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Last week we had a nice chat with Kaylie, Director of People at Checkly. A fully remote SaaS company that…” that spent a week with us in April.

Based in Berlin and founded in 2018, Checkly helps developers make their websites and web apps more reliable by monitoring them, and then notifies them of issues with those websites and apps before customers find them. Checkly now has 35 employees in 13 countries.

The team focuses on delivering the best product and service to their customers by working asynchronously from all over the world. However, Kaylie and the rest of the team are very aware of the importance of getting together from time to time.

That is why they proudly present (in their very cool hiring playbook) their 2 team retreats a year as one of their perks for joining the company.

"People really look forward to it all year" adds Kaylie.

Checkly's logo
How cute is this logo?


With her colleague Morgan, she is in charge of organizing these essential moments of connection. The objective is always to both connect & align.

Align around a vision and connect with each other.

When we ask Kaylie how they manage to strike a good balance between the two she talks about the importance of creating time with no workshops or activities so that team members can have serendipitous meetings and conversations that end up in amazing ideas.

"We pay a lot of attention to leave space for everyone to be heard and allow for time to work and time to be free".

A team eating a meal in a beautiful courtyard in italy


Everywhere they go, Kaylie tries to plan for activities that make sense with where they are. That is why it is always great to work hand in hand with the team on site.

This time around, our Operations and Event managers Leo & Elisa had a long list of exciting things to do!

"That week we did more than we usually do" Kaylie laughs. "Everyone absolutely loved the guided tour of the property with the owner, such a passionate man", and "the cooking class with locals was also a big hit".

For Kaylie, the bonfire overlooking the valley was the highlight.

"We connect all day and do so much, I expected people to be tired and go to bed early but everyone stayed late".

The power of the campfire worked its charm once again. The team fully relaxed around the fire, eating smores and sharing heartfelt conversations.

a team around the campfire in Italy


When we ask the Director of people what she looks for in a venue she mentions something we've never heard before but absolutely loved:

"a horizontal layout that fosters more interactions".

It also has to have something special, something picturesque, or unique.

A proud team posing with their cocreation

The Workation Village seems to have offered just that and we are very much looking forward to having the amazing Checkly team back!

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