Building Connections at Help Scout’s Rome Retreat

After joining the Help Scout team in the summer of 2024, I quickly learned that the annual company retreat was a much-anticipated event. We are a fully remote company, so we really value time together to share experiences and ideas, (mostly) away from our computers. The whole team looks forward to traveling to a different city every year, possibly across the world from their home bases, and sharing that experience together.

Though I know everyone enjoys seeing colleagues face to face, as a new hire, I was especially excited to meet everyone in person. Building strong bonds can be challenging when left to Zoom and Slack, and, as an extrovert, I was itching to actually get in the same room with folks.

Of course, if you’re remote and getting ready for your first in-person meetup and instead feel anxious, that’s totally normal! Excitement and nervousness are often different sides of the same coin, and I think knowing what you’re getting into ahead of time can be helpful no matter where you land.

In this post, I’m going to give you the rundown of what it was like for me to attend a Help Scout retreat for the first time as well as offer a few helpful tips so that you can feel calm (or perhaps more hyped) going into your next company gathering.

All roads lead to Rome

We learned that the company had chosen Rome for the 2025 retreat during a town hall meeting the prior fall. Leah Knobler, VP of people, definitely had dedication to the bit, announcing the location in full gladiator garb. And the team was pumped!

I was thrilled by the choice, too. Rome is one of my favorite destinations in Europe. I’ve walked the city many times and have been to its famous sites like the Colosseum, the Pantheon, and the Trevi Fountain, as well as enjoyed simple (but delicious) meals in Trastevere, window shopped while catching the scent of jasmine in the air, and taken in some sun with a glass of wine along the Tiber. I was excited that I would be able to share some of those things with my fellow Help Scouts.

Of course, I knew it wouldn’t all be strolling the ancient cobblestones (or, as it turned out in my case, hobbling them — future me decided to roam Rome in stylish boots vs. comfy sneakers), as there would also be work to do. Since this was my first time attending a retreat, I decided to ask around about what the typical schedule looks like. I reached out to Komal Panday, Help Scout’s people team generalist and the person in charge of retreat planning, and he happily filled me in.

Balancing work and play

Since my goal was to get to know everyone better, I was worried about whether there would be enough time to not only huddle up on work issues but also just hang out. I was relieved to hear from Komal that our retreats are designed to strike a healthy balance between both.

“Each year, we get a little bit better at crafting our retreat week agenda. We have to consider things like the state of the business leading up to retreat and what worked well (and what didn’t) the previous year,” said Komal. “But it’s also just as important to think about things like jet lag, travel time, personal and professional commitments across teams, and ensuring that we’re still able to provide good support to our customers as we’re connecting as a company.”

Komal explained that by prioritizing events like keynote speakers and employee training sessions at the start of the week, the tempo is able to naturally shift toward more social events as the week goes on, giving everyone the chance to recharge and connect on a more personal level.

The retreat agenda was published a few weeks before the trip and I was really impressed with the way the team had thoughtfully peppered in opportunities for informal connections. That feeling was only strengthened once I was on the ground in Rome. There were speed “fikas” to help us all get to know people who we may not have had the chance to work with before, time between sessions for casual conversations, and iced cappuccinos* at the bar for those looking for a pick me up.

While some people took the chance to schedule out their time, others decided to go with the flow. Christian Stein joined Help Scout’s engineering team last fall, and when I asked him how he approached connecting with others at the retreat, he shared that he tried something a bit more easygoing: “I deliberately approached the retreat with a relaxed mindset, aiming to enjoy the experience to the fullest without any undue stress. This allowed me to let conversations and connections unfold organically.”

Our social content producer, on the other hand, got thrown into the deep end. Abigail Bloom joined Help Scout only a couple of weeks before we all landed in Rome, and she needed to use the opportunity to grab some footage for the company socials.

"The retreat for me was all about being in go-go mode for capturing content, but honestly, these moments are what I love most about my job, “ said Abigail. “It gave me a reason to meet new people — and if the company’s culture wasn’t so welcoming, I probably would've been too nervous. Everyone made it so fun and easy to jump in!"

Although she claims otherwise, I know it couldn’t have been easy balancing a new job, international travel, and meeting 130 of your coworkers all in one go, but Abigail handled it like a rockstar. Don’t believe me? Check us out (and follow us) on TikTok and Instagram.

*Quick shout out to Moniker, the company that helps plan our retreats. They know how Americans feel about ice!

Strengthening relationships

With the retreat schedule in mind, I planned to focus my energy on spending time with colleagues. Everyone at retreat hopes to get to know each other better — especially those of us who are new to the company — but a recent change in team structure made this even more important for me.

