'I Wish I Knew' with FileInvite founder James Sampson
Plus: The rumblings of a coming crash are getting louder.
Kia ora Caffeinators,
Happy Wednesday arvo! Tickets going quick for our latest in person even with James Sampson from FileInvite so get in quick.
Here’s what’s brewing in your Daily Shot:
Event: I Wish I Knew with James Sampson
Loans vs Equity vs Self-Funding: Your NZ Business Funding Options Explained
Sponsored - Work Without Borders: How Remote Built the Infrastructure for Global Hiring
The rumblings of a coming crash are getting louder
As always, thank you to everyone who has upgraded to a paid subscription or simply recommended Caffeine to friends and whānau. We couldn’t do any of this without you.
Finn and the CAFFEINE team
Event: I Wish I Knew with James Sampson: Join us for a night with James Sampson, Founder & CEO of FileInvite — one of NZ’s great SaaS success stories.
About the event
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.
About James
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.
About Proxi
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.
About Kea
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
Get your tickets here and remember your promo code CAFFEINEFRIENDS
Loans vs Equity vs Self-Funding: Your NZ Business Funding Options Explained: I had a great time interviewing Bizzy co-founder Corinna Stukan a while back and it’s been great to see them growing after their official launch. They’re also publishing a great series of blogs which I highly recommend to founders pondering their options when it comes to funding. This one from Mike Burke breaks down the strengths and weaknesses of the major sources in a really digestible, actionable way which I appreciate. Check it out here.
Work Without Borders: How Remote Built the Infrastructure for Global Hiring: Like most great startup stories we cover at Caffeine, this one starts with a founder identifying a universal pain point: Global talent was everywhere, but hiring it was a nightmare.
Job van der Voort was VP of Product at GitLab, now famous for being the world’s largest fully distributed public company. GitLab’s team stretched across 67 countries, but every new hire outside its home market brought a wave of friction like legal, payroll, and tax rules that shifted with each border crossed.
“It should have been simple,” van der Voort recalls. “Hire the best person for the job, wherever they live. Instead, it turned into a maze of regulations and months of paperwork. The friction was systemic.”
This global pain point inspired Remote, the company he co-founded with Marcelo Lebre in January 2019. Their mission was straightforward but ambitious: to open the world for every person, business, and country by removing the obstacles that prevent companies from hiring globally.
The seed for Remote was planted during van der Voort’s GitLab years, but it sprouted when he connected with Lebre, then VP of Engineering at Unbabel. Both had faced the same challenge: wanting to hire great talent, but being blocked by outdated systems and opaque laws.
“When Marcelo and I compared notes, it was obvious this wasn’t a GitLab problem or an Unbabel problem - it was everyone’s problem,” says van der Voort. “We realised companies all over the world were dealing with the same barriers. We decided to build the solution.”
That solution became Remote: a platform that allows any business to hire, pay, and support talent in countries where they don’t have a local entity. By shouldering the compliance and infrastructure burden, Remote lets companies focus on the simple (and most rewarding) part - hiring the best people.
“Our goal from day one was to open the world,” van der Voort says. “We want to create opportunities everywhere and help people access work that supports the life they want to live.”
For Remote’s founders, the “aha” wasn’t a sudden spark but the repetition of the same frustration.
“I saw how long it took to set up legal entities,” says van der Voort. “Months would pass, costs would mount, and compliance risk would grow. Something that should have taken days, like onboarding a new teammate, stretched into quarters. That stuck with me.”
Lebre had faced similar delays while scaling engineering teams at Unbabel. Together, they envisioned a platform that stripped away the complexity and allowed companies to operate without borders.
“That’s the moment Remote was born,” van der Voort explains. “The idea wasn’t just about technology - it was about access. We wanted to unlock work for people everywhere and make distributed teams sustainable.”
“Millions of people have the skills and ambition to join global teams, but they’re limited by where they live,” says van der Voort. “Companies want them, but the infrastructure to hire them safely and legally doesn’t exist. That’s the gap we’re closing.”
The platform now covers the entire spectrum of global employment. Companies can use Remote to hire employees in countries where they lack a legal presence, pay them in compliance with local tax and labor laws, and manage benefits, leave, and equity. For contractors, the system automates invoicing and ensures payments flow seamlessly across currencies and borders.
“At its core, Remote is about access,” van der Voort says. “Access to talent for companies, and access to meaningful work for individuals.”
