Building Line: software for guests and teams

From the age of 15, I worked in nearly every hospitality role you can imagine: housekeeping, front desk, bartending, night audit, catering coordination, sales, and conference services. I worked in mom-and-pop venues, catering-only businesses, and global hotel brands like Kimpton, across places like San Diego, Vail, and Washington D.C. These experiences taught me that hospitality is about how you show up, lead, and serve guests with deep care. And while that was my day job, at night I was teaching myself design and how to build websites...

Later, I transitioned into tech and I've been building software nearly a decade and half with organizations of all sizes and capacities: client work in fin-tech, dev tools like GitLab, to early-stage startups. During this time, I learned the power of building systems that scale, solving deep user and technical problems, and how innovation comes one small experimental iteration at a time.

Now I'm coming full circle: combining those two worlds to help fix what's broken in hospitality today. Along the way, I kept hearing the same frustrations:

"I'm so tired of this every weekend I come to work to do all the computer stuff."

– Conference Services Manager

"Instant attention is everything now with these young people. If they don't hear back in a minute, they freak out. I still block off dates manually in Google Calendar."

– Owner, Event Venue

"I wish there was something to clean up our emails – my team is totally bogged down. Our setup sucks and I hate Salesforce."

– Director of Sales

"The top concern every year at the GM's meeting was how broken the sales workflow was (groups, meetings, and events)."

– GM

"From inquiry to invoice, our workflow is super manual. The biggest issue is inventory management."

– Owner, Rentals Company

I know what it's like to sell and then run an event with a skeleton crew. I've stayed up all night fixing last-minute banquet orders. I've wrestled with endless email threads, broken CRM setups, and customers who never received the information they needed. I've heard hundreds of stories just like mine.

But I've also been on the other side – the customer who fills out a form and never hears back. Who gets a generic copy-paste email with a PDF attachment, sometimes even addressed to the wrong name, like 'John', because it was copied from the last email they sent. Who calls in the evenings or weekends, when they finally have time, and no one answers. The experience is broken on both sides. And no matter the size or type of venue, the stories always sound the same.

That's why I'm building Line – to bring hospitality to the full experience, not just the moment a guest arrives. I believe the guest experience starts at the first click, and it should feel as welcoming, responsive, and thoughtful as check-in. At the same time, I want to make life easier for the teams who make these events happen. Line is here to serve both sides of that equation – the guest and the staff – with tools that reflect the spirit of great hospitality from start to finish.

Why Now?

Today's customers expect fast, clear, and thoughtful responses, yet most hospitality teams are stretched thin, buried under outdated workflows and clunky tools.

You've probably experienced it yourself:

• Inquiries get lost in inboxes
• Staff spend hours rewriting the same emails or digging up the same PDFs
• Guests bounce between email, calendar, and payment platforms never sure who's handling what

And on your side? You're juggling proposals, availability, inventory, and guest expectations, often without the right systems in place. It's not just stressful, it's unsustainable. And to be really honest, not hospitable!

What Line Does

Line is an AI-powered assistant built specifically for hospitality teams.

Think of it as an always-on, highly trained helper that knows your business and can assist with:

• Responding to inquiries with personalized, on-brand messaging
• Sharing availability and relevant photos or videos
• Drafting proposals and following up automatically
• Helping you close more business – faster

For your team, Line saves time and makes your life easier. For your guests, Line offers the warm, professional service they expect: instant hospitality. We believe the inquiry experience is the guest experience. So we're starting there.

Who It's For

Line is for any hospitality business that handles private events, rentals, or group sales. Line is building out integrations to work alongside the tools you're already using, not to replace them. We're not building cold automation. We're building warm, AI powered responsive tools that help you show up better for your guests.

Our Promise

At Line, we aim to be unreasonably hospitable. Not just in how we serve your guests, but in how we serve you. Our goal is to bring the same level of care and professionalism to your sales process that your team brings to every event. We're starting with: an embedded assistant for inquiries, paired with a manager dashboard that helps you respond, schedule, and close.

From there, we're building a complete solution that handles everything from inquiry to invoice. One seamless workflow that ensures your guests feel taken care of at every step - whether they're browsing your website, planning their event, or experiencing it at your property.

Let's Build the Future of Hospitality Together

If you're tired of duct-taping tools together or losing business due to delays, I'd love to show you what we're building. We're rolling out with a handful of early adopters and actively iterating on the product with them. If that sounds like something you want to be part of, I'd love to talk.

