I Wish I Knew with James Sampson | Proudly Supported by Proxi & Kea

Proudly powered by Proxi & Kea

Join us for a night with James Sampson, Founder & CEO of FileInvite — one of NZ’s great SaaS success stories.

Building a company isn’t one big “ta-da” moment.. it’s a long game. Messy middles, surprise pivots and those classic 2am “what now?” thoughts all come with the territory.

That’s what our I Wish I Knew series is about. Real talk with founders who’ve been in the trenches. They’ve taken hits, made tough calls, and still turned up the next day. Expect the kind of lessons you only learn by doing (and sometimes by getting wrong first).

If you’re a founder, part of an early-stage team, or a leader who’s serious about growth, this is for you. We do screen registrations to make sure the room’s filled with people who’ll get and give value.

James Sampson has lived the startup rollercoaster. He cut his teeth co-founding Zyber, a Deloitte Fast 50 web agency, before diving headfirst into SaaS. Out of sheer frustration with chasing documents came FileInvite, a simple idea that’s grown into a global platform making secure document collection easy for businesses everywhere. Along the way he’s won awards, raised capital, exited companies and weathered the kind of “will this even work?” moments every founder knows too well. James brings an honest and insightful perspective on building, scaling, and proving that global SaaS companies can be built right here in New Zealand.

Proxi helps Kiwi SaaS and tech companies grow faster and smarter. Their fractional go-to-market leadership spans marketing, sales and customer success, with flexible programs designed to slot in where you need them most.

From strategy through to execution, Proxi’s focus is on unlocking growth and leaving behind lasting capability inside your team.

Kea is New Zealand’s global whānau, connecting 500,000+ Kiwis across 185 countries. Their mission? Harness the smarts, skills and goodwill of offshore Kiwis to give back to Aotearoa, while making sure expats stay connected and supported no matter where in the world they are.

Think of Kea as the world’s biggest Kiwi network, helping businesses tap into global know-how, and helping Kiwis overseas keep their ties to home strong.

Venue: The Commons, 1 Albert Street, Auckland City

By signing up, you’re also joining the Caffeine Community (welcome aboard!) and we’ll share your details with our partners. Heads up: we’ll be taking photos and video on the night for socials. If that’s not your thing, just let the crew know when you arrive.