Remote work is on the rise, but how do you go about landing your first telecommuting position?

With the increasing availability of flexible work options, it can be challenging for newbies to sift through legitimate offers versus scams and to know how to put their best virtual foot forward. Even though I am an experienced digital nomad myself, I wanted to go straight to the source to get a bird’s-eye view of the latest trends, job types, and desirable skills for the coming generation of remote workers.

FlexJobs is one of the go-to resources for most people who are diving into the world of telecommuting for the first time, and they hold one of the largest databases for available positions. I chatted with Brie Reynolds, a Senior Career Specialist, to get her insights on the best practices for companies and aspiring remote workers to achieve success, even while separated by hundreds of thousands of miles.

Meet Brie Reynolds, Senior Career Specialist at FlexJobs

My name is Brie Reynolds, and I’m the Senior Career Specialist at FlexJobs. I’ve been with FlexJobs since about 2010. I started out as a college career advisor, and then needed something remote that would travel with me — my husband got a job that would move us around a lot. So I started out actually part time remote at FlexJobs just writing and loved it. I started writing for the blog, doing career advice, and just worked my way into lots of different things. So now I do writing and webinars and all sorts of fun stuff just to help job seekers connect with employers who are offering flexible work.

Do you have any tips for people who are trying to become remote or break into the remote job market?

The first thing to know is that it’s a field that’s definitely coming up. There’s lots more remote opportunities now than there were even just a few years ago. And so if you’re looking for remote opportunities, one of the best things you can do is know what keywords to search for. So you’re searching online at any job board, looking for “remote” obviously is a great word. Virtual, telecommuting, telework — those seem to be the biggest ones that we see companies using.

But then there’s also “work from home” and “work at home” — we typically tell people to stay away from those phrases just because more often than not, it’s scammers who are using them. It’s so obvious, like, “Oh, ‘work from home’ — that’s what I want to do. I’ll search for that.” But then scammers know a lot of people search for that term and they use it to get their scam jobs out there and collect personal data about people, or get credit card information, or what have you.

So stay away from “work from home”/“work at home” and focus on that remote and telecommuting option, and you’ll probably be able to find some good listings out there.

Are there certain jobs that are starting to hire remote workers more frequently?

Customer support is a really good example of an area where lots of remote jobs exist. It’s usually one of the top fields that we see for remote work. The other fields that we look at for remote jobs are things like sales, software development, or computer and IT in general is a big area. Administrative, and then also areas like education and nonprofits, accounting and finance, research. So it’s a wide variety.

Marketing is another big one. And then consulting in all areas is starting to go a little bit more remote, too. So, as a remote worker, if you wanted to be your own independent consultant and put your expertise out there as a freelancer, you could do that. Or, some of the more large consulting firms are hiring for remote workers as well because it’s a lot of travel — you’re meeting with clients and, then when you’re not traveling, you can be working from your home. So those are the big areas.

Why do you think an increasing number of companies are providing remote work as an option to a variety of job types?

First, I think it’s that we have some pretty good case studies now. We have companies who are openly talking about remote work, and their teams, and how they actually do it, and the success that they’re having with it. So other companies see that and think, “Oh, here it is actually being done. Maybe I can do this.” So I think that’s one thing — that more companies are just talking about it. I think another thing is that companies are finally realizing the advantages that come from allowing people to work remotely.

So if it’s cost savings — you don’t need as much real estate. You don’t have to maintain as much office space — all the utilities and peripheral stuff that goes around supporting an office space. For smaller companies, it means being able to expand your marketplace. If you’re hiring sales folks or customer service reps in a certain time zone or location of the world, you don’t have to have office space in that area, and you can get up-to-speed a lot more quickly.

And then also, just the productivity levels are so high for remote workers. It’s shown that they typically are as productive or more productive than in-office workers. So getting more out of your team and also having them be happier and healthier and less stressed at the same time is a pretty good deal. So I think companies are finally starting to see the benefits.

What sorts of skills or personality types should companies be considering when hiring a remote worker?

For companies, I would say one of the things you want to look for are obviously the key skills that it takes to work remotely, or even just work flexibly — if it’s flexible scheduling, or whatever. is actually one of our sister sites, and we’ve interviewed a lot of remote hiring managers and company leaders to figure out — what are they looking for? What are the best skills and attributes?

And they tell us, hands down, communications skills are really key to their remote teams, to their remote companies. So looking for people who communicate really well verbally and in writing — that’s a really important thing for hiring managers to look for. Even if it’s not a front-facing position or a communication-intensive position, you still need people who can commute over that distance that you have when you’re working remotely. So that’s a big one.

Then also, time management and task management and being able to focus yourself and all those sorts of things. Even when working from a coffee shop, you tend to feel like you’re buckling down a little bit more because there’s other people around you also working. But in a remote environment, you don’t have that pressure of people around you working, and so it can be easier to get unfocused. Like, “Oh, the doorbell rang, or I just want to throw that load of laundry in.” So from a hiring manager’s perspective, looking at somebody who understands what it takes to keep themselves on track and focused on whatever task they have to do, that’s a really important thing.

Technologically, you want to look for people who have high-speed internet and have the appropriate equipment that you’re looking for so that they’re connected all the time, and that they can actually be available and not constantly be worrying about internet connections and all that sort of stuff. All of our internet gets a little wonky every now and then, but for the most part, you want to have people who have a fairly strong internet connection.

