Help Scout
Help Scout

Behind the Scenes at Help Scout's Company Retreats

An inside look at Help Scout's legendary company retreats (and retreat t-shirts)

Remote work is the future. At least, that’s what some of the experts say. Don’t think so? Check out studies from here, here, here, and here.

However, while there are more and more tools continually at our disposal to improve the remote work experience, there’s still something special about face-to-face time with coworkers. And if your company is fully remote, you’ll have to work to make sure this time happens.

One of the best ways to do this is through company retreats –– something our friends at Help Scout know a thing or two about.

Last year, Help Scout took two company retreats, and worked with Real Thread to print soft, stylish t-shirts to mark the occasion.

We decided to ask Bronwyn Gruet, Marketing Designer at Help Scout why these retreats are so valuable for her team, what a retreat itinerary looks like, and tips for designing a t-shirt that appropriately marks the occasion.

Q: To start, tell us about Help Scout! What does Help Scout do?

A: Help Scout makes software for teams that need to communicate with their customers. Our goal is to help companies provide better, more human support with tools for shared inbox, live chatting with customers, and setting up a knowledge base.

Q: What’s your role at Help Scout? What are you working on day-to-day?

A: I’m a marketing designer and illustrator for Help Scout, so my day-to-day is pretty varied! I work with the design team on our marketing site, landing pages, and materials for marketing campaigns. I also make illustrations for our brand, and work on fun culture-oriented projects like designing tees and swag for our company retreats.

Q: You designed a couple of t-shirts for Help Scout retreats in the past year. I’m sure designing t-shirts is something a bit outside of your day-to-day — is designing them a fun challenge?

A: It really is! My day-to-day work is heavily digital, so it’s nice to put my print design hat back on once in a while. It’s also just so fun to see something you dreamed up in your head become something you can hold in your hands.

Q: Are there any particular considerations or differences that go into designing for something physical, like a t-shirt, versus something digital, like the majority of your work?

A: Definitely. Designing something that’s going to be worn by a person comes with different constraints. It means solving for different factors — thinking through how artwork will translate on apparel, comparing colors and textures of fabric, and even just going through a Pantone book to pick ink colors that will interact well with each other.

With digital illustration, you can layer and blend to your heart’s content. With something like a screen printed tee, you’re working within a certain number of ink colors and a specific canvas to design something that’s clear and readable, and also super fun and delightful.

Q: Let’s circle back to the retreat thing. Help Scout works 100% remote, correct? How often does the whole company get together?

A: Help Scout is 100% remote, yes! We have small offices in Boston and Boulder that we use to onboard new hires, but our team works all over the world.

Help Scout hosts company retreats twice a year, always in a different place. Our last couple of company retreats were in Cancun, Mexico and Lisbon, Portugal. In the spring we’re all heading to Dublin for the next one.

Q: What does the itinerary look like for a retreat? How much time do you all spend working versus simply hanging out?

A: The People Ops team at Help Scout always does an amazing job of putting together a schedule that includes talks and teamwork sessions, but also allows for more open-ended time for us to get to know each other better.

Everyone in the company participates in Whole Company Support during retreats as well, and that’s a rare chance to work with Help Scout customers while sitting next to your teammates.

Q: I’m sure executing these retreats, from both a budget and time standpoint, is no small feat. Why is it so important to Help Scout to make these happen regularly?

A: As a remote company, we rely on a-synchronous communication, video calls, and a lot of trust and transparency in order to work well together. Being together in person during company retreats really gives us a chance to strengthen the bonds that other teams form via co-location. Everyone at Help Scout is lovely, so it’s also just so great to hang out with each other :)

Q: What has been your favorite part about company retreats as a remote employee?

A: Having in-person time with coworkers on retreats is just so valuable. Our team is a very kind, smart and talented group of folks, and I love that our retreats become this shared experience that we all connect over.

But also, retreats are a time to meet folks who you may not talk with regularly, and the organic conversations that happen during retreats often lead to ideas that make our work even better when we all head back home.

Q: Why do you think it was important to have a t-shirt made to specifically mark the event?

A: Designing a look & feel for our retreats is another way to make the gathering feel special. Since our company retreats are always in a different place in the world, we love to make artwork that speaks to the place we’re meeting in. Retreat tees become a special token of the cities we’ve traveled to together, and a reminder of a cool experience we’ve shared.

Since becoming a B Corp last year, we try to order the exact amount of pieces we need for the team rather than padding the quantity with extras, which just means the piece really needs to be something special!

Q: When thinking about custom t-shirts for Help Scout — what are the qualities that make a good t-shirt?

A: Design aside, our team loves shirts that are super soft! The way the shirt actually feels does matter, we want them to feel like an item of clothing that you’d actually wear in your normal life. We try to design retreat tees to be playful, graphic, and specific to the place we’re going.

Q: Company t-shirts have a stigma of being pretty corny — do you have any tips on how to design one that people will actually want to wear?

A: Designing company swag ought to be more than just sticking a logo onto a printed item. Instead of designing t-shirts that are focused on what Help Scout does as a business, we like to make them more about our company culture.

For inspiration, we’ll pull from favorite emojis that the team uses on Slack, or draw inspiration from the place we’re traveling to for the retreat. We try to make the design about something the team has experienced together, and just make it something that will make folks smile.

Q: What has been your favorite part about working with Real Thread?

A: The team at Real Thread is a pleasure to work with! Y’all do a fantastic job with print production, every time. We really rely on the person-to-person communication on these kinds of projects, and there’s always a person at Real Thread ready to help us compare shirt styles, talk through Pantone color matches, and make the tiniest tweaks to sizing and placement.

The team at Real Thread is super communicative when it comes to coordinating international shipping as well. Everyone we’ve worked with at Real Thread is helpful, responsive, and insightful :)

Up your company swag game

Looking for amazing t-shirts for your brand? Whether it’s for an upcoming event or general company swag, our team here at Real Thread would love to help you get started. Click here to talk to our team!