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I didn’t plan to start a company, I was trying to book a team offsite

I didn’t plan to start a company, I was trying to book a team offsite

I didn’t plan to start a company, I was trying to book a team offsite

I’ve always been a builder. Before graduating high school, I was already an entrepreneur, organising massive LAN parties with thousands of gamers and building the tournament software behind them. After graduating, I worked for myself in the events world, building my own profile and business from scratch, always with new ideas and initiatives in mind.

Joining Expedia in 2011 was the anomaly. It was a big enterprise move, but I was hired because I didn’t think or operate like an enterprise lifer. My manager saw entrepreneurial energy, a bias to action, momentum, and a desire to build, not just push paper or spend my days ricocheting between meetings.

Travel was my world. I spent years working on large-scale systems where flights, hotels, pricing, and distribution were relentlessly optimised. Booking travel for consumers and business travellers had become fast and efficient. I assumed arranging a small offsite would be straightforward.

It wasn’t.

What followed was a familiar modern frustration: long stretches of emails, slow replies, and proposals arriving after decisions had already been made. Some hotels didn’t reply at all. As someone trying to get a simple job done, it was infuriating. What remained with me was the revelation about how the work was happening on the other side and the impact of that on these venues – lost revenue, burnt out teams, and missed opportunities.

Meetings and group bookings can account for a significant share of a hotel’s revenue, yet the way they are handled has barely changed in decades. Speed matters enormously in this space, and yet delay had somehow become normal.

I raised it internally at Expedia and made the business case to leadership that this was worth exploring. It was a rapidly growing industry, expected to be $750 million globally by 2030, and it was ripe for disruption and automation. That conversation turned out to be the beginning of something much larger.

The kind of problems that get left behind

Meetings and group bookings are complex. Pricing depends on availability, contracts, seasonality and venue constraints. No two enquiries look the same and because of that, the work had remained largely manual.

This is where many valuable problems get stuck. They cut across teams and systems. They are operational rather than flashy and they take time to properly understand.

At Expedia, we began exploring automation in this area and quickly saw how much speed impacted outcomes. Every hotel or venue visit showed me sales teams were spending large parts of their day on admin that did not move deals forward. Momentum was being lost before conversations even started.

That experience shaped how I later thought about building a company.

Starting hivr.ai from what I had seen up close

When I co-founded hivr.ai, I kept returning to very specific moments I had witnessed inside hotel sales teams. Inboxes filling faster than they could be cleared, pricing being checked and rechecked and enquiries stalling while someone waited for confirmation from another system or another department. Some teams were still relying on handwritten diaries to map potential bookings!

We began by mapping where time was being lost and asking how those steps could be shortened or removed. Significant amounts of time was being spent on email enquiries, availability checks, pricing logic, proposal creation, and follow-ups. The aim was to make it easier for teams to respond while the customer was still engaged.

Trust was an early hurdle. Hospitality teams are cautious when technology touches revenue and client relationships, and rightly so. We learned quickly that broad claims were unhelpful. What mattered was showing, in detail, how the system worked and what changed as a result.

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Working with early adopters, hotels and chains like Radisson Hotel Group, and Minor Hotels who were willing to experiment and test, was crucial. What we delivered was faster response times, fewer hours spent on manual tasks and higher conversion rates. When teams could see the impact in their own day-to-day work, confidence followed.

Today we are the most connected meetings and groups sales automation platform in the ecosystem, working with global and regional hotel chains and venues; meeting and group channels such as meetago, Cvent, and Venue Directory; as well as sales and catering systems like Backyou and Ivvy – just to name a few.

What enterprise experience helped with, and what it didn’t

My time in enterprise sharpened instincts I already had. It gave me deep respect for complexity and for how many stakeholders sit behind simple workflows. But the builder in me was restless. Enterprise taught me how systems scale, but it didn’t change the fact that I was drawn to building things from scratch. From 0 to 1.

Starting a company involves constant trade-offs. There is always more you could build than you have the capacity to deliver. Learning to prioritise, and to say no, becomes a daily discipline rather than a strategic exercise.

If I were giving advice to someone thinking about starting a company, I would keep it simple. Spend more time with the problem than with the solution. Pay attention to the frustrations people quietly work around because those are often the most valuable ones.

hivr.ai came from a small, annoying experience that would have been easy to dismiss. Looking back, that offsite booking was not itself important. What mattered was noticing the friction, asking why it happened, and staying curious long enough to follow the thread.

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