Strategy & Operations (Logistics)

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 started with digital goods: tax compliance, merchant of record, liability transfer. Now we’re building the infrastructure for physical goods cross-border commerce including customs duties, landed cost calculation, DDP/DAP routing, import VAT, and clearance operations. Sell anything, anywhere. Without compromise.

This is an Operations role for someone who deeply understands what happens when physical goods cross borders. You know the difference between customs, duties, tariffs, and import VAT. You understand why HS classification is hard at scale. You’ve seen what actually goes wrong at clearance. You know when DDP beats DAP on unit economics. You’ll work directly with the CEO to scale Outpost’s physical goods capability. We’ve built the foundation; now we need someone to take it further. That means solving the hard problems: landed cost accuracy at checkout, HS classification at scale, DDP routing logic, carrier/broker orchestration, and merchant onboarding. You’ll also work across the business (GTM, product, partnerships) because that’s how early-stage companies work. We want someone who’s lived this problem, ideally at a cross-border platform, e-commerce merchant, or logistics company.

What You’ll Get

Yes, the work is intense. But in return, you’ll get the chance to build category-defining infrastructure from scratch. Cross-border e-commerce is a massive market with broken tooling. You’ll shape how physical goods infrastructure gets built at Outpost, not just operate someone else’s system.

What You’ll Do

• Landed Cost & Checkout
  • Build the systems that calculate duties, tariffs, and import taxes accurately at checkout
  • Solve HS classification at scale and get the right codes for merchant product catalogs
  • Ensure landed cost accuracy so DDP doesn’t bleed margin or surprise customers
• DDP/DAP Strategy
  • Build the routing logic that decides when to absorb duties (DDP) vs pass through (DAP)
  • Optimize by order value, margin, product category, and destination market
  • Understand de minimis thresholds and when simplifications apply (IOSS, UK low-value)
• Customs & Clearance Operations
  • Own carrier and broker relationships with DHL, FedEx, UPS, and postal services
  • Ensure goods clear customs reliably without delays or customer friction
  • Handle clearance failures, documentation issues, and stuck shipments
  • Build the documentation infrastructure including commercial invoices and certificates of origin
• Returns & Recovery
  • Build duty drawback processes to recover duties when goods return
  • Handle import VAT recovery on returns
  • Manage refused deliveries, abandoned parcels, and partial refunds
• Merchant Onboarding & Platform Integration
  • Onboard merchants from Shopify, WooCommerce, and BigCommerce
  • Get product data structured for classification
  • Configure checkout flows for DDP presentation
  • Integrate with merchant fulfillment and order systems
• Cross-Functional Work
  • Work with product to shape the roadmap based on merchant pain
  • Support GTM by helping close deals and build merchant playbooks
  • Build processes and documentation that scale

Example Projects

• Build an HS classification framework for a merchant's 10,000-SKU catalog
• Design the landed cost calculation logic for UK and EU markets above de minimis
• Negotiate carrier account configurations that align with our liability model
• Create DDP vs DAP routing rules based on margin thresholds by market
• Onboard a Shopify Plus merchant onto Outpost's cross-border infrastructure
• Build a duty drawback process for high-return categories (apparel, footwear)
• Debug why shipments are getting stuck at German customs and fix the root cause
• Develop pre-checkout duty estimation that’s accurate within 2%

What We’re Looking For

Ideal background:

• Cross-border e-commerce platforms (Global-e, eShopWorld, Flow Commerce, Passport)
• Landed cost / duty calculation (Zonos, Avalara Cross-Border)
• E-commerce platforms (Shopify Markets, BigCommerce, WooCommerce ecosystem)
• Logistics with customs exposure (Flexport, DHL Trade, UPS Customs Brokerage)
• Retailers running cross-border at scale (ASOS, Farfetch, Zalando, Nike)

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’ve dealt with customs clearance failures and know what actually goes wrong
• You understand when DDP beats DAP on unit economics
• You’ve worked with Shopify/WooCommerce merchants or integrated with those platforms
• You know how cross-border platforms structure their model

Bias for action: you solve, not observe. Comfortable with ambiguity because startups are not neat.

What this role is not:

• Not a pure logistics/warehouse role
• Not customs brokerage paperwork
• Not strategy without operational depth
• Not someone who needs defined processes to be effective

Why This Role Is Different

Cross-border physical goods is one of the hardest operational problems in e-commerce. Most platforms are enterprise-only, slow to implement, and built on legacy architecture. We’re building something different: API-first, self-serve, programmable. This isn’t joining a mature team to run existing processes. This is scaling the infrastructure that lets any e-commerce merchant sell globally with duties and taxes handled.

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
• World-class training from operators who’ve scaled globally
• 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, especially ones involving customs edge cases and merchant onboarding, are solved in the room.

Reach Out

emile@outpostnow.com

Learn more about Outpost Culture

Outpost is where the hard problems are. If you want to build the infrastructure behind global e-commerce, we’d love to hear from you.