Senior Manager, Cross-Border Tax & Customs

🌍 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.

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.

We're using AI to solve cross-border complexity. We've already launched an HS code and customs duty calculator in beta. We're building the infrastructure that makes physical goods commerce as easy as digital.

🧠 The Role

This is a Senior Manager, Cross-Border Tax & Customs role focused on physical goods. You'll own the tax and compliance layer for cross-border e-commerce: customs duties, import VAT, HS classification, landed cost, and duty recovery.

You'll report to our Head of Tax and work across the business. One day you're building HS classification frameworks for a merchant catalog. The next you're advising on DDP vs DAP economics. The day after you're designing import VAT recovery processes for returns.

Physical goods cross-border is one of the hardest problems in e-commerce tax. You need to understand where duties apply, how de minimis thresholds work, when IOSS or UK low-value simplifications kick in, and how to structure landed cost calculations that don't bleed margin or surprise customers.

We're building AI-powered tools to solve these problems at scale. You'll help shape how we train models for HS classification, validate duty calculations, and automate compliance workflows. You'll combine deep tax knowledge with a willingness to build systems that didn't exist before.

This is a hands-on role. You'll do the compliance work and shape the strategy. You'll work with product and engineering to turn complex customs rules into systems. You'll help us launch in new markets and build the infrastructure that lets merchants sell physical goods globally.

🧗 What You'll Get

Yes, the work is intense. But in return, you'll get ownership of one of the most complex and valuable problem spaces in global commerce.

You'll build tax infrastructure from scratch, work directly with the founding team, and shape how Outpost scales physical goods internationally. If you want to go deep on cross-border commerce and build something that matters, this is the role.

🧩 What You'll Do

Customs, Duties & Import VAT

• Own customs duty and import VAT compliance across all markets

• Build and maintain HS classification frameworks for merchant product catalogs

• Advise on de minimis thresholds and when simplifications apply (IOSS, UK low-value)

• Design processes for duty drawback and import VAT recovery on returns

Landed Cost & Checkout

• Build the logic that calculates duties, tariffs, and import taxes at checkout

• Ensure landed cost accuracy so DDP doesn't bleed margin

• Work with engineering to embed duty calculations into checkout flows

DDP/DAP Strategy

• Advise on when to absorb duties (DDP) vs pass through (DAP)

• Build routing logic based on order value, margin, product category, and destination

• Model the economics and help commercial teams price accurately

Compliance & Filings

• Manage import VAT registrations and filings across markets

• Ensure compliance with IOSS, OSS, and equivalent schemes

• Stay ahead of regulatory changes and embed them in systems

• Prepare for audits and manage documentation

New Market Expansion

• Assess duty and import VAT requirements for new market entry

• Advise on entity structure and compliance approach

• Work with external advisors in new jurisdictions

💥 Example Projects

• Build an HS classification framework for a merchant's 10,000 SKU catalog

• Design landed cost calculation logic for UK and EU markets above de minimis

• Create DDP vs DAP routing rules based on margin thresholds by market