The Remote X: Nick of Help Scout

The Remote X is a series by the Planetary team to feature the experiences of remote teams across the world (literally!). Every week, we interview people leading or working in remote teams and share their knowledge with others in the hopes that we can all grow and benefit from their experiences.

Nick Francis is a co-founder and the CEO at Help Scout, which provides help desk software and an array of customer support tools to over 7,000+ businesses around the world. We spoke to him about his personal remote working experience, and the challenges he has faced growing such a huge remote team.

Sketch by Vince Joy.

Hey Nick, where are you based right now?
I’m in Boston!

Tell me more about yourself and what your role is in Help Scout!
Sure, I’m the co-founder and CEO of Help Scout. That role has evolved quite a bit over the last six years! My background is sort of design/user experience, but as the team has grown (we now have 60 people in 40 different cities all around the world), I don’t get to focus as much on that stuff. Now, I mostly work on strategy and the culture.

Is your team fully remote, or do you have an office somewhere?
We do have an office in Boston. At any given time, there’s maybe 4 or 5 people working from there, but everyone else works from home or a nearby co-working space.

Do you find it a challenge to keep yourself focused while working remotely?
No, the nature of my role already has a lot of interruptions, but I don’t necessarily think that’s a bad thing. There’s certainly more distractions when I’m in the office, so if I have a project that I wanna just be heads down on all day, there’s a good chance that I’ll work from home. That tends to align a little bit better for me.

How many days a week do you go to the office?
I typically go to the office 3 or 4 days a week, because I have a small apartment and I like having a desk.

Oh. Do you not have a desk at home?
Uh… a very small one. I’m not even using it right now, so… (laughs)

Why did you choose to grow a remote team? Help Scout is a huge company — was there like a turning point, or was it from the beginning?
It was pretty much from the start. Boston’s a pretty competitive landscape in terms of hiring and when we were just starting out, it was really challenging trying to navigate the Boston hiring ecosystem.

My cofounders and I had spent a lot of time working remotely and weren’t nervous about that — a lot of companies that we really admired were remote companies — so it was a pretty simple decision for us to say “Hey, if we wanna have access to the best people, then chances are, all the best people don’t live in a 20 mile radius of Boston.” If we could structure the culture in such a way that people could work remotely, we could get much higher quality talent that’s really excited about what we’re doing at Help Scout.

How often does your team meet face-to-face or do video conference calls?
Video conferencing is a constant — I’ve already had a couple video calls this morning before talking to you, so we’re always doing video calls. Getting together in person is something that we do once or usually twice a year. Our next trip is to Barcelona. It should be fun!

How do you manage your team and keep them organized/productive?
First of all, it’s about hiring people that love the work that they do, so keeping someone productive isn’t really something that we have to worry about too much. Our people love the work that they do, so we just need to set them up for success.

In terms of tools that we use, Slack is a big one where a lot of discussion happens. Between Slack and email, we use a combination of Trello and Basecamp for different projects on different teams. Of course, we also use Help Scout for customer support and collaboration around that that side of the business, so that everybody can stay on the same page without any difficulties.

Other than those, are there any other apps or tools that your remote team just can’t do without?
Google Hangouts,, and Zoom all have a place on our team when we need to have a video chat. We also use a product called Know Your Company that’s pretty great for getting to know each other.

How much of an emphasis do you put on keeping your team members emotionally connected?
A pretty high emphasis. That’s one thing that you have to be intentional about — simulating the water cooler discussion in a remote culture. We use a Slack plugin called Donut that will randomly pair you up with somebody else on the team to hang out about once a month: we call it Fika, which is a swedish phrase for getting together for coffee.

Some of us will do what we call freestyle Fika. I get together with people on the team all the time. It’s just something that has to be scheduled, and we’re well aware of that, so we make it so that people can very easily schedule that time and hang out together.

“That’s one thing that you have to be intentional about — simulating the water cooler discussion in a remote culture.”

By hang out, do you mean like on Google Hangouts?
Yep, usually Google Hangouts. Sometimes it’s in person — I mean, we see people getting together in the same city for drinks or dinner, and they’ll post a photo. So it could be in person, but most of the time it’s remote.

What’s the biggest challenge you’ve faced while managing your remote team, and how did you solve it (if you have)?
This is a challenge that we’re currently facing: making sure that teams can communicate with each other better. A lot of times people are focused on their own work, objectives and the things that they need to get done, and it’s really difficult to get a good sense of what’s happening elsewhere in the business. Being transparent as the company grows is a lot of work — you have to be very intentional about it.

Is there anything that you’re trying out right now?
There’s a bunch of things that we do to facilitate better cross-team communication: a monthly town hall, quarterly all hands, meetings and OKRs as a company, which are the things that we want to accomplish together in a quarter.

What’s the best thing/your favorite thing about your team?
My favorite thing about the team is their overall level of talent and passion for their craft. It’s a real pleasure to work with a bunch of people that are better and smarter than me in pretty much everything — that’s the company I always wanted to build!

Hiring a bunch of people that I feel are much more capable than I am challenges me to be at my best every day. Today, when we hire, the goal is to hire someone better than you so that we continue to raise the bar and that’s really exciting!

“Hiring a bunch of people that I feel are much more capable than I am challenges me to be at my best every day.”

Describe your remote working experience in 5 words or less!
Uhhhh… I have six or seven words…

That’s fine!
I would say, “Doing great work without compromising quality of life”.

Any last advice for anyone out there working remotely, or thinking of doing so?
My advice would be to make sure that everybody has access to the same information. I think that’s the biggest challenge — you don’t want anybody to feel left out, especially if you have an office but also have remote people. There’s a tendency for the remote people to feel left out. You have to be very intentional about it and ensure they feel like they’re included, valued and capable of doing their best work no matter where they are. If you do that, then you’re in good shape!

Shoutout to Nick for an awesome interview and invaluable advice on managing a remote team! You can find him on twitter at @nickfrancis and at

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