Inside WP Umbrella’s Annual Retreat: Transparency, Team Bonding & Big Improvements Ahead

Building a great product is important, building a great team is essential, which is why every year, we step back from the daily grind to align, reflect, and improve what we do at WP Umbrella.

This year, our annual retreat took place in the stunning mountains of Annecy, and La Clusaz, France. Over a few days, we mixed strategy, deep work, and (of course) some fun—because great ideas often happen outside the office.

Here’s what we tackled, what’s coming next for WP Umbrella, and a few unforgettable moments along the way.

What We Worked On

1. Yearly Retrospective

Over the past year, WP Umbrella has made significant progress, delivering major product improvements and expanding our reach within the WordPress ecosystem and it was nice to be able to dive into. this with the team.

One of the biggest highlights was the launch of several new features aimed at improving reliability, monitoring, and team collaboration. We introduced Safe Update, ensuring safer plugin and theme updates, and built an Alerting Center to centralize notifications and make it easier for users to react to issues. We also expanded team collaboration by adding team member management and introduced multiple sending domains, allowing agencies more flexibility with email notifications.

Additionally, we improved monitoring capabilities with domain & SSL monitoring, keeping users informed about upcoming expirations before they become a problem. A public API was launched to allow developers to integrate WP Umbrella into their workflows, and we completely overhauled our backup system, bringing full control in-house and storing backups in France for improved reliability and compliance.

Beyond product features, we acknowledge that last was a year of strategic expansion and operational improvements. We sponsored TheAdminBar and established a promising partnership with Hostnet, opening up new distribution channels for WP Umbrella.

Our participation in WordCamps and events like WCUS, the Cloudways Hackathon, and WPTuts significantly expanded our visibility within the WordPress community.

One of our biggest operational wins was taking full control over our backups, ensuring data security and optimizing storage. Internally, we also celebrated the successful onboarding of Dorotheja, strengthening our team’s capabilities.

One of the most critical business achievements this year was reducing churn to around 3%. Customer retention has been a key focus, and this improvement shows that WP Umbrella is becoming more essential to our users. However, we know that there’s still room for improvement, and lowering churn even further remains one of our priorities for 2024.

✅ What Worked Well?

Reflecting on the year, several things stood out as major successes. Boris’ management of the Imunify issue was a prime example of how a well-handled crisis can turn into a learning opportunity. Our Black Friday campaign was also a standout success, bringing strong results and confirming that seasonal promotions can be an effective growth driver.

On an operational level, we saw asynchronous workflows become a key part of how we work efficiently as a distributed team. This has allowed us to balance deep work with fast communication, ensuring that development, support, and marketing all run smoothly. Lastly, our presence at WCUS (WordCamp US) was another highlight, strengthening our connections within the WordPress community and allowing us to gather valuable insights from agencies and developers.

💪 What We Could Have Done Better

While we had many wins, we also identified areas where we could have done better. One key takeaway was that we need to trust ourselves more. At times, we overanalyzed decisions instead of moving forward confidently. This is something we aim to improve in 2024—making decisions faster and embracing iterative improvements like in our early days.

Another challenge we faced was support and ticketing management. As WP Umbrella grows, ensuring that customer support scales efficiently is crucial. The friction in our current ticketing system led us to implement Gleap, a tool that will streamline support interactions and provide a better experience for our users.

2. Defining Our 2025 OKRs

We use this time together to define individuals and collective goals for the quarters to come. OKRs (Objectives & Key Results) are our way of setting ambitious yet clear goals. We aligned as a team to define what success looks like for WP Umbrella in 2025, with a strong focus on making our product more intuitive and efficient for agencies.

Since we now have a proper customer support team, we’ve also decided to implement some kind of SLA, to make sure our users quickly get the attention they need when they have an issue with our tool.

3. All-on-Support Session

One of the key moments during our retreat was our All-on-Support Sessions, where everyone—regardless of their role—jumped into the frontline of customer support.

As CEO, I believe it’s crucial for everyone to understand and experience customer pain points—because without our users, we wouldn’t have a company. If you think your coding or marketing skills put you above rolling up your sleeves to help users, then WP Umbrella isn’t the place for you.

Some might argue that having developers or executives handle support is a waste of resources given the salary gap, but I see it as an investment. It’s the best way to embed our mission into the team, stay grounded in real user challenges, and ensure that every decision we make is truly impactful.

4. Mapping Product Friction & Defining the Next Updates

During our last day, we had what we call a “war room” on product friction. War room are brainstorming or meetings, where we don’t go out of the room (but to eat and go to the loo) until our task is not fully completed.

The main task of this war room was to identify all the existing pain and friction of our product, leveraging all the expertise of the customer support department.

So we took a hard look at WP Umbrella’s user experience, listing everything that needs to be improved, streamlined, or automated. The biggest takeaways?

1. ✅ We need a real overview dashboard—something that gives a clearer, at-a-glance view of all sites and the actions needed.
2. ✅ Better logs— so users can track changes more efficiently and see what’s going on in real-time on WP Umbrella.
3. ✅ Smoother workflows—reducing unnecessary steps and simplifying key actions.

The Moments That Made It Special

A company retreat isn’t just about work—it’s also about bonding as a team. Here are a few highlights from our time in La Clusaz and Annecy:

🏔️ Skiing Together – There’s something about speeding down the slopes that clears the mind (and, in some cases, humbles you 😅).

🧀 Tartiflette and Fondue Night – Some of our best product decisions were made over melted cheese and a bottle of wine.

🏖️ Customer Support… in the SPA – True story: we responded to user tickets while soaking in a hot tub. Multitasking at its finest.

These moments weren’t just fun—they reinforced the kind of company we want to be. A team that works hard, takes care of its users, and enjoys the process.