Strategy & 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, 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

Do you have experience in Tax experience?

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. Your payments experience will be a superpower - as MoR, payments is core to our economics. But you'll have exposure to every part of the business, work directly with the founding team and the CEO, and shape the future of a company solving one of the hardest 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.