Raiseaway

Raiseaway sells and books trip packages, and every package ends with the same deliverable: a trip itinerary for the client. Loren, then a Guest Experience Manager on the booking team, owned that process.

The itineraries lived in PowerPoint. Every trip meant reformatting a deck, exporting it, and emailing the client a PDF — and every change to a booking meant doing it again and sending a replacement file. Clients ended up holding several versions of the same document with no way to know which one was current.

The work underneath the deck was already heavy. Raiseaway scores its packages by workload on a 1-to-5 scale, and the Ultimate Irish Road Trip sits at a 5: seven days, four hotels, five activities and a car rental, all to be booked and then assembled by hand. A colleague working through that kind of itinerary end to end could finish roughly two in four hours.

When the team started building the itinerary generator itself with Claude, the bottleneck moved. Generating an itinerary was no longer the hard part — the question was where the finished thing should live. Saving it to a shared drive wasn’t it. Loren, who had run a blog years earlier and knew the hosting space, wanted a real, live link.

ChatGPT made the introduction. Loren had taken to prompting it as a stand-in CTO — “I’m looking for this kind of service to simplify the inefficiency” — and it came back with a comparison of Tiiny Host and Netlify, with Tiiny Host as the option that scales with the business.

The generator itself is a single HTML file, built with Claude, that lives on Netlify and is open to the whole booking team. Publishing is where Tiiny Host comes in: the generator is wired to the Tiiny Host API, so every itinerary the team produces is pushed live automatically. Nobody uploads anything by hand.

The detail that mattered most wasn’t in the original brief. Regenerating an itinerary through the same API key republishes to the same URL instead of minting a new one. When a client’s schedule changes, the team doesn’t send a new file or a new link — they tell the client the link they already have is updated.

That also set the hosting requirement. Clients book months ahead, so an itinerary published in August for a trip in December has to stay live the whole way. Raiseaway moved onto Pro Max for unlimited projects and links that stay up as long as the trip needs them.

The team’s verdict on the platform itself was that there wasn’t much to learn. “It’s very user-friendly. It’s very simple, very self-explanatory — which I like the most. When I go to Tiiny Host Manage, all your projects are here. It’s live.”

Itinerary time was cut by at least half. The booking team pulls a preset template from the CRM where most of the package is already filled in, adds the times and booking confirmations, pastes it into the generator and publishes. “If we are doing an itinerary for an hour, it’s now half an hour.” On the heaviest packages, the ones rated 5 out of 5, the saving is larger still.

The reaction internally was immediate — “this is a game changer, because it saves them a lot of time” — and the pattern started spreading. Trip FAQ documents, still going out as email attachments, are the next thing the team expects to publish as links rather than PDFs.

It changed Loren’s job, too. The itinerary project became one of the things on the résumé for an internal move, and the promotion came through the week before this call: Guest Experience Manager to Business Operations Manager, with the inefficiencies of every team now in scope.

“It’s one of the things I put into my résumé when I applied for business ops — I got introduced to this platform. Great experience so far with Tiiny Host.”