In-Person Company Retreat for Remote Teams: How Heights Platform Did it

October 2022 saw the first official Heights Platform team meetup take place.

Heights Platform is an online course creation software, and its team works remotely from different parts of the world! We have team members working in the US, Europe, and Asia.

The company was founded in 2009 as a design studio, and Heights as a product launched in 2018: Today, Heights has grown significantly, and its team members have worked side by side (virtually) for years. With travel restrictions lifted after the events of 2020, 2022 seemed like the perfect time for everyone to meet in person!

In this article, we will share the highlights of the Heights Team Retreat!

This can be helpful if you are planning your own team retreat or meetup, whether you own a company with 100s of employees or you are running a small startup with a couple of people.

It can also be helpful if you are planning to apply for a job at Heights Platform, to understand more about our culture and get a closer look into the company's work-life.

Before Leaving: Planning the Company Retreat

The most important part when it comes to organizing a successful team retreat is the planning stage.

If you are the company's owner, or you are the person in charge of planning the company retreat, this task is going to be your responsibility.

Choosing the Dates

First of all, you should think about the dates of your company retreat.

In the case of Heights Platform's team trip, we started thinking about it a year in advance, and decided on a date range about 8 months before the trip.

Depending on the size of your team, the planning stage will be longer or shorter, but it is generally better to allow plenty of time for everyone to make space in their calendar and ensure that most team members will be able to join.

In our case, we finalized the exact dates about two months before the actual trip, though we were aware of the month during which the retreat was planned to occur for much longer.

Choosing the Location

Once you have a general idea of when the team trip will happen, you can start to think about where to go. This depends on many factors: is your company fully remote? Where are your team members located? How easy is it for them to get to the chosen location? Who will bear the traveling costs? What are the preferences of your team members?

For the Heights Platform team retreat, we chose Austin, Texas, as the trip's location.

There are many reasons behind the choice of Austin. First of all, this is Heights Platform's home base, where it was created and where our founder lives.

Many Heights team members also live in the US, making it easier to travel to the destination.

Austin is also a fun, cosmopolitan city that can satisfy the needs of all kinds of travelers: there are plenty of attractions, shops, food stores, restaurants, nature sites and more.

The weather is also an important consideration when choosing your ideal destination, and the dry, warm climate of Texas was the perfect choice for exploring the city with comfort.

Here are some other factors that should influence your location decision:

• How safe is the area?
• Are there enough attractions?
• Is the location affordable? (in most company retreats, travel and accommodation are paid for by the company, so make sure that these expenses fit into the budget)
• Is the location affordable for everyone? (even if the company is paying for the travel expenses and the accommodation, there may be other individual expenses such as food, rideshare and local transportation, and everyday expenses that employees have to bear)
• Is it easy to communicate with the locals (do they speak the same language, or speak English)?
• Is it easy to reach nearby attractions?
• Is the weather likely to be comfortable when you plan to visit?
• Will your team members need a visa to access the location, or are they allowed to travel there?

Budgeting for the Retreat and Communicating About What is Being Paid for

Heights paid for the team's flights, accommodation, some rideshare/local transportation, team events, and all of the meals the team had together. Outside of full team gatherings, when team members were exploring together individually or in small groups, they each paid for their own shopping, food, and transportation (Heights also gives team members unlimited paid time off). 

We feel that this allowed everyone to enjoy the trip as they pleased without worrying too much about expenses. Since our team is spread across multiple continents, we knew flight costs would vary, but the more expensive flights were offset by the team members who lived closer to or at the destination. 

Choosing the Accommodation

Once you have decided on the perfect location for your company retreat, it is time to narrow down the last details and book the accommodation for your team members.

For our Heights Platform team trip, since some team members were already living in Austin, we only had to worry about accommodating the team members traveling to the city. For them, we used Airbnb and chose listings conveniently located to get around Austin and go sightseeing.

If you are planning your own company retreat, the accommodation will depend largely on the size of your team. When you don't need to accommodate too many people, or if you plan to rent a large villa for everyone, an Airbnb can be a great choice to keep everyone together and incentivize them to build a closer connection.

