Navigating Talent and Compensation Across Borders

What happens when you pack a carry-on, fly across the world, and try to scale a healthcare startup in one of the world’s toughest markets?

In the latest episode from our Operator series of Wild Hearts, we sit down with Jesse Creighton, Director (US), Heidi Health.

Jesse shares what it really looked like to launch the company’s American expansion — from hosting awkward dinners with two doctors at a 20-person table to building a high-performing sales team with its own unique culture in New York.

In this conversation, we cover:

🗽 What it was like being the first on the ground in New York to launch Heidi in the US

🎯 Why Heidi's initial customer outreach flopped — and what they learned from it

🧠 How freemium became a game-changing growth strategy in healthcare

🛠 Why product-market fit in the US required rethinking sales, support, and compliance

🌎 The role of generalists vs. specialists when building early-stage teams across markets

🎥 How customer obsession and Aussie culture helped shape Heidi’s US team

📈 The two biggest bets that paid off — and why most investors didn’t see them coming 

This episode is a masterclass in how to scale a startup across borders — blending instinct, experimentation, and a deep belief in product.