Lessons We Learned From Organizing Our 3rd Annual Company Retreat

May 13, 2019
vgs fiesta 1

It was just another Monday morning. Our engineering teams were getting ready for their standup meetings, the sales team was going through the customer priority list, and HR was checking the schedule of performance reviews and promotions for the week ahead. The sun was shining brightly (what a difference after the record rains in SF in February!), well the Spanish sun kinda always shines brighter.

It was just another Monday morning. The only thing that was different. We were all in the same room.

Nothing beats face to face

Very Good Security has a distributed team. That means we’ve got 67 people from 4 offices in 5 locations, all working together seamlessly from various points on the globe. Thanks to tools like Slack and Google Hangouts, distance has never had a huge impact on our daily communication. In fact, we thrive collaborating across time zones - and we’ve managed to develop a rockin’ culture based on working remotely, all together.

That said, we are also very much aware of the fact that there is simply no stand-in for what teams can achieve with some in-person communication every once in a while.
That’s why we make sure to get together. We just wrapped up our third annual company retreat — and this year it went down in a very special #vgsfiesta atmosphere. (You can find more unique pictures at @verygoodsecurity Instagram account).
vgs team


To “recharge the intangibles that technology can’t capture,” we went to Barcelona. There, under the Mediterranean sun, we spent the whole week getting to know the names of all 67 #VeryGood employees, aligning on the strategy, sharing our achievements, gaining insights from different teams, crushing hacking projects, going for morning runs, celebrating birthdays, eating breakfast/lunch/dinner, and exploring the city together! During our retreat, each team focused on working out issues that are difficult to solve unless everyone is together in one room.

One of the highlights? Our Engineering team organized a real hackathon!

Here’s how it worked:

  1. Before the retreat, team members suggested projects that: were already largely developed, could be done in 1 week’s time, and that any VGS team member could complete.
  2. Projects were then prioritized.
  3. From the resulting list, each person in the team votes for their preferred project. Hackathon teams are assigned based on this.
  4. During the retreat, each hackathon group works on their project over the course of 4 working days.
  5. At the end of the week, each group presents a demo of the hackathon project they whipped up.

vgs hackathon

This is how, in a very short time, we achieved great results. We realized how scalable and fun the hackathon format was, so we expanded it. Now, our sales, marketing, biz dev, and HR groups are planning their own. It’s an engaging and effective way to dive into experiential solutions for problems that they don’t normally get the chance to look into.

Cultivating camaraderie was another goal of our team gathering in Spain. Our Administrative team really knocked this objective out of the park, having planned a successful team-building dinner. Six teams were tasked with cooking six different types of paella. Nothing beats cooking delicious food with your teammates - especially with a few extra dashes of the #VeryGood team spirit.

Lessons we learned organizing the retreat

Planning is king

It starts with planning, then goal setting, setting the goal of the retreat, researching the location, prices, flights, planning the retreat agenda, and ends with resolving issues on-the-fly after the event kicks off. Things happen all the time (projectors bust, buses don’t show up, people get lost), and being ready to take care of unexpected hiccups is essential.

Obviously, the bigger your team is, the stronger the planning needs to be. With more than 60 people, we recommend having a dedicated team that’s responsible for planning the retreat at least 3 months in advance (and managing everything during the days of the event).

Clear goals and expectations are vital

Ensure that teams and individuals set goals for the retreat that map seamlessly into your high-level company OKRs (Objectives and Key Results). It’s very important to foster a culture where everyone on the team understands how their actions impact the whole company’s results.

We recommend starting the retreat with aligning everyone on the company vision, strategic goals, and tactical initiatives. This helps unite the team and power upcoming conversations.

Your time together is very valuable.


When choosing the location, the Internet connection is crucial. Also, make sure that the place is easily accessible for all office locations. Of course, you can’t avoid some jet lag after 14-hour flights (for some), but thankfully we have coffee!

You don’t want to cheat and choose one of your regular offices as a retreat location. It’s crucial to get people out of their day-to-day routines, get them out of their comfort zones, and get them to strategize way outside the box.

Being in your home city simply won’t achieve the same results.

Embrace cross-functional communication

Even within a small company, it is easy for people to become siloed in their areas of focus and expertise. For us, it has been surprising to see just how much our team didn't know was happening in, for example, Product or Marketing, and how inspiring we could be for one another in starting new projects and collaborate on them cross-functionally.

VGS Paella Fiesta

Will we have the team retreat next year?

The answer is a resounding YES.

The following week “back in the office,” we sent out a post-trip survey asking for feedback and suggestions for next year’s retreat.

We might change the format the following year, as we ambitiously plan to grow 3x times. We plan it to become 2-3 days conferences-like with all employees and then splitting into separate streams with separate agendas for Engineering, Product, Sales, Marketing, etc.” - notes Marshall, VGS co-founder.

Retreats aren't cheap, but what's even more expensive is having a remote team that doesn't work well together. Ultimately, the cost of the trip is well worth it in our mind, but you have to make that choice based on the constraints of your own business. For us here at VGS, it is a productive and fulfilling expense that pays off all year-round.
After all, we spend a third of our lives with work colleagues.

It is well worth it to nurture a company atmosphere where everyone is reinvigorated and reenergized after an awesome retreat. People are excited about the work and because they've just spent days hanging out and socializing, they're more comfortable with one another. We see people collaborating that have never worked together before. There is real momentum created with retreats that no other company meeting comes close to imitating.

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Christina Monets Christina Monets

Senior Director of Operations at VGS


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