Chris Tomkins assumed he'd never get the job. A neighbour — a repeat Virgin Voyages cruiser — sent him the listing for Virgin's first-ever Head of Yes, and his instinct was to dismiss it entirely. Weeks later, his dad talked him out of that mindset, and Tomkins applied. He got it. Speaking to Matador CEO Ross Borden on CREATOR: The Podcast, he described the surreal half-year that followed.
It started before he even left home: Virgin sent a bagpiper to his front door in Newcastle. Over the following six months, the role turned into exactly what the title promises — a paid, full-time commitment to saying yes. Tomkins found himself persuading a complete stranger to hop in a helicopter over New York City, and sailing aboard a Virgin Voyages ship where Sir Richard Branson personally set aside time for a coffee with him.
The gig reportedly comes with a $100,000 package for the six months, and now Virgin is recruiting its second Head of Yes. The big change this round: applicants from the United States are eligible, alongside candidates from the UK. The job is essentially a content creator role with teeth — someone willing to be dropped into unfamiliar situations, take the leap every time, and document it convincingly.
For travellers, this is more than a gimmick. It's a signal of how Virgin wants to position its voyages: spontaneous, sociable, and slightly absurd in the best way. The stunts Tomkins was sent on — a piper at the door, helicopter rides, coffee with the founder — map onto the experience Virgin Voyages sells to paying guests: an adults-only cruise line that trades buffets and formal nights for late-night entertainment and unexpected moments.
Applying is worth considering even if, like Tomkins, you're convinced you have no chance. He nearly deleted the listing. The only reason he got the job of a lifetime was a nudge from his dad a few weeks later. Virgin is looking for personality and willingness, not a CV full of cruise experience — so the barrier to entry is lower than it looks. If a paid six months of travel, American applicants now welcome, sounds better than your current job, it may be time to send in the application before the window closes.
