Global work brings the freedom to work for anyone, from anywhere, creating a portfolio career of opportunities that local, salaried positions can struggle to match. But global work also comes with the pain of paying and getting paid. Once the hassle of invoicing is done, late payments, exchange fees, and cross-border regulations can create an administration nightmare.
To explore how technology can change this reality, TFN partnered with a global work platform designed to help businesses, remote workers, gig workers, and contractors – Native Teams to bring together leading players in the future of work for the webinar Navigating Payments: AI-powered solutions for creators and gig platforms.
The discussion brought together operators who serve freelancers and gig workers at scale and innovators who are building next-generation financial tools.
Together, we explored how AI is tackling these pains and building a fairer financial future for the independent workforce.
The conversation featured:
- Ben Legg, CEO of The Portfolio Collective
- Jack Thorogood, CEO of Native Teams
- Stjepan Zelić, CEO of Hypefy
- Jibek Valevka, UK Head of Community at Malt
Watch the full panel video below:
The persistent pains of a portfolio career
Every freelancer faces the same issue, regardless of whether they are a content creator or a senior fractional executive. Late payments remain the biggest frustration.
“If you’re lucky, it’s 30 days. It’s often 60 or 90, sometimes 120,” said Portfolio Collective’s Legg. “And then they’ll make a mistake in the system, and it’s an extra 30 days.”
Cross-border regulations add another layer of difficulty. Native Teams’ Thorogood noted how simple payments can be in some countries, while others require detailed documentation.
“If I receive a payment here in the UK, no problems whatsoever,” he said. “But in some countries, receiving an unexpected foreign payment can raise questions, and they have to
have the paperwork to back up that transaction.”
For many workers, the challenge begins even before payment. Independent work lacks the security and safety net of traditional employment.
“They don’t have paid sick leave or guaranteed income,” says Valevka, from freelancing platform Malt. “All these unfortunately make it so much harder to thrive as a freelancer.”
These, however, are problems that come with getting work, something that freelancers cannot guarantee.
The administrative ally: AI as an operational powerhouse
The panel agreed that AI has become a powerful engine behind the scenes. At Native Teams, automation has already transformed operations.
“At the start of this year, we had 310 employees,” he said. “We’ve more than doubled our revenues, and now we have 311 employees because we’ve really invested in automation.”
Machine learning is also strengthening fraud prevention. Thorogood described their internal
“hall of shame” for people attempting to bypass checks, a reminder that AI remains essential in protecting both businesses and their workforce.
For Hypefy, AI plays an invisible but essential support role. In fact, Zelić explained how it helps guide brands when requesting revisions from creators.
“We try to point the brand in the right direction so they don’t destroy the content that the creator has built,” he said. This creates a seamless experience that customers describe simply as “easy to work with”.
As Zelić put it, “How do you know a process is good? You do not notice it. It just works.”
From payroll to partner: AI’s role in financial well-being
The panel also explored how AI could evolve from a backend engine into a proactive financial partner.
Valevka revealed Malt’s use of AI to assess creditworthiness, using that data to offer guaranteed payments to freelancers by 2026, and absorbing the risk of non-payment.
AI could even take on specialised financial tasks. Thorogood suggested a future where smart routing allows AI to optimise foreign exchange based on fluctuations.
“If you are a freelancer getting paid in US dollars and based in Armenia, and you do not need the money until next week, giving those parameters to an AI engine might help you keep more of that money because you can get better FX rates.”
Over time, Valevka sees AI simply running financial management in the background. It would handle admin, predict cash flow and support income growth without requiring constant user input.
Navigating the human and regulatory hurdles
While the benefits are significant, global companies and workers still express fears about data security and accuracy.
“There is still some fear of leaks, who has my data and what is going to happen to it,” Legg said. He added that concerns about hallucinations also matter. “We know AI makes mistakes. So will it get it all right, or will it calculate my numbers wrong?”
Some worry that AI will replace freelance roles, creating mistrust. Valevka challenged this perception. “There is generally a misconception that AI is somehow against them, which is not true,” she said. “I don’t know whether it’s the nature of us as human beings, but actually, AI will help both with better matching, but also spotting fraudsters.”
Regulation also needed to catch up, both with AI and new ways of working. Zelić referenced the situation where they had automated much of their platform, but some jurisdictions still required signed contracts.
“I had to sign every contract by hand for them to get paid. It was insanity.” Although the problem has now been addressed, it was a problem for both Hypefy and workers in some countries. “With millions in revenue monthly, I can’t be signing every $100 contract,” Zelić explained.
The need for legal protection for workers was also suggested. Legg proposed a measure that would be simple and effective. “Normally, I prefer stripping away regulation,” he said, “but it would be helpful for countries to set a limit for payment delays, like any one-person company has to be paid in 30 days.”
The inevitable rise of the independent worker
Independent work surged after the pandemic and continues to expand. Discussions once confined to niche communities are now central to the future of work. “
All forecasts say by 2030, half of all workers will be independent,” Legg said. “Any bank or payment system that does not work with this ecosystem will lose market share.”
Independent workers value autonomy but often struggle with payment uncertainty. The panel agreed that the landscape is improving rapidly. “We are definitely trailblazers here trying to solve all these things already,” Valevka said.
But she believes that where they lead, others will follow, and soon, getting paid might be the easiest part of independent work.
This content is produced in collaboration with Native Teams.