One of the interesting things is that some remote teams provide equipment for their workers, and then other remote teams allow their workers to choose their own equipment. So that’s something you would want to consider beforehand. So do you want to allow people to choose their own equipment and maybe give them some parameters to go by — if it has to be a Windows PC or a Mac — and then otherwise let them choose their own stuff? Or do you want to provide them with the specific laptop with the software they need and all that kind of stuff? So that’s something to think about ahead of time.

What is one piece of advice you would give someone who is just embarking on their first remote position that you wish you’d known before you started?

I would say, understand that it can feel a little bit isolating sometimes, and that’s something to expect and to not freak out about. I like working alone, most of the time. I tend to work in a pretty quiet environment. I’ve been working completely from home since 2010, so over the last seven years or so. And I love it. But for some people, they really crave that in-person interaction. They want to get out there and see people, and just be around people. And you can do that as a remote worker. So that’s one of the things I would say. Set up ahead of time in your head — where you can go to get that people fix? Whether it’s setting up lunch dates with your friends, or just working from a library or a coffee shop or a co-working space.

Think about different ways that you can get your people fix so that you get out of that isolated feeling and you don’t feel like, “Oh, remote work, I shouldn’t be doing this. I don’t like that feeling.” Because it really is great overall. But I feel like people start to get that feeling and they think, “Oh, maybe I don’t — this isn’t something that’s cut out for me.” But it can be, as long as you know where to get your people fix.

Even for somebody like me, who loves working very quietly and alone most of the time, there are times when I’m like, I just need to get out of the house. I’ll go to a coffee shop or the library, even, and it just has that level of human interaction that we all need as people.

I would also say a quiet home office space is a really key one. Even if you live in a tiny apartment, if you can just carve out a little corner someplace that has a dedicated desk and a good, quiet space for you to work from that’s free of distraction — whether you’ve got roommates or kids or dogs or what have you, just make sure you have a space that you can go.

Especially if you’re working in customer support, that’s one of the number one requirements we always see is you have to have an office space somewhere to go so that people don’t hear all the stuff going on in the background.

Do you find that for remote workers there are more challenges with work-life balance?

I think it depends on the job and the person. I know with work-life balance, most remote workers feel that it is a little bit easier because you don’t have to commute in the morning. You’re not worrying about what you’re going to wear all day, every day and maintaining that wardrobe. It’s really easy to get lunches made, and all that sort of stuff because you’re in your house. You have this whole kitchen available.

But then also, sometimes work can really bleed into life easier because your work and your life happen in the same place. So it’s important to set boundaries.

I think one of the things people don’t realize is that they might end up working more when they work remotely, because they forget it’s stopping time. There’s no train to catch. There’s no traffic to avoid. It’s just like, “Oh, you can keep going if you want to.” So watching out for that overwork and trying to maintain work-life balance that way is key for a remote worker.

Do you notice certain age demographics who gravitate toward remote work?

It’s pretty spread out. We’ve done some surveys at FlexJobs, and FlexJobs include all types of flexibility, so a lot of our jobs are remote jobs, but we also offer freelance, and part-time, and flexible schedules. So the surveys that we’ve done encompass people who look for all types of flexibility. But the number one thing people tell us they want is remote work.

The people we’ve surveyed, they say they want remote work, and they’re generally somewhere in that 35 to 55 range for the most part. They’re not necessarily entry-level, super young folks. A lot of it is just those mid-level career professionals who have worked in an office for a while, and they’ve decided they don’t want to do this anymore, and they would rather be from home. So that seems to be the main group, but then we do see a good number of first timers in their careers, or entry-level folks, and people who are towards the end of their careers and either looking for a way to ease into retirement or to have a second act after they retire and do something different with their lives. So it’s a wide variety of people.

Have you noticed any challenges companies have faced while trying to increase the diversity of their workplace?

We have seen some interesting initiatives where folks are both hiring for diversity or are keeping diversity in mind when they’re hiring and then also putting in place things like employee resource groups to support the diverse workers that they are hiring. And actually remote employee resource groups are coming up,too. So not that that has to do with really diversity, but it is one of those ways where you see support overall becoming more important for companies.

Larger companies are really saying, “OK, who are our workers? What do they have going on in their lives? Where are their challenges? Where are their commonalities and differences?” And putting support groups in place — employee resource groups in place to support them when they come in. The nice thing about an employee resource group for diverse populations is they’re typically run by the employees themselves. So they’re people who are in a situation to understand what somebody else is going through based on whatever demographic they’re coming from or reality that they’re in, whether it’s military spouses or by gender or whatever it might be. And so it’s really nice that they’re tapping into employees who are already in that situation and have the ability to share their information and knowledge and support one another.

As far as diversity in hiring goes, we’ve definitely seen — I don’t know if it’s a steep uptick — but it continues to be more of a focus for companies. They’re continuing to keep it front of mind while they’re hiring. And also, we’ve heard from some companies who actually use remote work to tap into populations that they aren’t able to get in the office in a traditional way — people with disabilities, military spouses, folks in really rural communities, or places that have poor economic situations, places that haven’t recovered since the recession, stuff like that.

Companies are using remote work as a way of hiring those folks and keeping them where they are, but getting them back in the workforce and getting them working again.

Ready to nab that remote position?

Having a virtual job frees up your time, increases your personal flexibility, and allows you to better balance the different elements of your life. However, it’s key to set yourself up for success by ensuring you have a private dedicated workspace, time with other humans (or it might be time to adopt a furry companion), and the gear you need to execute your professional responsibilities. Be sure to highlight those communication skills, and come up with concrete examples of your dedication to work, no matter the external pressures or distractions.

Cecilia Haynes
Cecilia Haynes

Cecilia is a content strategist and Help Scout alum. Connect with her on Twitter and LinkedIn.