How to Land Your First (or Next) Remote Job

I landed my first remote job accidentally: it was in a tiny back office in Gastown, Vancouver and I had worked there for about a year before my bosses suggested that I work from home a couple of days a week. I thought I had landed the work lottery. I'd always craved self-management and flexibility, so all of a sudden, a job I liked kind of became a dream job. I pictured myself living the nomad life: maybe this was the beginning of my wildest dreams come true. And I didn't even know to ask for it before it had become my reality!

It was amazing at first, but looking back, I don't think it went as well as it could have. I've always had a habit of front-loading my work mostly because I like the feeling of being ahead so that I can relax later. So, all of a sudden, with no one to talk to (it was a three person team and we didn't have anything like Slack), I found myself twiddling my thumbs for most of my day. The spaces that were filled with office chatter – sometimes small talk but not always: we'd make strategic plans too – became empty. And soon, disengagement settled in. This was early enough in my career where I didn't know any better. I didn't know how to ask for what I needed, and certainly couldn't recognize the signs before it was too late and I was looking for a door out to seek ‘new challenges’.

My next remote job went much better because I had the support, the systems, and the structure of a remote team in place. Soon after, I started leading a remote team, made up often of people for whom a remote job was, just like mine once was, brand new. I've seen all kinds of challenges, from extroverts who always felt like they were missing out on something to the fragility of systems without a source of truth turning simple tasks into time-wasters and misunderstandings.

As more people and companies adapt to either full-time remote work or the option to work remotely part-time, what was once a novel rarity has become more of the norm. And these challenges? We're just starting to learn from them: that remote work is still a dream for many (and a nightmare for some), but one that we need to be fully awake and present to – a.k.a you can't just autopilot your way to remote work paradise.

In this article, we'll explore ways to assess whether or not a remote job could be right for you (basically: not just perks and benefits but ways to think about: is this the best fit for you, your lifestyle, and your career goals?), as well as tips and resources for getting your first (or next) remote job.

Is remote work right for you?

You're good at self-management

For every person who's self-motivated to make an impact at work, there are people who just… aren't. Which is fine, work can't be a passionate love affair for all, as much as we've been fed this narrative. Work at its simplest is a way to make money, an exchange of value for value. And if that's the way it is, then wouldn't it be nice to get paid to do the minimal amount of work? To show up and do just that and not much more? With remote work, that's possible. Get your work done in the first 3 hours? (That's the average number of productive hours in a workday, according to various studies.) Why not watch cat videos and surf the net the rest of the day? No one will know, right?

Well, not exactly. Start thinking that way and you're entering a very slippery slope. The type of personality that needs external accountability (like the pressure of looking like you're busy) could fall behind in a remote work environment, which could have long-term repercussions on mental health, career growth, motivation – even if it feels good in the moment, even if no one else notices (see: case of man who skipped work for six years and no one noticed).

So think very carefully if the appeal of remote work to you is absolute freedom, if you can't handle the weight of it.

You require or prefer flexibility in hours at work

Typical work hours tend be in the range of 9-5, but if you've been jumping on the chance to work a 6-2 job because you're an early riser and that much more productive in the morning or 11-7 because you're not, remote work could be the perfect way to get the schedule of your dreams. I once took a 4-12 midnight remote job because I didn't have a lot of employable skills but I needed to make money. I wouldn't have taken a 4-12 midnight job that required me to be on-site. But working at home? I'll take it. And it was one of the most pivotal decisions I made in my career, one that I can trace back to from the career I have now.

Just make sure to check that the job doesn't require specific hours, which they can sometimes.

You've got some work experience under your belt

This is not to say that there aren't people who can thrive working remote right out of the gate as their first ever job. There probably are, especially in an environment that sets them up for success. But there are a lot of things that come from being in an in-office environment that just aren't all that common and much more challenging to get as a remote worker, like: mentorship, visibility, and knowledge and skills picked up through observation. (Doubly so if the remote company you're working at isn't established in their remote work processes.)

These things matter less over time as you build your career and network, but they can make a big impact for the long-term trajectory of your career early on.

All that said, it's not impossible to get these things early in your career. You'd have to be much more proactive, and know what you need too (which is really really hard to identify in these early stages; I've been there). It's like the phrase: You don't know what you don't know.

If you really feel a remote job is right for you, it could be a case for finding a job that offers the option to work remotely some of the time, so you get the best of both worlds.

You want to be measured by the work you do

Remote work strips away a lot of the in-office accidental politics that can come from personality-driven biases. (Not that it strips away all of that, or that there aren't other kinds of biases that come into play in remote work.)

It's the best way to bring the concept of ‘show up and do the job’ into focus in your career, and have that be the primary metric for promotions and raises.

You have high emotional intelligence

When you're working remote, a lot of the communication cues we're so used to having when speaking to people face-to-face are gone. We're left with a primarily text-based environment, with some shoulders-and-up facetime sprinkled in between. That means remote work can be hard for someone who can't pick up on these cues in text-based communication or who takes it personally when language feels overtly straightforward because you can't see a smile* or because that's just the way they write.

*Enter the overuse of slightly smiling faces: 🙂 (guilty).

