Check in to The Upgrade, Episode 1

April 27, 2026
5 min
Contributors
Jamie Mcbride
Head of Marketing
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The Upgrade, Episode 1: a recap from the host chair

A recap from Jamie McBride, Head of Marketing at Bookboost

Last week, Jesse (our Product Director) and I hosted the first episode of our new product webinar series, The Upgrade. We had people dialling in from Madeira, Stockholm, Berlin, Barcelona, Palma, Oslo, the Netherlands, and a few places in between. A proper mix, which was lovely to see.

The idea behind the series is simple. We sit down to talk product, the why behind what we build, and all things hospitality tech. We’ll take deep dives on what we've shipped and what's coming. Honest context on the problems we're actually trying to solve, and the occasional tangent into where our space is heading, what's working, what isn't, and what it all means for the hotels we work with every day. Less fiction, more real thinking out loud.

Episode 1 focused on what Bookboost has been up to in the first quarter of 2026 and covered four areas: guest conversations, guest data, insights, and connectivity. Here's the recap with a few of my own notes from the host chair.

🎥 Prefer to watch the full session? Catch it on demand here.

1. Guest conversations: our AI agent

The scene-setter here is something most hoteliers will recognise instantly. Your front desk and reservations team spend hours every day answering the same handful of questions. Check-in time, parking, Wi-Fi, breakfast hours. Across WhatsApp, email, SMS, OTA messaging.

That isn't really a technology problem. It's a time problem. Your team's expertise is being spent on repetition instead of hospitality.

What we've shipped: the Bookboost AI agent, live inside our unified inbox.

A few things worth calling out:

  • It reads and responds using knowledge you configure. No hallucinating, no going off-brand.
  • It works natively across WhatsApp, SMS, email, and Expedia.
  • Multi-language out of the box, so your guests are answered in their own language on their preferred channel.
  • Draft mode is there if you want AI assistance but still want humans approving every send.
  • Built European-first, with the guardrails you'd expect from a GDPR-native platform.

Jesse dropped a teaser at the end of this section that I'm quite excited about. The agent today is a helpful, passive question answerer. The next version becomes an agent of action. Housekeeping requests that create tasks for someone on the ground. Upsell conversations that actually execute. That's where this starts to feel less like a feature and more like a teammate.

2. Guest data: master profiles

This is the one Jesse nearly ran away with, and I understand why.

Guest data in hospitality lives in five, six, sometimes a dozen systems. PMS, channel manager, booking engine, email platform, review tools, spa and F&B systems. You cannot personalise, you cannot automate, and you certainly cannot point an AI agent at any of it until that data is unified.

What we shipped: our match-and-relate algorithm, and master profiles inside the Bookboost CRM.

The key detail that gets missed in every "unified profile" pitch you've ever heard: it's non-destructive. We cluster profiles from your source systems into one view per human, but we keep the source context underneath. You're not losing nuance. You're gaining a layer on top. And because it's all handled inside a European-native CDP, the data residency and consent side stays clean by default.

Reservations, form submissions, campaigns received, inbox tickets, all in one place, tied to one guest. It's the bedrock for everything else we've shipped, and everything we're shipping next.

3. Bookboost Insights

Before we got into this section, I ran a quick poll: "How are you reporting on guest engagement today?"

Around 40% of the room told us they aren't looking at it at all. The rest were split between spreadsheets and PMS reports, with a handful on a proper BI tool.

No judgement. That is the state of our space, and it's exactly the problem Bookboost Insights is built to solve.

Insights is built on two ideas:

  1. Reporting on guest data should not require a data team or an expensive BI tool.
  2. You should be able to ask questions in plain English and get real answers back.

So Insights has an AI agent built natively into it. Ask a question, it builds the dashboard. Build fully custom dashboards for your hotel's specific questions. Use templated dashboards if you want a starting point. Schedule reports out to stakeholders every Monday at 9am so your GMs actually know what's happening with marketing for their property. Export in the formats you need.

