Outpost raises $17.5M Series A to simplify cross-border sales

Outpost lands $17.5M to tackle global selling complexity

Outpost, a fintech startup building infrastructure for cross-border commerce, has raised $17.5 million in a Series A funding round led by Ribbit Capital, as merchants face growing friction from tariffs, shifting regulations and tighter tax enforcement.

Existing investor Better Tomorrow Ventures also participated, following a $3 million seed investment less than a year ago. The round included angel investors with executive backgrounds at Uber, Affirm, Airwallex and Checkout.com.

Building a “full-stack” layer for international trade

Outpost positions its platform as an end-to-end system for handling payments, tax compliance and regulatory obligations across multiple countries. The company says its AI engine is trained on large volumes of trade and regulation data to track changing tax rates and help apply the correct tax treatment and customs classifications.

A key element of its model is operating local entities in different markets, enabling merchants to process transactions locally rather than strictly cross-border—an approach the company says can improve payment approval rates and reduce processing costs.

CEO: Tariffs and fragmentation are making commerce “more hostile”

Will Mahon-Heap, CEO and founder of Outpost and a former leader of Revolut’s international expansion, said merchants increasingly face a choice between expensive consulting and entity setup or taking on significant payments and compliance risk. He said Outpost was built to remove that trade-off by combining local payment processing with full tax liability handling.

Merchant of Record and Tax of Record offerings

The company says customers already use the platform across Europe, North America, Latin America and Asia, spanning subscription platforms, consumer software and cross-border e-commerce. Outpost offers a Merchant of Record product for payments and local compliance through dedicated entities, and a Tax of Record service to manage global VAT, GST and sales tax obligations.

Ribbit Capital partner Nick Shalek called cross-border commerce a multi-trillion-dollar opportunity constrained by fragmented infrastructure, arguing Outpost is building a category-defining platform by absorbing operational and compliance burdens.

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