This can be really tough for some people, creating an environment where they can't thrive because things might always feel shaky to them. Remote work is much easier if you're someone with a high degree of emotional intelligence (both for yourself and to build that trust with your team) and resilience (which can be developed).

You're introverted

While both extroverts and introverts can thrive in remote work, you may find that as an introvert, remote work is a big win and sets you up so that you can be yourself and not feel burned out at the end of the day.

With remote work, there's less pressure to respond to people right away (whereas, you can't exactly ignore a tap on the shoulder). 

These things are not always easy to come by in physical offices, especially in the Millennial dream workplace: where there are no doors and no cubicles and you're around people all the time (pretty much the opposite of what introverts want.)

You're ‘open’

There's been a lot of studies on the impact of remote work on mental health, especially over the last year. The results seem to vary, with some claiming that there's a positive effect and others claiming that it leads to even more burnout. So what gives? Well, it might depend on your personality. A study conducted by Oklahoma State University found that ‘openness’ was a key characteristic of people who were the happiest to embrace remote work. At this point, it makes sense: remote work is new and it changes a lot of what we grew up thinking work should be.

I have a feeling that things might shift as remote work becomes even more of a norm in the decades to come, especially as more companies get set up properly and managers become more adept at remote leadership. For now, if you like to try new things, you might find adapting to remote work much less stressful.

What kind of jobs can you get as a remote worker?

Well, almost anything really!

• Development

• Design

• Project management

• Virtual assistance and admin

• Customer service

• Marketing

• Content

Recent adoption means almost any role can be remote now, especially as more support and tooling becomes available and adopted by industries and niches.

Where to find a remote job

• We Work Remotely

• FlexJobs

• JustRemote

• Remote OK

• AngelList

• LinkedIn

• Industry-specific Slack groups and job boards like:

• • 80,000 Hours for jobs that tackle global challenges

  • Business of Fashion for the fashion industry

  • Designer News for designers

  • Superpath for content roles.

• There are a lot of online communities out there, and most will have a channel for job opportunities, including SuperHi (#opportunities). These will often have a much higher ratio of remote jobs, as the communities themselves have a global audience.

• Ask for leads among peers who you know work remotely.

Tip: LinkedIn is much harder to search for remote jobs as there's not really a great way to filter remote jobs. 

Also, be sure to search with keywords like ‘remote’. Many job postings won't actually list ‘remote’ as the location, instead using that as a space for the location of their head office.

Tips for standing out in a remote job application

As more people catch on to the benefits of remote work, a big wide world of possibility is now open to you, and you don't have to be limited to geography to find your dream job or make your next career move. But that's the thing, isn't it? You and everyone else is thinking the exact same thing, and all of a sudden, instead of competing with a small circle of people, you're competing with everyone else in the world. So applying for a remote job isn't really the same as applying for an in-office job.

There are other things that remote hiring managers are often looking for, as signals of whether or not you'll thrive in a remote work environment. While they can take chances (I certainly have when I was on the hiring side), what will help you stand out is being someone who they can identify as being able to hit the ground running, especially if they're remote-first and have been able to spot patterns from their own teams on who was successful and effective and who wasn't.

So here are some of my best tips for landing a remote job:

• Pay attention to your writing. Can you write professionally but with a degree of emotional intelligence? Does that come through in your cover letter? Do you sound authentic and like you? These can be cues that go beyond ‘double-check your spelling and grammar’ that can give you an advantage with remote hiring managers that will be looking for signs that you can communicate confidently and warmly in a text-based environment.

• Have you managed projects? Put that front and center, even if you're not applying for a project management role. Successful remote teams are built on effective processes, and if you've managed and executed on projects, that's a signal that you're organized, can execute, and are self sufficient. This definitely includes side and personal projects too, by the way.

• Quantify your soft skills. Soft skills are the edge almost no one knows how to sell on a resume. It's not enough to stuff your resume with keywords like ‘organized’. That's literally what everyone else is doing. Is there any way you can link specific outcomes or metrics to your soft skills? Want to demonstrate that you have management skills? What outcomes and metrics tie into that?

• If you've worked remotely before or at a startup, mention it! You can insert it into your cover letter as well as in your resume, either in parentheses after your title or in lieu of the city. An underutilized way to demonstrate your impact outside of the bullet points on your resume, especially if you've worked at startups, is to add a one-liner to TL;DR the company and your contribution. This works very well if the companies you've worked at aren't big, super recognizable names. You can still stand out; you just have to be explicit about it. Walk them through, in bite-sized pieces.

• Mention tools and programs in your resume. We don't have a lot of space on resumes and not a lot of time to go through them, so it's hard to tell what you should keep and what you should leave out. Definitely take a look through the job posting and elsewhere on the company's website to see if they mention what tools and programs they use. If you've used them too, prioritize those even above the industry standard software (which, chances are: they'll assume you know – you'll still have these below, but you'll really catch their attention if you're already familiar with the tools and systems they're using across the company). This includes more abstract things like approaches, for lack of a better umbrella term, that are important to companies (for example, do they talk a lot about product-led growth or agile development?). 

This could matter more in the long run than making another tweak to your website.

And, we made it! Good luck on your remote work journey. You, just like many others, are just at the very start of a long road to a new way of working, where it's maybe not easier, but where we can perhaps all get exactly what we need and what we're looking for. And wasn't that the dream all along?