Thanks for reading – how may I be of service? Let me know at kyle@withline.io

– Kyle

Guest experience starts at check-in the first click

If you're in the hospitality business - whether you're running a boutique hotel, a wedding venue, a rental company, or an event space - you already know how important it is to deliver exceptional service once a guest arrives. Beautiful spaces, warm greetings, and attention to detail are table stakes.

But the thing is: for your guests, the experience doesn't begin at check-in. It begins with the first click. Look around the industry and it's clear - that same warm, high-touch hospitality that defines your property often disappears online. Instead, guests are met with outdated websites, confusing layouts, and a generic form at the end of a long scroll.

What should be an exciting moment - envisioning and planning an event - turns into frustration. You click around, hoping for inspiration or clarity, and instead land here:

A cold, impersonal form. It's something you fill out not because you want to, but because it's your only option. And if you decide to call instead? Either you're playing phone tag or yelling "agent!" at a phone tree. Or worse, interacting with a chatbot that's not built to help.

This experience isn't just inconvenient - it's the opposite of hospitality.

Consider this recent experience: I tried to submit a group meeting request at the local IHG-Kimpton Armory Hotel. I couldn't complete the form. I called, but it was the weekend, so no one was available. When I finally connected with someone the following week, I explained how hard it was to get in touch. The Director of Sales told me, "well, all places are like that, sales offices work 9 to 5". And about the website, "well, you need to contact IHG".

And the director isn't wrong - I've been there. But what's missing is that the staff all too often is working nights and weekends just to stay afloat. And still, they can't keep up. That mindset of "that's just how it is" isn't just disheartening - it's the enemy of hospitality and innovation. All told, guests are frustrated, staff are exhausted, and opportunities slip away.

This is the unfortunate reality in hospitality today. And it's a problem I'm determined to solve.

It Starts Before They Walk In

Guests expect clarity and responsiveness from the moment they hit your website. And yet, most hospitality businesses fall short:

• Vague contact forms
• No visibility into availability or pricing
• Delayed or missing responses
• Confusing back-and-forth over email

That first interaction sets expectations: Can I trust this team? Will they respond quickly? Do they care? And if the experience feels impersonal or slow, the guest moves on.

Line has created a solution that helps your customers upon inquiry and provide instant feedback, questions, and tailor made visuals to help them kick off the experience.

Serving Back of the House, Too

Outdated tools, manual processes, and siloed systems don't just create stress - they cost bookings.

"My team is buried in emails and can't keep up."

"Guests want fast answers, and we can't keep up."

"We miss leads all the time."

We built Line to fix that. Our assistant connects to your tools, learns your spaces, and helps you respond faster. That means less chasing emails and more time actually serving your guests.

Let's Raise the Bar

Your online experience is your brand. It's time we treated it with the same care we give the lobby, the room, or the reception hall. If you're ready to deliver hospitality from the first click - not just from check-in - we're building Line for you.

If this resonates, let's talk. We're working with partners who are ready to raise the bar, for their guests and their teams. How may I be of service?

Reach out: kyle@withline.io

How Line revolutionizes the booking process

As an event company owner, I've navigated countless back-and-forth conversations with venue sales associates, often feeling bogged down by the sheer amount of communication required to get everything just right. My events come with specific requirements—a patio that's fully fenced, dog-friendly policies, a certain price point, and ideally some roof coverage. While these details ensure a seamless experience for my clients, hashing them out often feels tedious and inefficient.

This inefficiency doesn't just impact me; it affects the sales associates too. I've seen firsthand how the endless emails, phone calls, and potential miscommunications can leave staff drained, making them less present and less effective when the event day arrives. The back-and-forth takes a toll on everyone involved, and the risk of unmet expectations can create unnecessary stress.

That's why I was so eager to help develop and advocate for Line, a platform that's transforming how venues and customers communicate. Imagine being able to review a venue's Instagram profile or website, then seamlessly initiate a conversation through Line, getting real-time answers to all your questions. With Line, I can confirm key details about roof coverage, fencing, and dog-friendly policies without ever feeling like I'm going in circles. By the time I'm ready to book, I have complete confidence that my expectations are clear and will be met.

