The Invisible Software Running Behind Every International Flight — Sherpa's Story

*Recorded at StartWell - Toronto's campus for corporate meetings & events: https://startwell.co

Max Tremaine is the cofounder and CEO of Sherpa - the travel infrastructure company helping millions of travellers every week understand what they need to cross borders, apply for eVisas as an add-on inside travel bookings, and validate documents for airlines and travel operators.

In this conversation on the StartWell Podcast, Max breaks down how a painful personal travel problem turned into a global B2B platform - and why the travel world is shifting from “visa-free” to “pre-clearance everywhere” (eVisas, ETAs, and arrival systems). We also dig into the COVID-era inflection point that helped Sherpa scale from a couple airline integrations to dozens, the realities of selling into airlines and travel ecosystems, and why “hiring a bunch of people” is rarely the shortcut founders think it is.

We also get practical about AI - not as hype, but as a real operational advantage. Max shares how Sherpa uses LLMs to spot changes in government systems earlier and reduce response times from weeks to hours, while still keeping humans accountable for architecture and trade-offs.

CHAPTERS: 0:00 - Border requirements 2:00 - What Sherpa does 4:40 - The origin story 8:10 - Why eVisas and ETAs are the future of border control 15:00 - Building in a “service industry” 17:20 - The hard part 20:40 - COVID as an inflection point 25:30 - Monetization 32:30 - Venture era realities 38:40 - AI in operations