Your First Global Step: The Right Way To Do Business Across the US–Canada Border

Your first global step probably isn’t opening an office in London or Singapore. For most North American growth-stage companies, it’s something simpler:👉 A fantastic candidate in Toronto👉 A customer in New York who wants local support👉 A test market just across the borderIn this panel, I’m joined by Toronto-based leaders Eric Hachmer and Komal to unpack what it really takes to operate across the US–Canada border — beyond “just add a worker” in your payroll platform.We talk about why Canada is often the first global footprint for US businesses (and vice versa), and how to do it in a way that supports long-term growth instead of creating messy cleanup work for future you.We cover:Why “just hire someone in Canada/the U.S.” is not a global strategy We start with the common story: a key employee moves to Toronto, or a US founder decides “Canada seems easy enough.” Eric and Komal walk through the gap between employing someone cross-border and actually doing business in another country.Structure before headcount: what to decide before you hire Eric shares why hiring is the easy part — and why your go-to-market model, sales design, and leadership attention matter far more than how quickly you can add someone in your payroll tool.Incorporation, tax, and comp 101 (without putting you to sleep)Komal breaks down:Why you should think about incorporation in CanadaHow federal vs provincial tax structures workWhy Canadian taxes and cost of living factors into comp strategyBenefits aren’t “copy/paste” across the border We talk through subtle but important differences, including:Maternity/parental leave expectationsHow stock options are taxed and perceived in each countryWhy your benefits need to be right-sized for each countryCulture, trust, and risk tolerance: the stuff the setup guide doesn’t tell youThis is the part you won’t get from your EOR or payroll provider:Importance and challenge of building trustWhy Canadian teams often put more emphasis on relationship and intention before diving into numbersHow risk appetite differsTech, fintech, and cross-border paymentsWe touch on the reality of:Why data residency, AML, and server location matter if you’re a SaaS or fintech selling into CanadaHow upcoming open banking in Canada (2026) could unlock new ways to move money and serve customers cross-borderA more hopeful take on “messy times” We close on why business leaders are often the ones quietly building bridges while politics gets loud — and how thoughtful, generous leadership and clear decision-making can make cross-border work a growth engine, not a headache.If you’re a founder, CRO, CMO, or finance/ops leader thinking:“Canada feels like the logical first place to go global… but I don’t want to step on a landmine.”…this episode will help you see what’s really involved, what’s easier than you think, and where it pays to slow down and set things up right.👉 Connect with Eric👉 Connect with Komal