For event owners like me, Line solves some of the most persistent challenges:

• Real-Time Communication: No more waiting hours or days for replies. Line's instant messaging ensures you get the answers you need when you need them.
• Streamlined Communication: Reducing the risk of miscommunication and mistakes.
• Enhanced Staff Presence: With less time spent on pre-event logistics, sales associates and venue staff can focus on delivering an exceptional experience during the event itself.

What makes Line truly stand out is its ability to minimize human error. Traditional chatbots often fall short, offering limited responses that can't progress an inquiry meaningfully. On the other hand, Line combines advanced automation with real-time human support when needed, ensuring that nothing falls through the cracks.

As an event company owner, I know how critical it is to work with venues that value efficiency and professionalism. That's why I'm now using my experience and passion to help venues adopt Line. By integrating this platform, venues not only improve their booking process but also demonstrate to customers that they're committed to providing a premium experience. Early adopters of Line are already seeing the benefits: faster sales cycles, happier clients, and a competitive edge in the market.

In the fast-paced world of event planning, tools like Line aren't just helpful—they're essential. For any venue looking to enhance its operations and attract more bookings, the choice is clear: streamline your process, embrace innovation, and show your customers that you care.

If you're ready to transform your venue's booking experience, let's connect. Together, we can make tedious communication a thing of the past and create a future where event planning is as seamless as it's meant to be.

Reach out: sylvia@withline.io

Building for the golden age of in-real-life experiences

There's no shortage of noise around AI: dramatic headlines, dire predictions, and endless hot takes. But while that noise plays out, we're focused on building: technology powered by AI that can actually help event and hospitality teams get back to doing what they do best.

Hospitality is about presence. It's about creating moments that feel personal and memorable. It's why so many people chose this profession in the first place: to host, to connect, to make someone's day.

But somewhere along the way, teams got stuck juggling clunky websites and repetitive admin, while dealing with staffing shortages and growing guest expectations. Instead of spending time with guests, they're fighting with their tools.

We believe innovating the workflows with LLMs is an opportunity to change that. Not by replacing people, but by freeing them:

• By automating the repetitive
• By giving guests answers on demand
• By creating systems that support your team and not slow them down

One restauranteur put it simply:

"I'd love to get this email and booking stuff off my plate, and back to innovating my menus and events for my guests."

Exactly. That's our vision.

At Line, we're building tools that serve your staff the same way your staff serves your guests. Tools that quietly remove the friction, so your team can be more present, more responsive, and more focused on what matters most: the guest experience.

Because here's what we see: travel is booming and people are craving real-life connection. Hospitality is the industry that can deliver it, but only if we give teams the support they need. This is the golden age of hospitality and it's time the tools caught up.

If you're building for this future too or if you're just tired of being held back by outdated systems – we'd love to talk.

Let's build together. Let me know how we can help: kyle@withline.io

Hospitality for employees

Lately, I've been visiting venues, museums, and hotels and talking with operators. Walking into these properties, you're immediately struck by the design, ambiance, and attention to detail. When it's done right, it doesn't just feel like a welcome home, it feels like wow, I get to hang here 😎.

Then, I get ushered into the back office. Anyone who's worked in hospitality knows the contrast. The back of the house is often the complete opposite of the guest-facing side: cluttered, dated, and stressful. That's not something Line can fix physically. But what we can do is bring hospitality to your staff's workflows (and guest).

Line is building an experience that treats your team with the same thoughtfulness and service that you extend to your guests. Our interface says, "How may I assist you?". Why shouldn't your staff experience the same level of care you aim to deliver on property?

In nearly every conversation I've had, the post-COVID challenges are clear:

"We used to run with 14 staff, now it's 5, and we have double the demand."

"We can't find talent. Many have left the industry entirely."

"My team is exhausted. They're drowning in busywork."

There's something wrong when one of the most service-oriented industries is stuck with some of the clunkiest, most unfriendly tools out there. We believe great hospitality starts with the people behind it and they deserve better systems!

If this resonates, let's talk. We're working with partners who are ready to raise the bar, for their guests and their teams. How may I be of service?

Line newsletter #1

👋 Dear friends,

I've been talking with hundreds of hospitality folks: sales leaders, GMs, chefs, restaurateurs, asset managers, owners, you name it. It's been both inspiring and eye-opening to hear about your workflows, pain points, and ideas for the future.

And beyond the conversations, I want to thank our early adopters, the hotels and venues in the U.S. and Europe partnering to bring Line into practice. You're not just "trying software", you're helping prove what is possible while shaping the next chapter of innovation in hospitality.

