Cali BBQ Media is a digital marketing and digital storytelling agency and studio


Hear the latest episodes


See the latest videos


Browse the latest content

How Cloudbeds is Prepared for a Digital Future and Remote Culture

DH052 Cloudbeds HQ - Screenshot - Office Tree

Cloudbeds cofounders Adam Harris and Richard Castle are maintaining their space. After all, they have plenty of it.

As they enter the Downtown San Diego headquarters for their thriving company Cloudbeds, none of the company’s 420 employees across 135 countries are currently in the 10,000 square feet space.

DH052 Cloudbeds HQ - Screenshot - Office Space with Desks

This of course, was not the plan.

“We have a 2000-square-foot patio in the back that hasn’t been used ever,” notes Adam Harris on their newly built San Diego headquarters on an episode of our Digital Hospitality podcast in September 2020. “We were all looking forward to using it during the summertime for the first time.”

When scaling that patio and the entire headquarters, one won’t currently find any employees, but they will still find kegs, ping pong tables, fake trees, arcade games and a fully loaded XBox. All currently unused.

DH052 Cloudbeds HQ - Screenshot - Ping Pong Table

Like many tech companies, Cloudbeds was intent on creating a space that provided the same fun and homey feel as their peers at other startups, as well as their clients in the hospitality industry.

Sadly, COVID-19 and 2020 had other ideas. As it did for many of us.

“This was about having fun at work and bringing out the child in us a little bit,” shares Adam Harris while touring the offices with Richard Castle and Digital Hospitality podcast host Shawn Walchef.

“We wanted a place where not only our employees felt comfortable, but also we could bring the community in to host events with other entrepreneurs.”

The fact that Cloudbeds was bringing startup culture and Silicon Valley vibes to downtown San Diego set them apart from their Cali competition.

DH052 Cloudbeds HQ - Screenshot - Office Meeting Room

Typically speaking, most programming prodigies and tech entrepreneurs congregate in Northern California in hopes of creating the next app or piece of software that changes the world and in doing so brings fortune and fame.

For Adam and Rich who both claim roots in San Diego, growing their startup in the city they call home was a meaningful differentiator from their tech brethren. Just the same, being transient, traveling, and working remote was even more so at the heart of what Cloudbeds was always about.

DH052 Cloudbeds HQ - Screenshot - BTS Recording 3

“We actually started Cloudbeds as guests, as travelers,” tells Rich Castle. “We called it Open Table for travel.”


Founding Cloudbeds:

Realizing there was a hole in the boutique hotel space, Rich and Adam devised software and systems that made booking both domestically and abroad both safer and more efficient for everyone involved.

Since starting in 2012, you could say they’ve done pretty good.

“Every second, thousands of dollars are flowing into our properties and that’s the result of our technology,” Adam states.

As alluded, the better portion of the last decade has seen things get better and better for Cloudbeds. Working with properties in 37 different countries and employing over 400 team members, the San Diego startup is integrated internationally and thus allowing clients, customers and staff to all flourish.

DH052 Cloudbeds HQ - Screenshot - Awards

The plan was to have 30 or so of those employees call the San Diego HQ home in 2020 with the rest of the team flying in and out of California as they pleased while working remotely all over the globe.

“We have a condo downtown that is available to any of our staff to use,” says Adam on their San Diego base. “We have the same thing happening in Sao Paulo, Brazil. The goal is to have twenty-five to fifty of those around the world. Just allowing our staff who all love to travel to be able to fly to one of their favorite cities and know that they have a nice place to stay in. A place that’s secure and also a great place to work. That’s part of the DNA of this culture.”


Cloudbeds DNA:

In 2020, the holistic importance of hospitality and travel is still very much a part of the Cloudbeds culture and DNA.

Because of COVID-19, plans for Cloudbeds and the world at large changed.

“We actually had an employee fly to Sao Paulo,” starts Rich. “He was supposed to stay a couple of weeks and he kind of got stuck in Brazil because of COVID. We just rented him the place there for months.”

The global pandemic has slowed travel for many and made Cloudbeds completely remote in spite of a brand-new San Diego HQ and even plans for a space in Europe.

