Selling Into the US? 5 Questions Before Your First Invoice

Why it matters now

Before entering a new country, it pays to bring tax, legal and finance into the decision. Checking the numbers before the first invoice helps protect margin and cash.

Since late August 2026, the US has added tariffs on certain Canadian goods, changed the products covered and banned some imports. For affected products, a price set in the spring may now be losing money.^[2]

US states can require remote sellers to collect sales tax once applicable thresholds are met, even with no office or staff there. Compliance adds cost, and missed collections can become the seller’s liability.^[3]

This is also a financial decision

A US opportunity can start with a customer saying yes. Before the invoice goes out, the owner needs to ask what the move costs, what it risks and what it returns.

That is the lens we use at Bibeka Advisory. The decision to enter stays yours. Our job, as a CPA (NY)-led advisory, is to make sure it rests on your numbers, not on the first purchase order.

Five questions to answer before your first invoice

1. 1. Do you have a taxable presence in the US?

   Your activities in the US can create tax-filing obligations even when the treaty protects your business profits from US federal income tax. Selling to US customers does not, by itself, settle the question. State taxes require a separate review.^[4][5]

2. 2. Do you need to collect sales tax, and in which states?

   States set different remote-seller thresholds, and the rules change. Whether you must collect also depends on what you sell, applicable exemptions and whether a marketplace collects on your behalf. A missed registration can mean paying tax you never collected.^[3]

3. 3. Which structure do you sell through?

   Your Canadian company, a US subsidiary or something else. Each choice changes how profit is taxed and how cash comes home. Differences between the two countries’ rules can limit relief from double taxation.^[5][6]

4. 4. What does it really cost to deliver your product or service in the US, and who pays it?

   For goods, include applicable tariffs, duties and brokerage. For goods and services, factor in currency, payment terms and the cost of delivery. These costs sit between your price and your margin.

5. 5. Who works where?

   Travelling staff, US contractors and remote employees can create tax, payroll or immigration obligations, depending on their activities and status. Where the work happens is a key part of the review.

One structure that deserves extra care

It is the US LLC. It can be a sensible choice for a US owner, but a Canadian owner needs a cross-border review before choosing it. The US generally treats a single-member LLC as disregarded and a multi-member LLC as a partnership unless it elects corporate taxation. Canada treats an LLC as a corporation.^[7][8]

That can create a mismatch between Canadian and US tax treatment. The countries may tax different taxpayers or recognise income differently, which can limit foreign tax credits and create double taxation. The outcome depends on ownership, tax residence and the LLC’s US tax classification.^[6][7][8]

Timing can be part of the problem, but it is not the whole explanation. Some foreign business tax credits can be carried to other years; that does not resolve every LLC mismatch. We will cover how owners handle this in the next piece.^[6]

Before you send that first invoice

Ask yourself three questions:

• If a US customer paid you today, do you know which Canadian and US tax and filing obligations could apply?
• Do you know your margin on a US sale after delivery costs, applicable tariffs and duties, and currency?
• Was your US structure chosen with both your Canadian and US tax positions in mind?