Our promise: we'll be working around the clock to smooth out the friction points you and your guests feel every day so your teams win back time, get your property AI ready, and more inquiries convert into real business.

Introducing our new pilot: hotel AI reservations agent

We're piloting our AI reservations agent, built to meet guests wherever they discover you: social, maps, AI search, or messaging. No more clunky websites, endless forms, or waiting on calls and replies. Guests can get answers and book instantly at the moment of discovery.

For properties, that means more direct bookings, fewer missed opportunities, and a smoother guest experience from the very first click. And this is just the start: it builds on the foundation of a single AI sales agent that also handles customer service questions and qualifies group sales leads. Interested? Shoot me an email or DM.

Spotlight: Line's Co-Founder Katia

Katia is Line's co-founder and COO, based in Toronto. We've been building together for years: first at Codecov, then through the Sentry acquisition, and now at Line. From deep engineering to leadership, she's built AI agents that resolve software bugs and now building agents that sell, drive bookings, and close business 24/7.

The spark for Line came when she was searching for a venue with her partner and ran into the same bottlenecks and frustrations she's heard from staff time and again. That "aha" moment made it clear: hospitality deserved better tools.

I couldn't be happier to be on this journey with Katia. Her mix of discipline, empathy, and technical depth is exactly what it takes to reimagine hospitality technology with the customer experience at the center. Reach Katia at katia@withline.io or connect on LinkedIn.

October ahead

We'll be training our agents, working closely with design partners, and connecting with more customers to learn from their workflows. Our goal this month: make our first deployment...the world's first AI agent for group sales. We'll also be at The Hospitality Show if you're there, let's connect.

We're just getting started, and I can't wait to share what's next.

Kyle

The new white pages are coming

As a kid, National Geographic magazines were my window to the world, filled with exotic destinations and hotel ads tucked between the pages. Reflecting on it now, it's remarkable how much discovery has evolved in such a short time, moving from print to web to mobile. Now it's shifting again: across social feeds and into AI interfaces.

Today, in a major leap, OpenAI launched Expedia and Booking.com apps inside ChatGPT, letting users search, compare, and book hotels directly in the interface.

At first glance, it may seem like another win for OTAs. But look closer and there's a shift underway, one that could actually strengthen the guest experience and return control of distribution to properties.

A Brief history of discovery

And to understand where we're headed, it's worth looking back.

The white pages era

For decades, the white pages were the map of the world. If you weren't listed, you didn't exist. Guests might stumble on you in a directory, a glossy magazine, or a brochure from a travel agent. Discovery was limited, but at least it was structured and centralized.

The fax & phone era

Once they found you, booking meant a long-distance call or even faxing over credit card details. It was clunky, slow, and often expensive but it gave hotels something valuable: a direct line to their guests.

The web era

In the late '90s and early 2000s, the web became the new white pages. A destination in Wyoming could suddenly be discovered by a family in Tokyo. Websites, email, and inquiry forms replaced long-distance calls. They were cheaper and asynchronous, and they quickly became the backbone of RFPs, group inquiries, and confirmations. The workflows of forms, attachments, and endless email chains were born here.

The OTA era

Then came the rise of Online Travel Agencies (OTAs) and Google Maps. Discovery no longer started with your name, it started with a search box. Guests typed in a city, and OTAs controlled the results. OTAs delivered massive visibility, but at a cost: steep commissions, brand dilution, and a lost direct relationship with the guest.

Today's discovery opportunity

And today: guests are asking conversational questions inside AI-native platforms like ChatGPT, Gemini, and Perplexity:

"What's the best boutique hotel in Austin for a small team retreat?"

"Find me a romantic getaway within three hours of Chicago with a spa."

"Where should I book our company retreat for 200 people in San Diego this fall?"

Add to that the rise of social discovery: reels, travel creators, and friends' recommendations.

• In 2022, only 4% of Skift Travel 200 companies mentioned AI. By 2024, that jumped to 35%. (McKinsey + Skift)
• 90% of travel managers now use AI tools, and 73% use them specifically to streamline booking (Business Travel News)
• 57% of travelers say they're comfortable booking high-priced activities directly through social media (Skift)

From social feeds to AI assistants, guests are finding and booking in entirely new ways. The question is: is your property ready?

Improve distribution and get AI-ready

You can take concrete steps now to position your property ahead of the curve and make it discoverable in this new landscape.