One of the most common questions Remote gets is how the solution scales. For van der Voort, that’s the point: the company is built to make scaling easier, not harder.
“Most businesses hit a wall when they start expanding internationally,” he explains. “Every new market means a new legal entity, a new set of compliance risks, and more overhead. Remote removes all that by owning and operating entities in key markets ourselves. That way, our customers don’t need to.”
Remote’s unique advantage is owning and operating legal entities across key markets — and combining that infrastructure with automated workflows like onboarding, payroll, and benefits.
“In short, we let companies scale globally without growing in complexity,” van der Voort says.
Remote is expanding beyond EOR into a unified global employment platform — combining payroll, HRIS, contractor management, and compliance into one trusted system..
“Our focus is becoming the default platform for global employment,” van der Voort says. “That means moving beyond EOR to a full suite of HR and payroll solutions.”
The aim is to give companies one trusted system to manage everything from onboarding and benefits to payroll and compliance. According to van der Voort, that direction is being driven by customer demand: “Businesses want fewer systems, faster hiring, lower costs, and more confidence. We’re building to meet that.”
For workers, Remote is also investing in the overall experience —ensuring that accessing global opportunities also comes with stability, equity, and fair treatment.
“Access isn’t enough on its own,” he says. “The experience matters too.”
For businesses, the value proposition is clear: faster hiring, reduced risk, and the ability to grow in new markets without building out costly infrastructure.
But the part van der Voort finds most meaningful isn’t on the corporate side.
“What’s most gratifying is seeing the impact on individuals,” he says. “When someone gets hired through Remote, they gain financial stability, career growth, and the ability to live where they choose. That’s life-changing. That’s why we do it.”
Asked what other founders can take from Remote’s journey, van der Voort stresses practicality over glamour.
“Think globally from day one, but solve real problems at a human scale,” he says. “Remote wasn’t built around a flashy idea - it was built to fix a painful barrier companies were facing. We focused on delivering real value in a space where trust and precision matter.”
He also underscores the importance of infrastructure. “Scaling isn’t just about user growth. It’s about building the systems that make growth sustainable. That’s especially true when you’re dealing with people’s livelihoods.”
One lesson he wishes he’d learned earlier? Pacing.
“Building a company is a marathon in every possible way,” he says. “It’s easy to fall into the trap of sprinting in the early days. But sustainable growth comes from pacing yourself, building resilience, and giving yourself the time to do it right.”
Though headquartered globally, Remote has been watching the New Zealand startup ecosystem closely.
“What excites me most about New Zealand is the global mindset,” van der Voort says. “Despite its size, the ecosystem produces innovation in agritech, AI, healthtech and more, backed by strong values and early-stage funding. It’s a market aligned with our mission - unlocking access to talent and opportunity.”
To support that ambition, Remote is extending an offer to local founders: a 15% discount for startups using the platform (use offer code: AFCAFD15, valid until 31 December 2025.)
“We want to invest in the next generation of global companies,” van der Voort says. “If you’re building a startup with global ambition, you don’t need to wait to hire globally. We’ll take care of the complexity—so you can focus on your product, your team, and your customers.”
Remote’s rise is part of a broader shift in how the world thinks about work. The pandemic accelerated demand for borderless hiring, but the forces driving it—globalization of talent, digital connectivity, and demand for flexibility—aren’t going away.
For van der Voort and Lebre, the mission remains the same as when they started: to make global work accessible to everyone.
“Our vision is simple,” van der Voort says. “We want to make it as easy to hire someone across the world as it is across the street. When that happens, borders stop being barriers and talent everywhere has the chance to thrive.”
This post was written in partnership with Remote
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The rumblings of a coming crash are getting louder: The familiar warnings of a near apocalyptic crash are getting louder and more urgent. This is something we can parse in a bit more detail tomorrow, our usual slot for global news, but think its definitely worth giving this (free) blog from Cory Doctrow a read if you want to get up to speed on some of the basics. Essentially, the world economy is a Jenga tower balanced on a shrinking number of blocks and it is only going to take a relatively gentle nudge to send the whole thing crumbling. The FT also did an excoriating piece with the headline ‘America is now one big bet on AI’ showing how an astonishing 40% of GDP growth in the nation is down to AI spend. I am no economist but I feel like the globes fortunes shouldn’t depend on a number of companies I can count on one hand.
That’s it for today, thanks for reading. Want to get in touch with a news tip, bit of feedback or just to chat? Email hello@caffeinedaily.co