Help Scout is help desk software for teams who want the personal touch of email support at an enterprise scale. It’s invisible to customers, so every reply you send looks like a regular email, but on the back-end you’re equipped with the right tools for effortless collaboration.

Many of the earliest hires were together in Boston, but we quickly started growing our team outside of the home base. So, kinda-sorta.

To our business model, not much, but to our business, it matters a whole lot.

People who are happy doing what they love in an environment of their choosing. Diversity and the ability to acquire talent from all over the world.

It stems from the founder’s vision of building a company where people are autonomous and take ownership of their work. The acquisition of talent should not be obstructed by proximity. By being remote, we can build a team without borders, and in turn, improve the quality and diversity of our team.

Good communication, especially writing, is key! Most of our communication happens over chat so we look critically at their ability to explain complicated things clearly in writing.  Also, if they have not worked remotely before, I pay careful attention to the questions they have about remote work.  If they don’t have a lot of questions, it’s a red flag.  

The hiring team (3-4 people) interview candidates 1:1 using Appear.in. Occasionally we invite people to our Boston office but mostly it’s video.   

Almost every role we’ve hired for can be remote so we only have one approach for everyone.  If the candidate happens to be near someone on the hiring team, we can do an in-person interview but other than that, it’s the same.

Valuable face-to-face time is a great way to kick-start a successful transition into a remote company so we try to fly folks to Boston (where 25% of our team is co-located) for their first week.  Sometimes it doesn’t work so we schedule a series of video chats in the first 1-2 weeks.  

We don’t place strict rules, but there’s a common understanding that everyone is usually on from the hours of 9 am to at least 6 pm. Slack messages are usually responded to instantly, and emails at least by the end of the day. Every department is different but for the most part meetings are kept at a minimum and contain specific agendas.

Every department is different, but for the most part, yes. The marketing team has what we call a ‘marketing summit.’ Every quarter, we get together in Boston for two or three days and review the last few months, learn from our mistakes and wins, and plan for the future.

Everyone is responsible for punching above their weight. While the expected is 40 hours a week, everyone is well aware of the work and projects that need to get done.

An empathetic understanding of one another’s roles, expertise, and workflow. Over-communication in Slack or on video chat. Honesty, vulnerability, coaching, and feedback.

There’s arguably more overhead placed on the shoulders of leaders in a remote company. The hardest thing is to acknowledge the overhead and be really organized about it. Being transparent and keeping everyone connected is something leaders in your company have to be constantly on top of. Of course, the wonderful tradeoff is a very productive workforce if you get this stuff right.

We have done three company retreats so far, and plan on doing at least two a year. Every time we do them, Nick, our CEO, communicates our mission and values, our progress, and areas where we can do better work. You get a strong feeling in the room that everyone is on the same page. People are up to speed in what every department is doing, what their goals/projects are for the next few months, and what success looks like when it all comes together.

Each team—engineering, support, marketing—shares written updates with one another on Slack. Each team shares what they’re working on, what projects shipped, data to show growth or areas we need to improve, and more.

We also do Friday Fikas—one-on-ones with a random team member where you get on a video call, drink some tea or coffee, and get to know one another.
Goals for the company are clearly defined at the meetings during our retreats, in memos, product updates on Slack, or through the team manager.

Every new hire is given the appropriate tools to do their job well: a new MacBook and external monitor, as well as a stipend to get any necessary programs or tools they need. We also send remote workers the same desk and chair that we use at the office.

We provide unlimited time off, and we highly encourage at least 4 weeks off out of the year. If someone hasn’t taken off in a long time, we ask them to. We trust that every employee will be smart with this, and so far, there has been no issues.

Organically. It was a part of the vision from the inception. Yes, there would be a headquarters, but there was a clear understanding that most of the team would be remote (with the option of coming to Boston as well).

It must in order to do great work. Everyone in Help Scout loves what they do and we all share common values like excellence, craftsmanship, mastery, helpfulness, and more.

When you hire people who embody similar values and work ethic, it’s effortless. When the founders communicate their values and company mission honestly, it resonates with the group at large. Human beings want to do meaningful work and they want to feel like they belong. This doesn’t necessarily mean you have to be shoulder-to-shoulder.

The one thing I’ve personally noticed is how connected everyone feels after a retreat. Stories are shared, everyone is getting to know one another, and everyone is up to speed with the company’s goals. This improves our video chats, communication over Slack, and overall collaboration.

We love the work but we also know when to have fun and connect. Alongside the two retreats a year, we have our Friday Fikas, and randomly we’ll do something where everyone can go to the movies on Friday or maybe a dinner is on the company. We encourage—and are interested—in what people do outside of work, whether social work, coaching, outdoor sports, or building a blog.

Don’t obsess over a beautiful kitchen with an espresso machine or a Zen garden in your office. What is your office for? Clearly define those principles and find your space so you can do meaningful work. It’s about functionality, not appearances. It’s about having a good-enough table to share a meal with your team, not a table where you play foosball.

Hire people who embody your values and are passionate about the mission of the company. While culture-fit is a profoundly motivating hiring decision, remember that hiring “people like you” extends far beyond physical appearances and interests and backgrounds. Hire people who thrive on autonomy, take ownership of their work, and over-communicate with their team. Hire overachievers.

Welcome new hires wholeheartedly. Onboard them with grace and warmth. Communicate your values, the language you use, what you stand for, and how this new hire is going to play an important role in the company—the projects they’ll own, the work that they’ll do. Introduce them to everyone on the team. Provide the necessary tools for them to do a great job. You may have to do some hand-holding in the beginning, and that’s fine—you want this person to feel like they belong, like they’re at a place where, finally, they can do fulfilling work. Go out to dinner and share stories. And then get to work.

I prefer to think of them as trade offs rather than challenges. Office cultures have plenty of challenges as well and it’s important to remain mindful of that. No way of working together is free of challenges.

No matter what kind of culture you have, the biggest challenges are always around people and process. Early on it was difficult to identify the right culture fit for our company, so we made several mistakes. Most notably, we learned that you have to hire people that are already quite skilled and experienced at their craft. Remote work is typically more autonomous, so in order to be productive you have to have done this stuff before.

In Slack, in our video meetings, and in the notes/comments in Trello. We rarely email each other unless it’s a memo for the entire team that contains ideas or thoughts to consider for an upcoming project or event. Otherwise, it’s mostly video chats or Slack. We write to each other like we’re sitting next to each other. We jump on Appear.in for quick 1 on 1s if we need to clarify something or get feedback on something immediate.

We appreciate and understand the necessity of open and fluid communication. We always wonder, “How can we better communicate? What’s working and what isn’t?” We’re also being conscious of diversity within organizations, ensuring that our hiring process is unbiased and welcoming, and our onboarding process makes everyone feel like they belong. We’re growing fast and learning a lot along the way.

Speaking for myself, my work and life are seamlessly integrated. Writing is as much a part of my life as it is my work. However, I do have hobbies and activities that I do regularly. I exercise every day, go snowboarding in the winter, and around 8 pm I hang out with my friends. But for the most part, reading and writing is something I do the moment I wake up and sometimes it’s what puts me to sleep.

• Permission Marketing by Seth Godin
• The 99u Series: Make Your Mark: The Creative’s Guide to Building a Business with Impact
• A Beautiful Constraint by Adam Morgan and Mark Barden

“The most important knowledge is that which guides the way you lead your life.” — Seneca

For me the worst is the coffee shop or out in the open in a public space. I just don’t get how people do it. I need to have tunnel vision when I write and I plug in my headphones and turn up my Noisli app (usually the sounds of rain and a crackling fireplace). The best? My room or a library.