What we learned from hosting our first-ever virtual workation

What we learned from hosting our first-ever virtual workation

Even though we’re a remote-first team, we make it our priority to see each other twice a year during workation. This is the time where we physically come together to connect, meet new colleagues and grow closer as a team.

This year, we would have all bonded in sunny Miami. Though it would have been easy to postpone our trip and wait for the next date to meet, we wanted to find a way to still connect—just differently.

Which is how we came up with: The first-ever virtual workation (we’re pretty sure it hasn’t been done before, but you let us know in the comments if it has).

During the 5-day online get-together, we organized workshops, team building activities, an online fair, newcomer presentations, game nights and even a Zoom welcome party (with 78 people!).

Was it possible to grow stronger as a team with a virtual company retreat? Definitely yes!

Even at a distance, the entire team managed to be super welcoming and nice. I wouldn’t trade it for anything else. These are challenging times, but still, it was the best week ever and I learned SO much. Who thought Zoom meetings could get so fun?

In fact, for our first attempt, we’re pretty impressed with how well it was received. Our team rated the experience with a 4.7 out of 5 stars.

By hosting this virtual team experience, we’ve learned that connecting as a remote team doesn’t require relocating your entire team to a great location (although those Miami beaches would have certainly been nice). All you need is creativity, proactive team members that’ll help you set up, the right online technology and your team’s enthusiasm to make the virtual event a success.

We hope these 7 best practices from organizing our very first staycation will help you create a great virtual workation of your own.

1. Invite everyone you like

The good thing about online events is that you don’t need to deal with logistics. You can invite as many people as you like!

We normally only invite team members that have been with us for more than 3 months, but this time everyone could join in on the fun (even developer Mindaugus, who started on our kick-off day).

The same goes for speakers. I was supposed to fly to Texas for SXSW (sadly, it got canceled) and see Rohit Bhargava talk about how to discover non-obvious trends. I was a little disappointed that I missed his talk, but realized that with our online workation, I could just bring Rohit to us.

Surprise! Rohit was so nice to allow us to share his presentation. Click to watch it.

Another great experience that I’ve been wanting to do with our team was the Museum Hack storytelling workshop. Every message that’s told as a story has more impact, which is why our entire team could benefit from learning how to tell better stories.

I’ve been a fan of this initiative since learning about their Metropolitan guided tours. Though they previously only offered this in actual museums, they now turned the workshop into an interactive experience.

During the 3 hours, our team worked together in groups of 4-5 people to create their own narrative from scratch. The coaches gave us storytelling hacks, examples and sent us off to Zoom breakout rooms to unleash our own creativity. So much fun!


Limitations inspire creativity. An online event takes some preparation but it gives you a lot more options to work with. What workshops or speakers would be inspiring for your team?

2. Do “weird and uncomfortable” things together

During the 10 workations I’ve planned, the most memorable moments often happened when we did activities that at first felt “weird and uncomfortable”. Team-building doesn’t happen when things are all about fun and socializing. They happen when things are new and out of people’s comfort zone.

This is why we do unconventional things in each workation, like collectively singing, going on a 25km hike and for this staycation, doing a guided group meditation.

I knew that meditating would be a new, challenging experience for the majority of our team. We already booked this experience for Miami and luckily the same studio agreed to create a presentation and lead the guided meditation online.

As expected, the reactions were mixed. Some loved the pranayama breathing, others felt skeptical about the meditation benefits. A lot of us had trouble “focusing on the now”, as their mind wandered to all sorts of places. After our session, it sparked a whole new discussion about what getting to a relaxed state meant for different people (for our Technical Support star Justas, it’s painting miniatures).


New and challenging experiences connect your team more than fun activities. By putting people in a slightly uncomfortable situation, a team-building exercise becomes a team-growing activity.

3. Make new members the star of their story

As your company grows bigger, it can take some time before you know everyone personally. Especially when you don’t work on the same projects.

We love to keep our team tight-knit, which is why we ask all new team members to create a Pecha Kucha presentation about themselves and present it during their first workation.

For exactly 6:40 minutes, each new employee talks about whatever they like to share—from childhood pictures to hobbies and why they joined MailerLite.

This time we had 33 new members and 33 Pecha Kuchas. Everyone was amazed by how many epic life stories we have within our team!

Our developer, Vincent, is not only a designer but can also pilot a plane, has traveled around with a pimped up camper and loves food photography. From our Support champs, Emma is obsessed with trains, Vanessa is born on Valentine’s Day and Vaida designs her own clothes.

We also discovered that half of our team turned out to be master chefs by night, which led to a new Slack channel #foodies after the presentations were over.

