Jonathan Sumner Evans
Sumner Evans
Software Engineer at Automattic working on Beeper

Porto, Portugal - Work Retreat

Posted on in Travel, Work Retreats • 2479 words • 12 minute read
Tags: Porto, Portugal, Beeper, Automattic, Work

The past few weeks have been exciting for Beeper. We made Beeper available to everyone without a waitlist, launched a new Android app based on our own internally-built Matrix SDK written in Go, and were acquired by Automattic for $125M. As part of the acquisition, the Beeper team is merging with the that was acquired by Automattic last year. We are going to unify the products under the Beeper brand. All of this is only a few months on the heels of our Beeper Mini launch which brought fully end-to-end encrypted iMessage to Android devices.

Like Beeper, Automattic is a remote-only company and so is the team, so work retreats are the only time that we can connect with our co-workers in-person and build stronger personal relationships with among the team. This retreat felt especially necessary because we are combining two teams together and we wanted to build personal relationships across the previously separate teams.

Our destination for this retreat was Porto, Portugal. We’ve had a retreat in Portugal before, but not in Porto. We also have had retreats in Montreal, Playa del Carmen, Mexico City, Amsterdam, and most recently in Toronto last fall.

The Venue

The meeting area was on the hotel grounds about a hundred yards from the front of the hotel. It consisted of two main rooms: one with circular tables and a stage and one with couches and chairs and an array of snacks and coffee. It was very fancy compared to our previous retreat, which makes sense because a whole event team had been there setting things up for a few days before our meetup. They had nametags and swag ready for us when we arrived and there was a whole AV setup with TVs and livestreaming equipment. They had tables set up for everyone and a small stage in the front. This is definitely a benefit of being at a larger company: we have actual teams that organize larger retreats. In the past, it’s mainly been Eric handling all of the logistics, which is a lot of work and his bandwidth was not primarily dedicated to event planning.

The coworking space setup for us

The hotel itself was very nice as well. The room was large and luxurious and the hotel’s restaurant felt high quality for a hotel. We had breakfast every day at the restaurant (well, we being the general “we”… I skipped breakfast a couple days due to sleeping in too much) and they also provided lunch and a few dinners.

Getting to Know Everyone

In addition to the Beeper and Texts teams, there were quite a few Automatticians in attendance who helped facilitate team-building and integration into Automattic. My goal for the week was to have at least one memorable conversation with everyone from the team and get to know some fun fact about them other than just where they’re from and what they work on. I did have a conversation with everyone, but meeting ten new people is difficult and I feel like I need another retreat in a couple weeks just to get to know everyone better!

We did a couple activities which encouraged everyone to mingle and talk to new people including a variety of ice breakers on Monday, assigned random tables for some of the meals, and flash talks. The ice breakers included an activity that was a set of puzzles that each table had to solve, a speed networking session, and an activity where we had to create something which represented “Messaging at Automattic”. Many of the teams used generative AI for that activity to create images and even music about messaging at Automattic.

I also really like the assigned seating for some meals (I think it would have been annoying if it was assigned for every meal) because it forced us to sit with different people. I did an OK job of sitting with different people on my own, but having the forcing function for some meals was nice. I’ll describe a couple of the most memorable conversations that I had here.

On Monday, I ate breakfast with Kishan (CEO of Texts), Javier (reverse engineering specialist at Texts) and a few people from Beeper. Then, at lunch I sat with Rafa, Matt, and Dylan. Rafa and Dylan came from, and Matt transferred to the team from another team at Automattic (I think Tumblr). We discussed I blabbered about HTMX and about how I believe that more web apps should be rendered server-side and we should generally rely less on client-side rendering. We discussed that this trend towards server-side rendering seems to be happening in other areas of the industry with React Server Components and other server-side rendering optimizations for traditionally client-side rendered frameworks.

On Wednesday, after the walking tour we went to a winery for dinner and I sat with Rida, Skip, and Meaghan, among others. Meaghan is on the Developer Experience team and she shared some insights into how past acquisitions have gone from the Automattic side of things. As I’ll talk about later in the post, Automattic’s culture is different from Beeper’s in many ways, but there are many similarities as well. I think that it will be an adventure to adapt to the new culture we find ourselves in, but I think it’s a journey worth taking. In my discussions with Rida, I learned that he was the one of the main writers behind the scathing Sunbird / ‘Nothing Chats’ is Not Secure blog post that the team produced after Nothing Chat’s release. It was a masterful work of reverse engineering that was widely reported on and effectively killed Nothing Chats as a product. Skip told me that he’d actually considered applying to Beeper since he was friends with a former employee, but decided against it and ended up getting hired at for his Discord reverse engineering work. It’s come full circle now and he’s working on Beeper anyway! The industry is very large, but within a niche, it seems that the degrees of separation between people is very small.

After dinner every night, there was an open tab at the hotel bar. I went to bed on the first three nights since I was still trying to fight the jet lag, but on Thursday I was feeling energized enough to go over to the bar. I had a really nice conversation with Ellie who works on Pocket Casts. I have used Pocket Casts for a long time, and love the product, so it’s cool to now work at the company behind the product. I also spoke extensively with Kevin about what he looks for on resumes for junior engineers. We don’t hire any junior devs at Automattic, but he’s hired junior engineers at previous roles. (I think a big reason for not hiring juniors is because it’s very difficult for juniors to come into a remote-only entirely asynchronous company. I learned that even the daily standup meetings that Beeper has is rather abnormal at Automattic.) Kevin gave me some really good tips to bring back to the students that I interact with at Mines to improve their resumes and help explain which extracurricular activities benefit career growth.

