of the business: GTM, pricing, onboarding, treasury, product, and partnerships. You'll run toward the biggest problems, not away from them. Your payments background will be critical - as MoR, we own auth rates, PSP relationships, chargebacks, and payment economics - but you won't be siloed in payments.

This is a "ghostbuster" role. Ghostbusters solve messy problems that don't fit neatly into one function. One week you're negotiating PSP pricing, the next you're debugging merchant onboarding, the week after you're building a new market launch playbook.

Work is a big part of your purpose. You want to build something important, take ownership, and grow faster than anyone around you.

🧗 WHAT YOU'LL GET

Yes, the work is intense. But in return, you'll get training and exposure most people wait 10-20 years to access.

You'll be working on global problems, dealing with senior stakeholders, and owning strategic projects across payments, tax, finance, product, and operations - from day one.

We won't handhold, but we'll coach you hard. If you're hungry, you'll leave this role with a world-class operating skillset.

🧩 WHAT YOU'LL DO

Operate across the business:

- Unblock bottlenecks across GTM, ops, finance, product, and customer onboarding

- Own high-stakes, ambiguous problems - solve and systematise

- Work with product to shape roadmap from the field

- Create playbooks and processes that help us scale

- Talk to customers and partners, and get deals over the line

- Help launch new markets, products, or payment rails

Bring payments depth where it matters:

- Own PSP relationships (Adyen, Nuvei) - negotiate pricing, manage performance, evaluate new partners

- Optimize auth rates, build routing logic, manage decline recovery

- Run chargeback operations and fraud strategy

- Build visibility into payment costs and identify margin opportunities

- Translate payments complexity into product and pricing decisions

💥 EXAMPLE PROJECTS

- Negotiate improved pricing with Adyen based on volume and performance data

- Launch our merchant playbook in 3 new countries

- Build a routing framework that optimizes auth rate vs cost by market

- Debug delays in settlements and fix them across engineering, ops, and PSPs

- Model and implement reserve and settlement logic for a new merchant segment

- Reduce chargeback rate through better fraud tooling and merchant policies

- Identify and pitch a new pricing model based on payment economics

- Evaluate and onboard a new PSP for Latin America local acquiring

🧱 WHAT WE'RE LOOKING FOR

Ideal background:

- Experience at PSPs, acquirers, or payment-adjacent fintechs (Adyen, Stripe, Checkout.com http://Checkout.com, Nuvei, Worldpay, Revolut, Wise)

- Operations roles - not pure product or pure commercial

- Experience with auth optimization, PSP management, chargebacks, or payment ops

- Bonus: MoR platforms (Global-e, Digital River, Paddle) or high-volume e-commerce payments teams

Signals we care about:

- Ridiculous bias for action - you like to solve, not observe

- 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

- You can explain why auth rates differ by market and issuer

- You've negotiated with PSPs or managed PSP relationships operationally

- You understand interchange economics and where margin leaks

What this role is not:

- Not a pure payments specialist role - you'll work across the whole business

- Not payments "strategy" without operational depth

- Not someone who needs defined processes 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.

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