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.

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

• 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 that's 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 We're 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

• You've dealt with IOSS, UK low-value, or other import simplification schemes

• You've handled duty drawback or import VAT recovery on returns

• You're comfortable with ambiguity. Startups don't come with playbooks

• You want to build systems, not just advise on policy • Bias for action. You solve problems, you don't 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.

You'll 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 we're backed by top-tier investors who have built or backed some of the world's 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

emile@outpostnow.com

Outpost Culture: https://www.notion.so/Outpost-Culture-18aa047bb9af800b8f6ff5f5c83174b1 Outpost founder: http://www.littlegoatlabs.com/

Outpost is where the hard problems are. If you want to build the infrastructure for global physical goods commerce, we'd love to hear from you.