Step 1: remove communication blockers

Many properties still rely on static inquiry forms. But if a guest's AI assistant encounters only a form, that is a dead end. Assistants need real-time answers.

Start by deploying an AI sales agent on your site and across your channels. Think of it as a digital team member that is always on, able to answer questions, qualify leads, and move guests toward booking.

This is actionable today, here's hospitality at first click: guests can discover a property and instantly engage with an AI agent that answers questions, provides availability, and completes direct booking all in one seamless conversation.

Step 2: Prepare for AI-native search

In Step 1, you set the foundation, your data and AI sales agent are ready to engage guests directly. The next step is making that same capability visible inside AI platforms.

So the question becomes: how can your property increase direct bookings and build a direct workflow that appears there?

The most likely bridge is something called the Model Context Protocol (MCP), the developer standard that helps AI systems understand and communicate with data you have (availability, rates, event spaces) and connect you directly.

What is an MCP

Think of the Model Context Protocol (MCP) as the new white pages for the AI era: a digital listing that tells AI systems who you are, what you offer, and how to reach you.

In simple terms, MCP is a technical standard that makes your property's data readable and accessible to AI. It acts as a bridge between your systems and platforms like ChatGPT, Gemini, or Perplexity.

Once it becomes a standard, properties without MCP may only appear through OTAs or generic listings when a guest's AI assistant looks for hotels. With MCP, your property becomes visible, discoverable, and bookable directly inside the conversation.

MCP adoption is still developing, and no one can predict exactly how it will evolve. But deploying an AI sales agent today puts your property in the ideal position to activate MCP the moment it becomes the standard.

AI readiness

If you prepare now, the benefits could be profound:

• Meet guests where they are: AI assistants, social discovery, or on your own site.
• Deliver a better experience from the first interaction, with instant, intelligent responses.
• Regain control of bookings bypassing OTA commissions and restrictions.

The AI-native wave is your chance to rewrite the story and take back your distribution.

At Line, we're helping properties get AI-ready today from deploying always-on sales agents to preparing MCP endpoints that make your property discoverable in AI-native channels.

Are you AI-ready? I'd be happy to help, email me at kyle@withline.io

Part I: a problem worth solving

My co-founders and I all quit our jobs determined to solve this problem. And truthfully, there has to be something wrong with people who do this. We traded healthy, seemingly safe salaries and stability for a journey that includes failure, rejection, and isolation in order to bring something new to market.

So, naturally, the question is why do it? Simply: because it's a problem worth solving.

In this two part post, I'd like to examine the problem, the people involved, the market, and why this category is overdue for innovation.

The nature of this problem

Problems come in different forms. Some are known knowns (waiting in line), some are known unknowns (diseases) and some are unknown unknowns (the deeper questions of the universe and life that we can't imagine). And then there's another category: the problems thinly disguised as "conventions", let's call it the known-but-it's-convention-so-oh-well-known, it goes something like this:

We know it's broken.
They know it's broken.
They know that we know it's broken.
We know, that they know, that we know, it's broken.
And yet, the charade carries on.

When you see this pattern, make note. It's a deeply rooted problem. Group sales in hospitality is one such case.

The people involved

Let's peel the onion, starting with the most important part: the people.

Group business means weddings, conventions, corporate events, retreats, meetups, amusement park groups, and anything involving a private group space or for hotels 9+ or more rooms. Two sides:

• The customer
• The property

Let's consider their goals, motivations and experience navigating this space.

The guest experience

When a guest starts planning a group, they're trying to identify:

• Pricing
• Availability
• Vibes (does this place feel right?)

To get those answers, they're dragged through a maze of scrolling, dropdowns, PDFs, calling, emailing, forms, and hoping someone gets back to them. Hours spent with no clarity on pricing or availability and some vibes from the website, Instagram, or Google Maps.

Eventually, all this investigative work leads them to stitch together a DIY "marketplace." It takes days, weeks, sometimes months. And all they wanted were three things: price, dates, and vibes.

What's crazy is they might have a $50k piece of business, a totally normal group spend, and this is still the "first click" experience 🫠.

The property's experience

On the other side of this, turns out properties are focused on the same three things:

• Pricing
• Availability
• Vibes (is this group going to be great or a nightmare)

Without open market dynamics, pricing becomes guesswork. So many venue owners say some version of:

"I struggle with what to charge so I just compare it to last season."

