Senior Manager, Cross-Border Tax & Customs

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.

Were using AI to solve cross-border complexity. Weve already launched an HS code and customs duty calculator in beta. Were 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. Youll own the tax and compliance layer for cross-border e-commerce: customs duties import VAT HS classification landed cost and duty recovery.

Youll report to our Head of Tax and work across the business. One day youre building HS classification frameworks for a merchant catalog. The next youre advising on DDP vs DAP economics. The day after youre 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 dont bleed margin or surprise customers.

Were building AI-powered tools to solve these problems at scale. Youll help shape how we train models for HS classification validate duty calculations and automate compliance workflows. Youll combine deep tax knowledge with a willingness to build systems that didnt exist before.

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

What Youll Get

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

Youll 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 Youll 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 doesnt 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 merchants 10000 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

Build a duty drawback process for high-return categories like apparel and footwear

Assess import VAT obligations for expansion into three new markets

Work with engineering to build duty estimation thats accurate within 2% at checkout

Debug why shipments are getting stuck at German customs and fix the root cause

Improve our AI-powered HS classification tool by building training data and validation frameworks

What Were Looking For

Ideal background:

Cross-border e-commerce platforms (Global-e eShopWorld Flow Commerce Passport Zonos)

Logistics with customs exposure (Flexport DHL Trade UPS Customs Brokerage)

Retailers running cross-border physical goods at scale (ASOS Farfetch Zalando)

Big 4 or tax advisory with indirect tax and customs focus Landed cost or duty calculation platforms (Avalara Cross-Border Zonos)

Signals we care about

You can explain the difference between customs duties tariffs and import VAT without hesitation

You know why HS classification is hard and how to approach it at scale

You understand when DDP beats DAP on unit economics

Youve dealt with IOSS UK low-value or other import simplification schemes

Youve handled duty drawback or import VAT recovery on returns

Youre comfortable with ambiguity. Startups dont come with playbooks

You want to build systems not just advise on policy Bias for action. You solve problems you dont just flag risks

Bonus:

Familiarity with US sales tax (state nexus Wayfair)

Experience with VAT/GST on digital goods

Exposure to MoR models

Interest in AI and automation for tax compliance

What this role is not:

Not pure advisory without operational depth

Not someone who only reviews and flags risks

Not someone who needs defined processes to be effective

Why This Role Is Different

Most tax roles at startups focus on VAT compliance for digital goods. This role is different.

Youll own the physical goods tax layer for a company building global commerce infrastructure. Customs duties import VAT landed cost HS classification duty recovery. The hard stuff that most platforms avoid or outsource.

If you want to go deep on cross-border physical goods and build the systems that make it work this is where you do it.

Outpost Team

Our team were leaders at Revolut Airwallex Adyen and Wayflyer and were backed by top-tier investors who have built or backed some of the worlds leading fintechs.

What We Offer

Equity and salary in a well-funded startup

Ability to own your work and move fast

Direct access to the founding team

A global mission with real impact

Low politics high output

Chance to grow into a senior leadership role

A culture of builders not talkers

Working Style

We work together in person in London or Amsterdam. We believe the hardest problems are solved in the room.

Learn More

Outpost Culture: Outpost founder: is where the hard problems are. If you want to build the infrastructure for global physical goods commerce wed love to hear from you.

Required Experience:

Senior Manager