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Outpost Technologies

AI-powered cross-border commerce MoR/ToR platform

Junior Strategy & Operations

Full-Time
No salary listed
Entry
Bachelor's
London, UK
In Person
Business & StrategyBusiness Operations

About the job

Requirements
  • 0-2 years of experience or exceptional performance straight out of university.
  • Evidence of having built, run, or fixed something real, such as a project, business, system, or analysis.
  • Ability to work comfortably in spreadsheets and curiosity about SQL.
  • Ability to use Claude, scripts, and no-code tools effectively and distinguish reliable output from plausible but incorrect output.
  • Ability to produce precise, checked work suitable for regulatory or merchant-facing contexts.
  • Ability to read customers, rooms, and blockers effectively.
  • Ability to work effectively in ambiguity and startup environments.
  • Evidence of clear, quantified achievements on a curriculum vitae.
  • Ability to provide a link to something built and explain which business area to automate first and how.
Responsibilities
  • Work on initiatives across product, onboarding, market launches, finance, go-to-market, and operations, owning concrete workstreams end to end.
  • Gather merchant and market insights and feed them into the product roadmap.
  • Scope features by gathering pain points, sizing opportunities, and writing initial specifications.
  • Track product performance and competitive positioning using quantitative analysis.
  • Run and improve processes across onboarding, compliance, and merchant operations.
  • Support new market launches by owning and completing legal, tax, payments, and operational checklists.
  • Participate in customer conversations, prepare materials, and follow up to keep deals moving.
  • Write playbooks and documentation that support scaling without additional headcount.
  • Build and maintain models for unit economics, pricing, and market planning.
  • Maintain accurate and current key performance indicator tracking and reporting.
  • Support preparation of investor updates and board materials.
  • Build first-draft financial models for new market entry, including entity costs, tax rates, and payback period.
  • Run merchant onboarding end to end, document friction points, and propose fixes.
  • Convert European Union value-added tax compliance steps into an executable playbook.
  • Track and analyze competitive positioning against other merchant-of-record platforms and maintain the battle card.
  • Debug delayed payouts across engineering, operations, and compliance, and document the fix.
  • Automate manual weekly processes using scripts or no-code tools.
Desired Qualifications
  • A STEM or quantitative degree is preferred, but not required.
  • Internship or first-role experience in high-growth fintech, technology, consulting, banking, or a startup is desirable.

About the company

Outpost Technologies runs an AI-powered platform for cross-border commerce that acts as the Merchant of Record and Tax of Record for clients. It creates dedicated local entities in each market to handle local payments and acquiring, while Outpost assumes full tax and regulatory liability and compliance. The platform uses an AI engine trained on trade regulations to apply correct tax treatment and customs classification for every transaction, covering VAT, GST, and sales tax filings and audits. The goal is to simplify international trade for merchants by providing end-to-end compliance, payments, and regulatory liability through a single platform.

Company Size

11-50

Company Stage

Series A

Total Funding

$17.5M

Headquarters

London, United Kingdom

Founded

2024

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Simplify's Take

What believers are saying

  • March 2026 funding targets jurisdiction expansion, product development, and headcount growth across Europe and Asia.
  • Outpost’s local-entity payments reportedly improve approval rates about 10% versus cross-border cards.
  • Tariffs, de minimis changes, and OECD reporting rules keep merchant compliance demand rising through 2027.

What critics are saying

  • Paddle, FastSpring, and Global-e already sell similar merchant-of-record compliance bundles in 2026.
  • September 2026 hiring for Head of Sales, RevOps, and Payments signals early commercial buildout.
  • A single VAT audit or licensing challenge in 2027 can cripple Outpost’s liability-heavy model.

What makes Outpost Technologies unique

  • Will Mahon-Heap brought Revolut expansion playbooks and Wayflyer deal experience to Outpost, 2021.
  • March 2026 Ribbit-led $17.5 million Series A backs the MoR and ToR full-liability model.
  • Outpost’s AI monitors 20,000 tax rates, auto-classifies customs, and routes local acquiring.

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Benefits

  • Company Equity

Growth & Insights and Company News

Headcount

6 month growth

-7%

1 year growth

-7%

2 year growth

-7%
Tech Funding News
Mar 10th, 2026
Outpost raises $17.5M to make international selling 'as easy as domestic' amid tariffs — TFN

Outpost raises $17.5M Series A led by Ribbit Capital to simplify cross-border commerce with AI tax compliance and local payment entities. Ex-Revolut exec's platform serves EU, LATAM, NA, Asia merchants

Vestbee
Mar 10th, 2026
Outpost secures $17.5M Series A to power global payments and tax compliance

Outpost secures $17.5M Series A to power global payments and tax compliance. London- and New York-based startup Outpost, which develops software to help businesses manage payments, taxes and compliance when selling across borders, has raised $17.5 million in a Series A funding round led by Ribbit Capital, as Vestbee was told. * Launched in 2023 by Will Mahon-Heap, Outpost develops software that handles payments, tax compliance, and legal liability for companies selling digital products and services across borders. The platform acts as a "merchant of record," meaning it processes payments through its own local entities in different countries while taking responsibility for taxes such as VAT, GST, and sales tax. * According to the startup, its system monitors more than 20,000 indirect tax jurisdictions and applies the correct tax treatment and customs classification automatically for each transaction. The company says routing payments through local acquiring infrastructure can increase approval rates by about 10% and reduce processing costs compared with traditional cross-border card transactions. * Outpost reports that its tools are already used by merchants operating across Europe, North America, Latin America, and Asia, including subscription platforms, software companies, and cross-border e-commerce businesses that accept payments in dozens of markets and more than 100 countries. Details of the deal. * The Series A round was led by Ribbit Capital, with support from existing investor Better Tomorrow Ventures and angel investors including executives from Revolut, Uber, Affirm, Airwallex, and Checkout.com. "Outpost's rapid growth is a testament to the world-class team they have assembled and their ability to absolve merchants of operational complexity. While other players are building incremental tools, Outpost has attacked the problem with a full stack model that other providers simply can't match. We are incredibly excited to continue supporting Outpost as they coordinate the economic, administrative and regulatory rails that redefine global trade," claims Nihar Bobba, Partner at Better Tomorrow Ventures. * Outpost plans to use the new funding to accelerate product development, expand its coverage into more global jurisdictions, and increase headcount as demand for cross-border commerce infrastructure grows. The company aims to further develop its AI-powered platform while scaling operations to support more merchants selling across Europe, North America, Latin America, and Asia.