Take note: they are looking at data that is not market data, it is just their own property last season. But because the market is hidden behind webs of emails and web forms, that is all they have. Imagine if airlines or any other business only looked at their own past flights and never at competitor or market pricing. Would this make for optimized revenue management?

If you talk to hotels you hear the same theme:

Sales:

"I email revenue management and wait for a rate"

Meanwhile, the guest is talking to ten other places 😬.

Revenue management:

"I look at the convention calendar, our previous rates, ADR, and maybe <insert legacy system we pay tons of money for>, but to be honest nobody really uses it."

The shared problem

Both sides have the same goals in discovery: pricing, availability, and vibes. The problem is the friction between them.

With no open market or transparent supply and demand signals, pricing becomes guesswork. Both sides end up overpaying or undercharging without even knowing it. Availability turns into a long back-and-forth because nothing is connected in real time. And vibes only really come together at the site visit; everything before that is forms, emails, and vague details.

The matchmaking is where the majority of friction sits.

The market

The current state

Group business is a 1 trillion dollar market. To get a sense of its impact, consider that Marriott's CEO reported that 24% room nights came from group business, roughly double their OTA bookings.

And yet, in 2025, two surprising truths remain:

• There is no group OTA or transparent marketplace
• You cannot instantly book 9 or more rooms

To me, this is wild. First, the barriers customers go through just to give properties money are staggering. And second, Expedia (~$30 billion), Airbnb (~$70 billion), and Booking (~$160 billion) are thriving in individual travel, yet there is still no true group OTA or marketplace dynamics driven by transparent supply and demand. It remains a hidden market living inside emails, forms, RFPs, and legacy systems.

The tools that do exist are not introducing market dynamics. They either double down on the RFP convention for properties (proposal builders, workflow tools, templates) or they are aggregated listings that look like a marketplace at first glance. In those listings you browse, express interest, and the system fills out forms on your behalf before returning results in a tidy UI. It is a step above the DIY process described earlier, but still not an open market.

And when you look at OTAs and listings in general, it is worth asking why guests increasingly go to Expedia, Booking, and Airbnb. It is because these platforms give them something direct channels do not: the dynamics and information of an open marketplace. Transparency, filters, instant pricing, and side-by-side comparisons. It is supply and demand working the way people expect today.

Innovation by way of transparent market dynamics

Here is a parallel analogy: we know the Uber and Lyft solution, but what was the actual problem?

Consider the cab experience before them. Everything came down to manually parsing pricing, availability, and vibes between two parties. As a customer you had to figure out which cab was available, flag them down, hope they stopped, then deal with bargaining that might be honored, ignored, or complicated by a "broken" meter. Drivers had their own issues like getting stiffed or wasting gas hunting down customers. And on both sides there were trust and safety concerns.

Then Uber came along. The core breakthrough was not the technology. The innovation was introducing transparent market dynamics to both parties. Suddenly both sides could see pricing, availability, and vibes through reviews in real time.

note: our customer today is the property. We are not building a group OTA now. We are solving the property-side problems of on-demand sales, pricing, availability, and qualification. If an open market for groups ever becomes possible, it will emerge from solving this foundational issue first.

Themes, patterns of and guest expectations

All of this is happening while demand for IRL experiences keeps rising. Ari Emanuel, CEO of Endeavor, is making huge bets on IRL entertainment. Airbnb is betting on the same trend with Experiences, and Booking.com continues to exceed expectations. These are only a few examples, but the pattern is clear: demand for real-world experiences keeps growing.

And while demand increases, customer expectations have never been higher. People have become accustomed to better design and higher quality tools at work and in everyday life. But when they try to plan a group, they fall back into 2007-era workflows: attachments, forms, PDFs, and email chains. This is the level of hospitality guests are met with at first click 😕.

Solution foundation

All of this sets the stage for where we begin. We are starting where the friction is worst: on-demand sales matchmaking between guests and properties, with the goal of saving time for both sides and helping properties win more of the right business.

So far, we've built Line to structure a property's knowledge so an agent can understand how the property wants to engage with guests and organize incoming inquiries clearly.

In Part II, I will cover why this problem hasn't been solved, what inspires our determination, and the path forward.

Line newsletter #2: awakening a better way

It's been a heads down month of building, but I did make 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.

Reflections on building with AI

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 whitepages blog.

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'll also be at Phocuswright and IAAPA Expo this month. If you're attending, let's connect.

Thanks for reading and for being part of this journey.

– Kyle