And if you already have Power BI or Tableau, Insights will feed them too. The master profile and reporting data will be available via our public API and webhooks, so Bookboost doesn't become another silo.

We're in early access on this right now, and I'd genuinely love to get more hoteliers into the early cohort. If you're an existing customer, request early access here and we'll get in touch.

4. Connectivity: the quickfire round

Your tech stack is not getting simpler, and neither is ours. A few highlights from Q1:

  • Opera Cloud: now a full two-way integration. The digital journey you run in Bookboost contributes data back to Opera.
  • Guestline: new PMS integration, two-way, first customers already live. Particularly good news for the UK and Ireland market. (Which, I'll admit, made me personally happy.)
  • Unified inbox routing: per-property assignment for groups managing multiple teams.
  • Recurring broadcasts: finally. Birthday messages as a one-click action, not 365 separate sends.
  • Form-based segmentation: turn form submissions, including review feedback, into audiences automatically. Negative review? Route to a save-flow. Positive review? Route to a loyalty ask.

Coming next on connectivity: Protel Cloud, master profiles exposed via our public API, tighter integration of master profiles into segmentation and campaign building, and a new version of the CDP API with expanded endpoints (master profiles, segmentation, reviews, and more).

Less glamorous than a new AI feature, but this is the scaffolding that makes everything else move faster.

The questions you asked

The Q&A was one of my favourite parts of the session. A few of the questions worth pulling out here.

"We use Opera Cloud. Will master profiles sync back into it?"

Not today, and we're not promising a specific date yet. What we are actively exploring is something more flexible: a browser extension layer that puts master profile data on top of Opera Cloud, or a spa system, or a table-booking tool, or anywhere else your team works, without waiting for each vendor to build a native integration.

The ambition is for master profiles to be useful everywhere, not just inside Bookboost. I don't think any other hospitality CDP is thinking about the problem that way, and that's probably the clearest signal of where we're pointed.

"Hotels have had this problem forever. What's actually stopping us fixing it once and for all?"

This was my favourite question of the session, and I think about it a lot. Jesse's answer was a mix of trust and capability.

Trust, because AI has been taboo in hospitality for a long time, and the past 36 months have quietly shifted that. AI has inserted itself into our workflows whether we thought about it consciously or not.

Capability, because chatbots could only ever answer questions a human could have answered. The new generation of agents takes action. That's the paradigm shift, and that's where adoption really starts to move.

And honestly? I agree with him. Our space is about to cross a line from "AI as a faster FAQ" to "AI as a teammate." That's the real unlock.

"How does the AI agent work across multiple properties?"

You can have one agent, or many. Route by property, by channel, by email domain, by whatever routing rule you already use in the unified inbox.

Each agent has its own knowledge base. We're making it easier to share core knowledge across agents while keeping the property-specific bits local. Designed to scale from one property to fifty-plus.

"Can the AI agent have its own tone of voice?"

Yes. Custom tones and custom prompts. Greet guests a specific way, sign off a specific way, reflect a specific brand personality. It's configurable, and it's one of the small things that tends to separate a guest thinking "that was a bot" from a guest thinking "that was our hotel." We know which one you want.

Why this matters

Everything we shipped this quarter points in the same direction. Your guest data belongs to you, not to the OTAs. Your guest conversations should be easy, fast, and on your guest's channel of choice. Your reporting should answer real questions, not bury them in dashboards. And all of it should be built by people who understand data protection and security is not a bolt-on.

That's the ground we're building on, and it's the ground most of our customers picked us for.

What's next

Episode 2 is coming next month, and we've already got some fantastic topics lined up for future sessions. If you have any feedback or if there is anything in particular you would like to see us cover, drop us a note here.

If you're new to Bookboost and any of this resonates, book a demo and we'll walk you through the AI agent, master profiles, and Insights in context rather than in the abstract.

If you're already a customer and you want into the Insights early-access cohort, or you're interested in learning more about it sign up here.

And to everyone who joined, asked a question, or dropped a hello in the chat, thank you. These sessions only work when there's a room on the other side.

See you soon for Episode 2.

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