DH052 Cloudbeds HQ - Screenshot - Walking

“We were in the process of putting an entity in Spain,” shares Rich. “It’s going to help us with hiring and recruiting staff — especially engineers. It’s a really hot place to hire in Europe.”

While the San Diego HQ is still standing and placing an entity in Spain is still in talks, all the talks amongst Cloudbeds employees now take place over Zoom.

Fortunately for Adam, Rich and the Cloudbeds team, working remote has served as a supported and even encouraged option since they started in 2012.

“The office culture is a secondary culture to the remote culture which comes first,” notes Rich. “That’s really how we were set up even before COVID.”

DH052 Cloudbeds HQ - Screenshot - Richard Castle 2

Yes, even with the investment of a 10,000-foot headquarters, Cloudbeds employees were allowed and encouraged to float all over the world. As a travel company, this proved they walked their talk. As a tech startup, this flexibility and freedom helped create a company culture that was celebrated all across their industry.

“Before we even had an office, we started getting our first awards,” says Rich on Cloudbeds’ company culture. “I think it’s making people feel engaged with the company. They have a purpose. We’ve tried to create a workplace where they feel like they’re changing travel, they’re changing the world. They’re doing something for people who love to travel and host all over the world.”

DH052 Cloudbeds HQ - Screenshot - Neon Sign Hallway

Even in the middle of a pandemic with employees working remote worldwide, the Cloudbeds team is changing travel for all involved.

In fact, some Cloudbeds properties are actually thriving despite the dire conditions.

“We’ve actually seen some really incredible brands that are nearly 100% occupied right now despite everything that’s going on,” shares Adam. “They’re running with two people because the technology at Cloudbeds is literally taking up the slack for a lower count of employees or staff, and that’s driven by technology.”

With top notch occupancy and next level technology taking care of the mundane day-to-day work, Cloudbeds clients are able to better grow their brand and serve their customers.

Staying true to the Digital Hospitality thesis and the importance of having systems, many Cloudbeds properties have been able to better write their own narrative thanks to the San Diego based company’s sleek technology and modern media.

DH052 Cloudbeds HQ - Screenshot - Talking in Office

“We’ve seen brands transform into storytelling,” notes Adam. “With their own digital brand, they’re now putting you front and center. They’re no longer sort of just showing a photo of a room. They’re putting people in the room so that you can almost visualize staying in that room because there’s less communication happening in the normal sort of scope of the world. I think that’s awesome. It’s about experience. For Rich and I, as avid travelers, want more of that.”

More storytelling and more travel are something all of us want.

On top of storytelling from boutique brands, we want check-in to be as seamless as possible. Due to safety concerns regarding the Coronavirus, many hotels are looking to adapt to the rapidly evolving times.

“If you are trying to check-in without touching anyone and go completely contactless nine out of ten properties can’t do that right now,” says Adam. “And that’s what we want to fix over time.”

DH052 Cloudbeds HQ - Screenshot - Adam Harris 2

Cloudbeds is committed to making contactless check-in a reality for the hotel industry. By leveraging their technology and tools, automation will continue to be integrated at every level of the hotel space so that owners and operators can spend more time serving their guests and telling their story.

“What I get most excited about is that our property owners no longer have to think about the day-to-day of technology,” beams Adam. “The technology is taking steps away from what they were used to. So, all those manual processes? 80% of them, we’ve automated. We’re going to continue to do more and more over time.”

The future is now for Cloudbeds, even if COVID has slowed down travel or put a pause on working out of their new San Diego Headquarters.

Nevertheless, Adam and Rich are content on growing the company by recruiting the top talent from both industries they call their own.

DH052 Cloudbeds HQ - Screenshot - Adam Harris and Richard Castle

“We love pulling people out of traditional hotel jobs and bringing them into a technology centric company,” says Adam. “Their experience is a million times better because of our culture. There’s a lot of companies across the entire landscape that are hiring and we’re one of them. We love to see resumes.”

So, are you looking to change travel and change the world? There’s not just space in the Cloudbeds office, there’s space on the Cloudbeds team.

Learn more about Cloudbeds online at

Check out the full Digital Hospitality podcast with Adam Harris and Richard Castle at Cloudbeds at CaliBBQ.Media.

Leave a Reply

Your email address will not be published. Required fields are marked *