We also heard epic travel stories. The places we collectively traveled are unreal—our team is a real-life Lonely Planet. And finally, having a cat (or three) seems to be a MailerLite thing.

We normally do these presentations in real life, but a surprising discovery was that having them on Zoom actually increased engagement.

While people were presenting, lots of team members were commenting and having entire conversations in the chat. Many of us found out that they had something in common with other colleagues, which shows how connected we are.


Put new team members in the spotlight and let them be the star in their own story. You’ll be surprised by everyone’s hidden talents. Presentations will help your team bond much faster and make new people feel straight at home.

4. Mix up different teams and engage

Last year, we organized our first “MailerFair”—a trade show format where every team presents what they’ve been working on for the past 6 months.

Though some groups work together daily, others had to come together specifically for this fair. For example, Support teamed up with our Partnership Manager, Jess, to see how we can better connect our expert community with our customers.

The interesting thing about this fair is not only that mixed groups have to work together, but also that people can see what everyone’s working on. My question as a COO can be much different than one from a Developer. These different viewpoints help us reveal blind spots and improve projects.

Normally we have an in-person fair with booths, but our online version worked just as well.

How did we organize the fair?

  1. We divided our team into 19 groups according to the projects
  2. Each group had a separate Zoom room and 1 hour to present their projects
  3. 4-5 projects were presented at the same time
  4. People would join the different rooms to come listen, ask questions and comment
  5. Each group did their presentation twice, so there was time for people to alternate between boots
  6. All presentations were recorded

The online presentations were a blast to attend. Many had sent an interactive survey email beforehand and prepared landing pages with our builder (we’re an email marketing tool after all).

HR and support created a “How well do you know your team members” quiz to go with their presentation. In team Editor, all hosts had matching galactic backgrounds. The Data Insight group organized an interactive presentation with a live quiz, using Mentimeter. Fun and insightful!


Think of opportunities to connect different teams and let people present their work to the entire company so everyone can learn about each other’s project.

5. Socialize in randomized groups

Jeff Bezos’ has a two-pizza rule for meetings: “No matter how large your company gets, individual teams shouldn’t be larger than what two pizzas can feed”. We use his rule to plan our workations.

For presentations where 1 person is speaking, it’s no problem to gather with your entire team in a Zoom room. But what about, let’s say, our welcome party? Trying to have a conversation with 78 people is impossible. That’s why we used breakout rooms.

How we organized our virtual welcome party

  1. Our welcome party started with our entire team in 1 main room
  2. Once everyone joined, people were sent off to random breakout room in groups of 6-7 people
  3. They talked for 15 minutes before coming back to the main room
  4. This was repeated until everyone got to see as many colleagues as possible (we went on for about 3 hours because it was so much fun)

We used the same small-group approach for our evening activities. Our team played online games (poker, Jackbox games and Counter-Strike) and Trivia in groups.


People connect better in smaller groups, especially when paired with random people. Though it’s a bit more challenging to organize, virtual workations can be done in groups when you have the right tools.

6. Have fun with DIY activities

From experience, I know that the best activities are those where everyone feels involved. That’s why for this virtual workation, we had the idea to host a movie night. Each team member was asked to create a 1-minute video about their quarantine time at home.

The result was better than anyone expected! People made really funny, creative videos that made everyone giggle from behind their screens. It was great to meet people’s families, friends, kids and pets. You could tell people really made an effort.

It was the start of a new tradition: MailerLite movie night.

Tip: Your team members don’t need to be video pros. For example, Mac users can use the pre-installed app iMovie to easily put together a video.


People appreciate things more when they create it themselves or contribute to the end result, it’s called the IKEA effect.

7. Keep your traditions alive, even online

In true MailerLite tradition, we ask all team members to dress up and put on a wig for our last-day goodbye party. It gets people out of their shell and into their character for the night.

Due to the current situation, some people didn’t have a chance to buy a wig and became even more creative. Instead of wigs, we had team members with a bird nest and a pot on top of their head.


Be yourself and have fun with it. If you have a company tradition, you don’t need to break the pattern, you just need to find a way to take it online.

Final thoughts

We had to postpone our workation and quickly come up with a virtual staycation program instead, but that didn’t keep us from connecting in the same way we would have done in Miami.

We managed to duplicate almost all activities apart from our planned airboat tour to see alligators. Though, if you can rent goats for your Zoom meetings, we could have probably also arranged a virtual alligator meet and greet, if we really wanted to.

While seeing each other in real life is always nicer, it’s definitely possible to virtually connect with your entire team during an online retreat. These 5 days still helped us to connect as a team, get to know new colleagues, reflect on what we’ve achieved and adapt our future vision according to these new learnings.

While this is the time to be physically distant, it's more than ever an opportunity to stay socially connected.