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 border

In 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.

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 Canada
• How federal vs provincial tax structures work
• Why Canadian taxes and cost of living factors into comp strategy

Benefits aren’t “copy/paste” across the border We talk through subtle but important differences, including:

• Maternity/parental leave expectations
• How stock options are taxed and perceived in each country
• Why your benefits need to be right-sized for each country

Culture, trust, and risk tolerance: the stuff the setup guide doesn’t tell you
This is the part you won’t get from your EOR or payroll provider:

• Importance and challenge of building trust
• Why Canadian teams often put more emphasis on relationship and intention before diving into numbers
• How risk appetite differs

Tech, fintech, and cross-border payments
We touch on the reality of:

• Why data residency, AML, and server location matter if you’re a SaaS or fintech selling into Canada
• How upcoming open banking in Canada (2026) could unlock new ways to move money and serve customers cross-border

A 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

You don’t have a “lead problem.” You have a go-to-market alignment problem that’s quietly capping your growth.

In this mini-panel, we dig into why revenue plateaus at growth-stage B2B companies usually aren’t about “more pipeline” – they’re about sales, marketing, customer success, product, and finance all pulling in slightly different directions.

No scolding. No “you’re doing it wrong.” Just four operators and advisors comparing notes on what actually works when you want healthy, scalable revenue, not just a noisy top of funnel.

• Why “sales & marketing alignment” is table stakes now
  And why the real unlock is treating CS, product, and finance as part of one revenue team, not downstream order takers.
• The KPI trap that keeps teams stuck in silos Marketing measures activity, sales measures outcomes, CS measures retention—and almost no one agrees on what a qualified lead actually is.
• Customer success as your GTM secret weapon How involving CS before the sale changes who you sell, what you promise, and how long customers stay—without adding more headcount.
• Product is not your feature factory What happens when sales keeps asking for “one more feature to close this deal” and product’s roadmap gets held hostage by short-term revenue.
• Finance as a growth partner (not the ‘no’ department) How to get your CFO to trust your forecast so they’ll actually support your GTM investments instead of blocking every new idea.
• Practical ways to build internal bridges (starting this week) From “bridge coffees” to shared rituals, internal problem statements, and walking a mile in each other’s roles.

This conversation will land especially well if you’re:

• A B2B founder / CEO stuck at a revenue plateau and wondering if it’s really “just pipeline.”
• A CRO / VP Sales / VP Marketing tired of attribution fights and ready to build one revenue system instead of parallel empires.
• A Head of CS, Product, or Finance who knows you impact revenue but keeps getting brought in too late.
• Any GTM leader who wants to turn internal friction into a real competitive advantage.

By the end, you’ll have:

• A more honest way to talk about GTM misalignment without blaming people or departments.
• A simple starting point for shared KPIs that don’t trigger instant defensiveness.
• Language you can use with your CFO, CMO, CPO, and Head of CS to shift from “that’s your problem” to “this is our system.”
• A few stealable rituals (like bridge coffees and cross-functional problem statements) to start stitching teams together without a giant reorg.

Jay Brandon Daniel Shimon

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When founders decide “it’s time to grow,” the first instinct is often: “We need a salesperson.”

But your first sales hire is too important (and too expensive) to toss in the deep end and hope they swim.

In this mini-panel episode of Revenue Remix, host Summer Poletti sits down with frequent collaborators JMS (John Mason-Smith) and Sean Parnell to unpack what really needs to be in place before you add that first sales rep.

• Why “I want to grow, so I’ll hire a salesperson” is a broken equation JMS explains why half the time, when a founder says “I need a sales rep,” the real answer is: “You need a sales process, not a salesperson.”
• How founders accidentally attract the wrong salespeople Summer and Sean talk about “job-hopper reps” who are great at selling themselves into a role… and then never close meaningful business — especially when there’s no process, no messaging, and no coaching.
• Lazy, or just lost? What’s actually going wrong with new reps JMS shares the story of a rep who was “working hard” but making 10 calls a day instead of 100 because he had no guidance on what mattered and what didn’t.
• The two big levers in any sales system Volume in at the top, conversion out the bottom. If you’re not measuring these (and the steps in between), you’re guessing — not managing.
• Why founder-led sales and rep-led sales are not the same game Founders close with trust, relationships, and gravitas. Your first rep doesn’t have that halo. Expecting them to hit your close rates and sales cycles without support is setting them up to fail.
• What “good” looks like before your first sales hire
  • Clear revenue goals that are more specific than “more”
  • A basic offer, ICP, and messaging that resonates
  • At least a sketch of a repeatable sales process
  • Leading indicators defined and tracked
  • A plan for coaching, not just “sink or swim”
• How marketing, content, and AI support your first rep
  Sean dives into why cold outbound with no brand, no demand, and no content is almost always a losing game — and how thoughtful marketing + smart use of AI can keep your rep focused on the right activities.
• The pre-mortem: how to spot failure before it happens
  JMS introduces the idea of a “pre-mortem” and how founders can use AI or trusted collaborators to stress-test their plans before hiring.
• Why founders need help focusing on what they’re bad at, not just what they love
  The group talks about coaching, business mentors, and using AI as a brutally honest sounding board instead of a cheerleader.

If you’re a founder thinking about that first sales hire — or wondering why the last one didn’t work out — this episode will help you feel more confident and a lot less alone.

JMS is the founder of Hirewith, a niche hiring platform for the HCM and payroll industry. He’s a former top rep who now helps founders think clearly about when (and whether) they’re truly ready for a sales hire.

👉 Connect on LinkedIn

Sean is the founder of InnovAxis, a B2B marketing firm. He’s obsessed with measurable strategy, leading indicators, and building marketing that makes sales easier instead of harder.
👉 Connect on LinkedIn