I’m a product marketer and originally joined Help Scout as part of the marketing team. However, after I had been at the company for a few months, we realized that my role could make the largest impact on the product team, so I switched departments just weeks before the retreat. I saw the event as an opportunity to broaden my relationship with my new teammates as well as a rare chance to meet people I hadn’t yet connected with — like many of the engineers and designers.

One of the aforementioned engineers was Matt Wright, an engineering manager who started with the company around the same time that I did. He had similar goals for the trip: “I tried to make the most of the retreat by casually introducing myself and socializing with as many people as I could. Everyone I talked to seemed happy to chat about Italy, Rome, where they are from, or occasionally (dare I say it) something about work. The vibe was really relaxed, and most everyone seemed quite keen to learn about each other.”

Of course, even when things are easygoing, it can still be hard to put yourself out there. Will Hoekenga, Help Scout’s senior copywriter, explained: "I’m a natural introvert, so my only goal was to keep pushing even when I could feel my social battery getting low. Stay an extra hour at the rooftop party. Have one more conversation before calling it a night. Sit at the table where you don’t know anyone well. While I did take a few moments for myself here and there, I’m glad that I took advantage of just about all the opportunities for interaction the retreat had to offer.”

Whether it was discussing work over dinner, enjoying an impromptu aperitivo at a cafe, or being part of the excitement at the Vatican on the day Pope Leo XIV was elected, my teammates and I made it a point to form lasting connections. As someone who thrives on social interaction and in-person collaboration, these moments lifted both my appreciation for the wonderful team I’m on and my confidence in being an integral member of that team.

Pushing comfort zones

Despite being an extrovert, what made the retreat even more impactful were the moments that pushed me out of my comfort zone. One of those moments was participating in Pitch Party, a tradition where Help Scout team members come up with new ideas for features or programs and pitch them to the entire company at retreat.

I was nervous about the idea of taking part but also excited to share my idea for an “ambassador program,” which would not only improve customer experience but also support our business goals. On one hand, being on stage and sharing an idea that I felt strongly about was empowering — it’s not every day that you get the chance to pitch an idea that could have a real impact. However, putting myself out there, especially in front of so many new faces, also felt a little risky.

Thankfully, there were other retreat first-timers pitching as well. My colleague Ryan Brown is a product manager, and he jumped in headfirst by proposing an innovative and helpful extension of our current AI features. Grant O’Dell from our design team pitched an incredible internal branding tool in the form of a sweet and helpful sidekick character that everyone in the room fell for immediately. Pitching our ideas was a challenge, but pushing through that fear and receiving support and feedback made it a memorable experience.

Of course, there were also less formal (and dare I say, more fun) ways new teammates stretched their limits. Scott Rocher joined Help Scout in 2024 as VP of product. At the retreat, he embraced karaoke: “It would have been easier to stand in the back, have a drink and enjoy the music, but I decided to just say 'yes' to singing. I had support from a few others up there, and it was very fun."

Dillon McDermott, Help Scout’s director of sales, also took part: “I’m not a huge karaoke singer, but I have to admit...I had a great time performing an N*SYNC duo with my man Rylan!”

Though there were lots of moments available for branching out at the retreat, doing so wasn’t a requirement. Matt admitted, “I have a pretty deep well for socializing and was very much looking forward to this experience. But I also appreciated that there was no pressure from anyone to be immersed in every minute of every event. There was space to recharge, which was important for me.”

These experiences — whether they were pushing personal boundaries or finding space for self-care — contributed to the growth of each individual and the team as a whole.

The impact of retreats

Now that the retreat is over, I feel more connected to Help Scout than ever. The time spent with colleagues — whether collaborating on ideas or just having casual conversations — has left me feeling energized and even more confident in my new role.

I’m not the only first-timer leaving the retreat feeling positive. Jesse Kim, a technical program manager, shared how the experience has impacted his perspective: “Being able to celebrate and spend time together in person really helped reinforce the human side of my working relationships with everyone.”

For Dillon, the retreat strengthened the bond within the sales team: “We spent a lot of time together, and I definitely feel more connected to the team than I did before the retreat.” And I believe him — did you happen to catch him and his teammate on CNN?

Christian also felt good about the company’s time together: “I feel a significant momentum and renewed energy impacting my work with the team. The experience provided me with a much clearer view of both the big picture and vision, as well as the more concrete, immediate tasks ahead.”

The retreat served as a valuable opportunity to connect, reflect, and build momentum for the year ahead, and as we get back to our day-to-day work, the relationships and insights from the trip will continue to influence how we collaborate and approach our goals. 

Lean in and have fun

I’m looking forward to carrying this energy into the next phase of my work at Help Scout, and I hope the tips in this post will help you have just as good of an experience at your first company retreat as I did. 

Are you a remote worker who has company retreat tips to share? If so, send them my way, and we’ll share them in a future post!