Cross-Border Exit Planning: Structuring a Sale Across Jurisdictions

A domestic exit is structurally straightforward: one jurisdiction, one tax authority, one set of rules. The founder sells, the gain is calculated, the tax is paid. The variables are known in advance. A cross-border exit operates under fundamentally different conditions. When the entity is formed in one country, the founder resides in another, and the buyer operates from a third, the sale triggers tax events in multiple jurisdictions simultaneously. Each jurisdiction applies its own rules to the same transaction, potentially claiming the right to tax the same gain.

The structural complexity of a cross-border exit is not the exit itself. Selling a business follows a recognizable pattern regardless of geography: negotiation, due diligence, closing, payment. What changes entirely is the intersection of entity structure, tax residency, treaty provisions, and sale structure that determines how the proceeds are actually taxed. A founder who built a profitable SaaS company through a Delaware LLC while living in Lisbon and selling to a Singapore-based acquirer faces not one tax calculation but several, each governed by different rules, different rates, and different definitions of what constitutes a taxable gain. The exit crystallizes every structural decision made over the life of the business into a single, high-stakes transaction.

Key Takeaways