Jason Lalor is CEO of Conferma. Before joining Conferma, he served as chief executive of Square’s European business and as executive director on several of Square’s international boards. He previously held senior roles at Barclaycard, American Express, Dell and Mastercard.
Everyone is updating business travel for the new world of work—except payments. Bleisure isn’t a trend. It’s a shift in how modern professionals think about time, travel and value. One day it’s a fintech roundtable in Amsterdam. Next week, it’s Art Basel in Paris. A Seoul investor summit becomes a culinary deep dive. This is what purposeful, blended travel looks like today—and employers are catching on fast. Flexible policies. Relaxed approvals. Even executive encouragement to “make the most of it.”
But while HR teams are rewriting the rules and tourism boards are embracing this shift, one part of the industry is still clinging to the past: payments.
Here’s the problem: Finance systems expect every meal or taxi to fit into a tidy box labeled ‘business’ or ‘personal.’ In reality? Nearly half of business travelers extend their trip if allowed. Try explaining to finance that Sunday night’s hotel was for a Monday meeting—but the beach day on Saturday was personal.
This isn’t just awkward—it’s broken. Travelers are stuck with the admin and finance teams are left guessing. Policies are either vague or wildly over-policed. And the worst part? The tools meant to help are nowhere near fit for purpose.
And as older generations may grit their teeth and put up with it, Gen Z simply won’t. They’ve grown up with tap-to-pay, app-based banking and real-time refunds. They expect flexibility, but also clarity. They won’t tolerate blurry policies or clunky processes, so they require tools that make it easy to split work from play.
The business travel industry is starting to tackle these legacy inefficiencies head-on. Hilton, for example, became the first global hotel group to integrate virtual card payment details directly into its property management system. This removes the need for travelers to present physical payment methods at check-in, ensuring clearer boundaries between personal and business spend, with the corporate element already taken care of. It’s a small change, but a meaningful signal that legacy systems are finally being questioned.
The bleisure boom is exposing a simple truth: Travel has evolved but the financial plumbing hasn't caught up. And in a nearly US$1.64 trillion market that’s not a small oversight, it’s a strategic failure. Yet we’re still asking employees to pay out of pocket, sift through receipts, and justify every line item as if it’s 2012.
We’re still asking people to front costs, track receipts, and chase reimbursements like it’s a decade ago. Data reveals UK employees are left stressed with nearly £7,500 in expense claims every year, while 43 percent of staff struggle with personal bills due to delayed reimbursements. That’s not sustainable.
Virtual payments change this outdated reality. They draw clean boundaries between spend categories and automate tedious admin. When a virtual card is generated, it's linked to a specific spend purpose, meaning transactions can be automatically categorized—for example, separating hotel bookings from ground transport. They give finance teams near real-time oversight, so no one’s left reconciling a spreadsheet three weeks after the fact.
Most of all, they give people options. The freedom to travel in a way that works for them, without making it harder for finance teams to do their jobs. That’s the gap fintech needs to close.
If bleisure is the new look of flexibility, payments can’t be the weak link and the way we pay for it shouldn’t be stuck in the past. If we’re serious about modern travel, it’s time to modernize the money.