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Help Scout's Company Retreat in Rome.
How Moniker helped a remote-first team of 115 build trust, deepen culture, and finally let their people team actually enjoy the retreat they planned.
Remote-first since 2011.
Help Scout has been fully remote since before most companies had a work-from-home policy.
For over a decade, their annual retreat has been the one time each year when their globally distributed team actually occupies the same room, eats at the same table, and remembers they’re not just colleagues on a screen - they’re a team.
As Help Scout grew from a scrappy 30-person startup toward 100 people, their people team lead Leah kept ending up in the same position: spending every retreat working, not enjoying it. She needed a partner who could own the whole operation, and genuinely deliver.
After strong recommendations from teams at Zapier and Webflow, she found Moniker. That was six years ago. She hasn’t looked back since.
“When you work with Moniker, you have a team and feel supported at every step. Planning a successful retreat is all about attention to detail and logistics, and Moniker has just consistently nailed that — blowing it out of the box.”
“I love the first day where everyone sees each other for the first time.
That feeling is contagious.”
Five days, packed with purpose.
From Welcome Reception to last-night Karaoke, every moment was intentional — structured enough to drive alignment, loose enough to let real relationships form.
Welcome to Rome
~100 guests scattered in throughout Sunday and Monday. Hotel check-in at 3PM, followed by a Welcome Reception at the Lobby Bar Terrace, 6:30–10PM. The energy in that lobby? Electric.
All Hands, All Energy
Full company meetings, training sessions, manager meet ups, group photos, happy hours, and of course, leisure time!
Breakouts & Trastevere
Brand Moments, panels, team breakouts, and pitch parties. Evenings: dining around through the Trastevere neighbourhood — Meo Patacca, Fieramosca, La Gattabula.
Roam in Rome
Kicked off the day with product a C-Team sessions, then the whole company fanned out for "Roam in Rome" — an afternoon of guided city exploration, followed by Villa Pamphili dinner at Acquaviva.
Karaoke at Chigi & Baschi
Group Dinner and then off to close the trip out with karaoke from at Chigi & Baschi. A Help Scout tradition.
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Final Breakouts & Goodbyes
Team Breakouts in the morning, then scattered departures from midday. The city had done its job. Everyone left a little different than they arrived.
"Before working with Moniker, I never able to fully enjoy these retreats because I was always working them. It was a huge shift to finally be able to have partners who do this."
Every detail handled. Every person present.
When Moniker takes on a retreat, every person actually gets to enjoy it. Here's what that looked like for Help Scout.
On the ground, the Moniker team embedded fully — moving fluidly between Help Scout staff and hotel operations, anticipating needs before they were voiced, and becoming, in Leah's words, “fun celebrities” the whole company was excited to see.
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End-to-End Planning
From the first venue call to the last departing taxi, Moniker owned the entire operation. Every vendor, every hotel block, every meal. Nothing fell through the cracks.
Rome as a Strategy
The destination wasn't chosen for convenience. Rome was chosen because it demands you slow down, share a meal, and actually talk. The city did half the relationship-building work.
Fully Embedded On-Site
The Moniker team didn't manage from a distance. They were in the hotel, at every meal, between the company and the venue — an invisible hand keeping everything running smoothly.
“Before working with Moniker, I was never able to fully enjoy these retreats because I was always working them. It was a huge shift to finally have partners who do this.”
“Before working with Moniker, I was never able to fully enjoy these retreats because I was always working them. It was a huge shift to finally have partners who do this.”
Leah — People Team, Help Scout
This is what it feels like months after.
For Help Scout, this isn't a nice-to-have. It's a productivity spark, a motivational spark, and a cultural investment that compounds over time. The week after a Moniker retreat has a recognizable signature: new inside jokes, shared photos, renewed momentum.
Coming out of Rome, there was a different energy and pulse across Help Scout — palpable in Slack, visible in the work. The kind of thing that's hard to manufacture and easy to lose. A well-run retreat gives you months of it.
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Team members who arrived as coworkers and left as friends
Trust, Deepened
New relationships formed. Existing ones strengthened. The kind of trust that makes remote collaboration feel less like a workaround and more like a feature.
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Days that shaped the culture for the rest of the year
Alignment, Renewed
Everyone left Rome pointed in the same direction — clearer on the mission, more connected to the people working alongside them, and more motivated to do good work.
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Years Help Scout has trusted Moniker to continue to plan their retreats
Momentum, Felt
New inside jokes. Photo-sharing that kept going for weeks. A different energy in the Slack channels. That uplift is real, measurable, and worth every penny.
"It's such a morale boost. There's always that uplift in the week after a retreat — a different energy and pulse. New inside jokes and reference points. Everyone's sharing photos. It really just continues that feeling."
What Help Scout actually said.
“Having a team that truly has your back at every step — one that handles every detail so you can actually show up and enjoy the experience yourself.”Leah — People Team, Help Scout
“Finally being able to enjoy our own retreat. Before Moniker, I was always working through it. Now I get to be present, just like everyone else.”Leah — People Team, Help Scout
"How embedded they become — not just with the planning team, but with the entire company. Everyone knows Erin by name and gets excited to see her. That's not something you expect from a retreat planning partner."Leah — People Team, Help Scout
"Teams that want to stop worrying about the details and actually show up for their people — especially if you're remote-first and you know just how much these in-person moments matter."Leah — People Team, Help Scout
"Teams that want to stop worrying about the details and actually show up for their people — especially if you're remote-first and you know just how much these in-person moments matter."Leah — People Team, Help Scout
Plan a retreat your team will actually remember.
Whether you're bringing together 80 people or 300, Moniker handles every detail — so you can show up and enjoy it too.