The luxury travel agency that refused to fire the humans - and put them next to the search bar instead.
A booking site does the searching. A real advisor does the caring. Skylark decided you shouldn't have to choose.
It is late. You are booking a trip you have earned. The tab is open to a five-star hotel in a city you can barely pronounce, and there are eleven room types, three cancellation policies, and a nagging feeling that the internet is hiding a better deal from you.
On most travel sites, this is where you are alone. You click, you hope, you hit confirm, and if something goes sideways at the front desk three weeks later, your only recourse is a chatbot that apologizes in perfect grammar and fixes nothing.
Skylark built a company to interrupt that exact moment. You can still do the 2 a.m. clicking - the searching, the comparing, the booking, all online. But the confirm button is not the end of the relationship. It is the beginning of one. Somewhere on the other side is a person whose job is to make sure the upgrade lands, the breakfast is free, and the front desk already knows your name.
"The only true hybrid online-offline agency: clients book online, and advisors support them by phone, email, text or chat."
For twenty years the travel industry told a tidy story: the algorithm would win, the travel agent would die, and everyone would book their own life through a search box. Skylark read that story and disagreed with the ending.
Founded in New York in 2015 and launched to the public in 2017 after a quiet beta, Skylark positions itself as the next generation of the luxury travel agency. The pitch is almost stubbornly simple. Give travelers a slick booking platform for five-star hotels and privately negotiated airfare. Then hand them a real, expert advisor for everything the software cannot feel - the spa appointment, the driver, the itinerary that changes twice before takeoff.
The result is a company that looks like a startup and behaves like a concierge. The website does the heavy lifting of search. The humans do the part that turns a booking into a trip. Neither is a bolt-on; both are the product.
It is a contrarian bet made in the most obvious way. In a decade obsessed with removing people from every transaction, Skylark kept them - and made the people the reason to come back.
Figures compiled from public sources and third-party estimates; treat headcount and revenue as approximate.
Browse five-star hotels and privately negotiated airfare, compare rates and perks in one place, and book when you are ready - even at 2 a.m.
Full-service advisors handle flights, hotels, spa appointments, guides, drivers and tours by phone, email, text or chat. Complex trip? That is the point.
Room upgrades, complimentary breakfast, resort credits and early check-in through Virtuoso membership and direct hotel partnerships.
Access to privately negotiated business- and first-class fares that often undercut the public rate you would find on your own.
"$4M in seed funding buys a lot of software. Skylark spent it proving software still needs people."
Skylark was founded by Paul Tumpowsky, who serves as CEO. His thesis, delivered in industry interviews around the company's growth, was that the luxury end of travel is more insulated from downturns than the mass market - and that affluent travelers want convenience and a competent human, not a choice between them.
That conviction shows up in the product. Skylark did not build a cheaper OTA or a fancier chatbot. It rebuilt the agency itself, browser-first, and staffed it with advisors who are meant to answer.
Paul Tumpowsky - set the "high tech, high touch" strategy and led the company through its 2019 seed round.
Membership in the luxury travel network unlocks VIP amenities at top hotels worldwide.
Headquartered at 666 3rd Avenue in Manhattan, in the thick of the travel and startup worlds.
Skylark Travel Group founded in New York.
Public launch after a quiet private beta - the hybrid booking-plus-advisor model goes live.
CEO Paul Tumpowsky shares his 2019 outlook with Travel Weekly, arguing luxury travel resists downturns.
Closes $4.0M seed round led by 25Madison, with Bessemer, BCD Travel, Ovation and others.
Traditional Virtuoso member agencies and American Express Travel on one side; newer advisor platforms like Fora Travel and online luxury players such as Mr & Mrs Smith on the other. Skylark tries to stand in the middle - software and service, together.
A New York blend of hospitality service standards and startup product thinking. Advisors and engineers pushing toward the same promise: book it online, feel it handled by a human.
Explore Skylark's own channels and coverage for demos, interviews and the booking experience.
▶ Founder interviews on YouTube ▶ Product demo & booking site ▶ Hotel reels on InstagramIt is late again. The tab is open, the eleven room types are still there, the nagging feeling still whispers that a better deal exists.
But the screen is different now. The rates already include perks you did not have to hunt for. The confirm button does not drop you into silence. And when something shifts three weeks later - the flight moves, the room is wrong, the plan needs a plan - there is a name attached to your trip who picks up.
Skylark did not remove the human from travel to make it modern. It kept the human and made the software carry everything else. The 2 a.m. moment is still yours. You are just no longer in it alone.
"The most modern thing Skylark does is answer the phone."
Profile compiled from public sources including Skylark.com, Crunchbase, PhocusWire, Travel Weekly, PR Newswire and PitchBook. Financial figures are approximate.