Friday was a travel day when most people were leaving. In the late morning, the people who hadn’t left yet were hanging out in the lobby of the hotel and Kishan brought out his Apple Vision Pro and let all of us give it a whirl. Most of the people left were employees, and it was fun to try out the new technology and interact with some of my new teammates and just nerd out about the cool technology.

I’m definitely more extroverted than I was as a kid, but meeting people for the first time is still difficult. However, when everyone you meet is kind and welcoming, it makes that process so much easier. All of the long-time-Automatticans were very accommodating and helped me understand what working at Automattic will be like. All of the people are very enthusiastic about chat, and I look forward to working more closely with all of them.


As I mentioned before, there are many similarities between Automattic and Beeper. Most obviously, we are remote-only companies, so that part of the transition has gone very smoothly. However, over the years we have had developed a variety of processes and a unique culture at Beeper which has many differences to how Automattic works. I think that the cultures are very compatible, but I think that it’s going to take some time to meld the two together.

On Monday, Ronnie led a discussion about change vs. transitions. The main goal of the discussion (as far as I could tell) was to get us to differentiate between change (things which just happen to us and are outside of our control) and transitions (conscious decisions to evolve processes and mindsets). Change necessitates transitions. For us, the main change is that Beeper was acquired and it’s on us to transition to the new reality. So far, everyone at Automattic has helped make this process as smooth as possible. Even just the fact that we were acquired as an entire team signals to me that Automattic really wants to invest in Beeper not only as a product, but as a team.

On Tuesday, we had a very short AMA session with the Beeper and Texts leadership as well as Sonal who leads the Other Bets division (of which Beeper is a part). I have confidence in the leadership team of both Beeper and Automattic, and I see a lot of willingness from leadership to support both the development of the Beeper product and the integration of the Beeper team into Automattic.

Flash Talks

Part of assimilating into the Automattic culture was giving flash talks: short four-minute talks about a topic. Everyone at the meetup had to give a flash talk, and each day a few people gave a talk. The topics ranged from a talk about Texts’ architecture by Batuhan to a talk about The Yooper (the Upper Peninsula of Michigan) by Josh and from a talk about running shoes by Bradley to a talk about Minas Gerais (a state in Brazil) by Wellington. Many of the talks topics were somewhat predictable considering the demographic: there were a few talks about various video games (Magic and Dota come to mind) and talks about 3D printing, hacking routers, and AI. But many others were quite surprising and really showed the diverse personalities of the team.

A fan favourite was Adam’s “Lettuce or Cabbage” flash talk where he went through a series of pictures of cabbages or lettuces and had the audience shout out what we thought they were. We were pretty horrible at the game. Eric also played a game of “TV Show or Real Life: Silicon Valley Edition” where he described a bunch of startup ideas and we had to guess if they were from the show Silicon Valley, or from real life. It turns out that all of the ideas that he presented were real, despite many of them sounding so outlandish that you would think that only a TV show writer would be able to contrive such a “business”!

For my flash talk, I talked about my history with blogging. Automattic’s flagship product is WordPress, so I thought it would be fitting for me to talk about the various blogs that I’ve had over the years. I started blogging when my mom had us write about our six-week trip to Vietnam in 2010. The original posts are on an old Blogspot blog and you can actually find them on this site as well. I had a WordPress blog for a few years, and I’ve had this blog in various forms since around 2017 with the most recent large change being in 2020. It was fun for me to look back on my blogging history and remember the reasons I do this: I want to document the good times in life so that I always remember that I have so much to be grateful for.

So I Hear We Got Acquired by a Blogging Company

Me giving my flash talk

So I Hear We Got Acquired by a Blogging Company

Walking Tour

On Wednesday, a large group of us went on a walking tour of the city. Our tour guide was a Porto native, and took us to some of the main sights in the city. I’m going to defer my discussion of the things that he talked about to my next post about my extra day in Portugal sightseeing, as I want to keep this post focused on the meetup itself, but I’ll post a few photos of our group right before and right after the tour.

I thought more people would join me and Annie with the sorority squat. PC: Megan Marcel.

The walking tour crowd

I thought more people would join me and Annie with the sorority squat. PC: Megan Marcel.

Josh has a really cool 360° camera. PC: Josh Johnson.

The team at a great overlook with views of a lot of Porto

Josh has a really cool 360° camera. PC: Josh Johnson.

Planning a Glorious Beeper Future

During the week, we had many co-working sessions where the individual teams got together and planned out a variety of initiatives. As Brad described in our How Beeper Android Works blog post, we are building a core Go library for our clients. The Android app is already using it and the desktop a iOS teams began work on integrating it while also combining the Beeper and Texts codebases.

We are also building towards more local bridges like the experimental Signal bridge that we announced in that blog post. As part of this initiative, the team I’m on (the Platform team) kicked off a large refactor of all of our bridges to reduce code duplication and increase standardization of features across the bridges. The Platform team also mapped out plans for increasing the reliability of Beeper’s server infrastructure while reducing costs.

I’m excited about the future we are building towards. Our vision has not changed: we want to build the best chat app in the world. The combined Beeper and Texts teams have all of the best chat network reverse engineers, and we have a team that can give any team in the chat space a run for their money. Everyone on the team is highly competent and motivated towards the goal of de-siloing the chat landscape. But in order to de-silo the chat landscape, we must de-silo ourselves. This retreat was a big step towards that goal.

It’s cliche to say, but I truly believe that our combined Beeper/Texts team is greater than the sum of its parts. The teams have been working on similar products for a long time, but now we are joining forces. Combining the knowledge of the two teams will take time, but I think that we will emerge from this transition as a strong, unified team ready to take on any challenge we face.