Canada Market entry & commercial advice
I’m Sawyer. I help companies figure out who to sell to in Canada, how to get the conversation started, and what has to be true for the market to stick.
I’ve sold new technology to restaurant owners, built loyalty partnerships at RBC, and joined Cove as its first Canadian hire. A lot of my work starts with a buyer who’s never heard of the product. That’s the part I’m good at.
Experience across business models
Restaurant technology
Loyalty & partnerships
Commercial real estate technologyIf Canada is next
Maybe you’ve got a few Canadian customers already. Maybe your US sales team is covering Canada when they have time. Or maybe you’re deciding whether to hire someone here.
That’s a good time to talk. We can sort where the real opportunity is, which buyers are worth the attention, and what to do before you hire or pour more coverage into the wrong list.
A little context
My career has moved from restaurant technology to banking to commercial real estate. Different buyers, different reasons to say yes — and plenty of reasons to stall. The notes below are the work behind the advice, not a full CV.
I joined as Cove’s first Canadian employee to open the market for commercial real estate software — cold accounts, unfamiliar product, enterprise buying process. Canadian deals also surface tax treatment, data residency, and language questions that belong in go-to-market, not after the pitch. I’ve helped the company treat them that way.
At RBC I built partner relationships from scratch with brands including Subway, American Eagle, and Sleep Country, and grew existing ones with Apple, Lyft, TELUS, and others. The useful pattern for Canada entry: get the deal done, then stay accountable once marketing, product, and operations have to deliver.
At Ritual I sold to restaurants in Toronto and US markets, coached other sellers as a team lead, then moved into national accounts. I helped onboard and train more than 30 national chains, including groups with up to 150 franchise locations — unfamiliar product, real operators, at scale.
I helped grow Yelp’s newly acquired WiFi product and earned a promotion in under a year. Selling something unused to a busy restaurant owner is a fast lesson in getting to the point.
Working together
Bring the account list, the pitch, or the question you keep circling. You don’t need a polished brief.
We’ll look at what you sell, who buys it today, and what you already know about Canada. Then we’ll agree on a useful first piece of work — a sharper segment, a short account plan, or a clear view of whether a partner actually improves your path to buyers.
You’ll know what I’m owning and what you’ll have when we’re done. If it still makes sense to stay involved while you put it into practice, we can do that.
Tell me what you’re working on ↗The work around the sale
A launch raises questions about people, partners, and whether the commercial picture is honest. Here’s where I get involved.
I can help define the seat, pressure-test candidates, and plan the first 90 days. I’ve hired and coached sellers and managers at RBC and Ritual. The goal is a Canada hire who can actually open the market — not a vague local presence.
I help decide whether a partner is a real route to customers or a distraction, then shape the proposition and the first conversations. RBC is where I learned both sides: creating the relationship and staying responsible after the announcement.
If pipeline, forecast, or activity reporting isn’t helping you decide, I can help you see what’s noise and what’s signal — without turning this into a CRM configuration project. Custom development belongs with a specialist; judgment about the sales motion does not.
The field notes
Six decisions that turn expansion ambition into a focused commercial plan.
Read the article ↗Build a useful account list around buyer fit, timing, and a credible reason to engage.
Read the article ↗That’s the focus, plus companies already here that want sharper customer focus, a better hire, or more from a stalled partnership.
No. That’s where I work today. I’ve also worked in restaurant technology and bank loyalty partnerships. I’m most useful when the product needs explaining and the buyer won’t be rushed.
Yes. Bring one question. We can agree on a focused piece of work before talking about anything longer.
I ask a lot of questions, talk things through, and I’m fine laughing along the way. The best sales calls feel like two people working a problem — that’s the feel I’m aiming for here too.
Toronto, Ontario
A few lines is enough. What’s the business, where Canada fits, and what would help right now?
For the right Canadian GTM or partnerships leadership role, I’m open to a conversation too.