However, if you are planning a trip for 100 or more employees, booking rooms in a hotel can be easier and more convenient for you and your team members. This way, everyone will still be in one location together, while keeping their own space and privacy.

Planning the Activities

Now that you have booked your accommodation, all there is left to do is to plan the day-to-day activities you and your team members are going to do.

You don't have to plan this in the last detail, however, having a couple of ideas set before the retreat can help you make sure everything runs smoothly.

In the case of Heights Platform's team trip, most things were planned in advance, purposely leaving the first two days free for team members to adjust to the new time zone and explore the city on their own.

The key here is to find a balance between team-related activities and leaving space for team members to enjoy the vacation on their own terms.

Should team members work during a company retreat?

That's up to you to decide. Ideally, you should plan your team trip during a time when you know that the workload is not at its highest, so everyone can have a worry-free vacation. This gives everyone a chance to step away from work, recharge, and get inspired with new ideas to implement upon their return. We chose to treat the trip as a vacation for everyone, and feel it was the right choice for us.

There are a few ways you can handle this as a business owner:

• Don't ask your employees to work during the team trip
• Ask them to complete the most pressuring tasks before leaving
• Find replacements in advance for the week of the trip
• Ask them to work "part-time" while on the team trip

Heights Platform's Team Retreat in Austin, Texas

Let's get into the details of our latest team trip to Austin, Texas. What did the Heights Platform team do?

Day 1

The first day of our company retreat was designed to be a "relax" day, for the team members to recover from their flights and start exploring the city.

Being first-time tourists in Austin, we immediately headed out to visit the Texas State Capitol, a historic building that houses the offices and chambers of the Texas Legislature.

Entrance to the Texas Capitol is free, so our team members enjoyed strolling through the vast rooms and learning about Austin's history and politics.

The Capitol visit was shortly followed by a much-needed lunch stop at a trendy Austin restaurant, where we tasted plates enjoying the Tex-Mex cuisine.

From the restaurant, it was just a short walk to Downtown Austin and its Colorado river, where locals are spotted relaxing on the water.

Day 2

The second day was dedicated to exploring a shopping area, called The Domain.

The Domain is a recently built outdoor shopping center with plenty of retail stores, restaurants, bars and offices.

After a day full of shopping, we decided to take a breath of fresh air and head to the nearby lake, called Lake Travis.

The lake is located just 20-30 minutes West of Austin, and it is the perfect place to admire the sunset with a nice cocktail.

Day 3

While some team members had already been spending time with each other exploring the first two days, on this day, the Heights Team all met up together for the first time of the retreat.

This gave us the chance to record some video content where team members were asked some questions about working at Heights.

After we were done recording, we all headed out for lunch at a typical American diner for burgers.

Day 4

On Saturday, we had a team lunch at an excellent sushi restaurant, followed by walking around the neighborhood and exploring a park.

Here we stopped for some pictures, a coffee and cinnamon buns, before continuing to walk around and visit a bookstore and a local art gallery showcasing upcoming Austin artists.

Day 5

On Sunday, the Heights team met at nightfall to visit a light festival in Austin called Pumpkin Nights.

The attraction consists of a path through a field filled with countless light displays following different themes, all related to Halloween and the spooky season.

Day 6

On the last full day of the company retreat, the Heights team decided to visit South Congress Avenue, a street in the south of Austin filled with vintage shops, alternative stores, bars and restaurants. The area is also filled with the famous, instagrammable murals of Austin.

After enjoying delicious tacos for lunch, we had a walk up and down the street for some last-minute shopping.

Day 7

The very last day of the Heights team trip was a quick one since everyone started heading back to their original locations.

The Heights team gathered for an early brunch at a typical American breakfast place for a last meal together, before everyone started going their separate ways.

Planning an in-person meetup for remote workers is definitely a great way to improve the team morale, create new connections and get to know your coworkers and team on a deeper level. Overall, we all had an incredible experience, and we're already looking forward to the next team retreat!

If you are planning your own team retreat, hopefully, our experience described in this post was helpful, and you can go ahead and start organizing an awesome company retreat!

Interested in joining the team and working at Heights Platform? Keep an eye on our careers page for openings: