Reflections on building AI for hospitality

While heads down building, I made it out to The Hospitality Show in Denver. Unsurprisingly, the topic of the week was AI, AI, and more AI.

Even walking the tradeshow floor, it felt like every vendor had "AI-powered" somewhere on their booth. Even pillowcases and soap are AI-powered these days! (half kidding 🫠)

It's dizzying. I can only imagine how property teams and operators feel trying to make sense of it all. So I wanted to share a few reflections from building in the field.

Notes from the field

AI agents are the new websites

Having an AI agent is quickly becoming the new version of having a website. It will be the standard for how people discover and engage with your business, as discussed in The new white pages are coming.

However building an AI agent isn't plug-and-play. It takes time and iteration to train it and teach it how your business works. Its value is directly tied to the quality of the onboarding.

Technology is only as good as the problem it solves

Balaji Srinivasan has a great observation: "AI is not yet end-to-end, but middle to middle". What that means is that it doesn't invent its own purpose or redesign workflows on its own. It still needs guidance. It needs people who understand the context and can steer it toward the right problems.

The value comes when AI is applied to specific pain points and workflows that actually matter, not when it's added as a marketing label. Buyer beware: check the ingredients list closely. Is it solving something real under the hood, or is it just a sticker?

AI isn't taking your job, but those who use it will

In the 90s, people used fax machines. In the 2000s, they used email. Would you hire someone who still uses a fax machine? The market has always rewarded people who bring value with efficiency and improved communication. This is no different.

A hospitality renaissance

Ari Emanuel, CEO of Endeavor, has been making big bets on IRL entertainment. In this talk / and article he outlines how culture is shifting toward shorter work weeks and greater demand for entertainment and IRL experiences. One data point he mentioned stood out to me: the sharp increase in Thursday hotel bookings for leisure travel.

That's a sign of something bigger that we're betting on, too. As life moves more online and isolation grows, the desire for IRL connection will only rise. Hospitality has always been here to meet that moment. It's an industry built on creativity, service, and memory-making, all things people will continue to crave and will become more valuable than ever.

Technology and AI can play a powerful role here, by removing the friction of repetitive work and giving time back to what matters. As one of our customers put it, "AI gives me time back for the creative things I love, like improving our service and designing new menus".

This is the way.

UX and guest feedback notes

Usually, you can look at other products as a point of reference for interaction design, but in this case, the traditional RFP workflow is so dominant that what we're building feels like quite a contrarian interaction. We've been running user tests to better understand how people feel when engaging with this new kind of workflow. Here are a few things we're noticing:

Get to the point

When guests reach out to a property, they're usually looking for three things:

• Pricing
• Availability
• Vibe, or simply, is this place right for me?

In observing the guest through their inquiry workflow, they consistently preferred the conversation that got straight to the point. It reflects the same frustration people have with long forms or slow responses: too much friction before getting an answer.

We're training the agent to be more of a matchmaker, not to mimic small talk or rote questioning. The human warmth and connection belong in person, during the site visit, where it naturally shines. Before that moment, what matters most is helping people get to the point.

Chat feels natural

When people first interact with the agent, you can see it's a familiar interaction, "oh, it's like ChatGPT for the property" was something we heard multiple times. They start typing, scrolling, and exploring without hesitation.

They use it the same way they might ask, "where should I have my wedding?" except now they're asking, "why should I have my wedding with you?" This pattern is familiar, intuitive, and already how people find answers today.

Visualizing the conversation

The big winner in testing was contextual imagery during the conversation. Across all sessions we saw prompts like, "show me more pictures", "what does that look like?" or "I like the outdoor option".

This fills a gap that's often missing in the classic sales phone call. The agent might say, "Oh, I think the Grand Ballroom would be a great fit", but what that looks like is left to the guest's imagination.

Matching a guest's desires to the right space, then helping them visualize it, is the interaction we want to get really, really good at.

Time back as the measure of success

At its core, Line is about giving back the most valuable thing: time. For guests, that means getting answers in minutes instead of days. For teams, it means fewer late-night replies and more space for creativity, service, and growth. That's how we are measuring success: did we give you time back, and did it help improve bookings?

Founder spotlight: Eli Hooten

I want to spotlight our co-founder and CTO, Eli Hooten. Eli and I first met nearly six years ago when he recruited me from GitLab to join Codecov. Since then, we've had the chance to build, learn, and grow through several chapters together, including Codecov's acquisition by Sentry. Line feels like a natural continuation of that journey and our partnership.

Eli earned his PhD from Vanderbilt, went through Techstars, and co-founded GameWisp and Codecov before founding Line. He also co-owns a rentals business, where he experienced firsthand the inefficiencies and daily friction that operators face, part of what inspired him to bring that same innovation and empathy to hospitality.

What stands out most about Eli isn't just his world class technical depth, but the way he leads. He has a calm, steady presence and an instinct for solving hard problems without ever losing sight of the people behind them. There's also that unmistakable Southern drawl and a sense of hospitality that comes through in how he builds and how he treats people.

It's a real privilege and honor to work alongside him, to see the innovation he's bringing to this space, and to be part of a team that shares both history and purpose. We couldn't ask for a better partner, leader, or friend to be building with.

What's next

We're continuing to train agents and onboard properties from the waitlist. Here's what we're focused on next:

• Iterating on sales finesse and the agent qualifying process
• Events calendar, tracking, and management tools
• Seamless payment and transaction layer
• Smarter knowledge layer to capture each property's nuance
• Building on "vibe of property" experience to help guests visualize their group

We regularly attend industry events like Phocuswright and IAAPA Expo. If you're going to be at one, let's connect.

– Kyle