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How To Overcome the Hardest Parts Of Landing a Remote Job




Remote Job Hunting



Some weeks ago, we asked you what the hardest parts about landing a remote job were in our Twitter and Instagram accounts. We got A LOT of replies and now, we’re sharing the best answers to your 10 toughest challenges:


What are the biggest challenges you’re facing in your quest to land a remote job that you love?

We recently posed this question to our awesome We Work Remotely Community and heard a ton of varying responses.

You may be struggling with some of these obstacles yourself. Or maybe you haven’t encountered them yet, but would appreciate the heads up on how to handle them if you do.

We totally get it. Job hunting depression is real, and the process can be super stressful -- especially if this is your first time on a remote job search.

So today, we’re going to answer the top 10 frequently asked questions about landing a remote job and help you create a winning game plan to hurdle these difficulties without breaking a sweat. 

FAQ: How To Overcome the Hardest Parts Of Landing a Remote Job

Since one article can’t cover all these challenges in the detail they require, we’ll share a brief overview of each question/issue. Then we’ll either supply an answer or share a resource where you can learn more.

The goal is to give you a few ideas on how to solve these problems, so you can create a strategy that breaks down these obstacles into smaller, more manageable tasks to knock out with ease.

So here are the top 10 most frequently asked questions about landing a remote job:


1. How Do I Find Remote Jobs that Hire Where I Live (Even If It’s Outside the US)?

The number one frustration we heard about landing a remote job was how to find companies hiring virtual candidates outside the US and Canada. And we’ll admit, it can be tricky.

See, there are loads of rules and regulations regarding hiring overseas employees as a US-based company. So it’s often easier for American companies to simply hire remote candidates from The States.

However, don’t get discouraged! There are a few ways to get around this:

Check the top global companies first. Google, Microsoft, Twitter -- these companies are known all around the world. And many companies of this caliber are now allowing remote work. Head over to their career portals, and see if they have remote listings in your field or industry.

You can use these resources as a jumping-off point for your search:


Make keywords work for you. Search engines may lead you to remote positions you may have never stumbled upon organically. But that’s only if you use the right combination of keywords to unlock them.

In our guide on How To Find Remote Jobs So You Can Finally Ditch Your Commute and Cubicle, we outlined exactly how to create this powerful keyword list.

Essentially, you’ll want to jot down:
  • Whether you’d like to work full or part-time
  • What type of company you’d like to work for
  • Job titles, positions, or roles you’re searching for 
  • Education, skills, and certifications you have


Then, add in specific keywords that will bring up remote positions only, such as:
  • Remote
  • Virtual
  • Telecommute
  • Work from home / work at home
  • 100% remote / 100% distributed 
  • Fully remote / Completely distributed

The last few keywords on that list mean a company doesn’t have a main office anywhere, so all employees work remotely around the world. But you could also add in your specific country as a keyword to pull up listings from organizations operating locally.

Combine these terms, and you may wind up with a search like 100% Remote Software Engineer CSSLP certification Poland. 

Come up with a few variations on your keyword list to cover all your bases, and see what comes up!


2. How Do I Know What’s a Scam and What’s a Legit Remote Job Posting?

Thanks to the rise in remote work during COVID-19, there’s been an equal increase in job scams. These fake opportunities often sound too good to be true (because they are) and leave unsuspecting, hopeful job seekers open to cybercrimes like identity theft.

So check out this post on How To Tell a Legitimate Remote Job from a Scam to learn seven ways to spot a phony job listing and five tips to find real work-at-home roles.


3. What’s the Best Way To Narrow My Scope and Find My Ideal Remote Job?

Our guide covering How to Find a Remote Job That’s Right For You outlined four steps to finding your dream gig. The first is knowing how you work best. 

Next, you’ll need to dig deep to discover what you’re good at and what you actually like doing -- which aren’t always the same. 

So it’s smart to come up with a list of potential roles and then read through the job duties and responsibilities posted in job ads for them. 

Need some direction? Start by weeding through a general list like:


Look for specific tasks you’d enjoy performing daily and note which duties you’re not crazy about. Then use these criteria to find remote jobs matching your must-have and must-avoid lists.


4. Do I Have Enough Experience To Land a Remote Position?

You may be surprised to learn that you can impress hiring managers at remote companies without ever having worked remotely before. Why? Because many of the skills you’ve perfected in an office position translate to the remote work world.

You just need to frame these abilities in a way that would benefit a remote employer. You’ll find a few tips on how to do this in these two guides:



However, you should also consider skilling up to invest in yourself. Every new ability you pick up makes you a more qualified, well-rounded candidate companies will want to snatch up ASAP. That’s why personal development catapults your remote career.

So consider learning:


Get yourself familiar with the most commonly used remote work tools and processes, and you’ll give hiring teams confidence in your ability to get the job done despite your lack of telecommuting experience.


5. What’s the Secret To Beating the ATS?

Applicant tracking systems (ATS) could be one of the biggest reasons you’re not landing that online interview. Companies use this software to scan resumes for specific keywords, job titles, certifications, and more. 

If your resume passes this initial parsing, your job search documents might make it to a hiring manager’s inbox. Then they’ll see how qualified you are for the role. But if you fail the ATS test, your application may wind up in the trash, never to be read.

These guides will ensure you make it past the ATS gatekeepers and beeline straight to the interview pile:


Once you know what the algorithms are looking for, you’ll have no trouble outsmarting them. 


6. How Can I Stand Out From the Competition?

Competition for remote roles has never been higher. So once you find a position you’re interested in, you’ll need to show hiring managers what makes you different (and better) than all the other candidates vying for the role. To do that:

Learn how to tailor your resume to your dream remote job. Hiring teams know when someone’s reusing the same resume and cover letter for every job they apply to. Customize your resume for each position, and you’ll have a better chance of proving you’re the perfect fit.

Build a remote job portfolio to stand out online. Add a link to your personal website to show off your skills to hiring managers. They’ll have a first-hand look at what you’re capable of and why you’re unique and memorable.


Use a bold, eye-catching resume that commands attention rather than puts hiring teams to sleep. There are tons of sites for modern, free resume templates you can easily customize for your work history, skills, and aesthetics.  

Find a career coach that’s best matched for you. They may be able to highlight traits or abilities people in your industry are specifically looking for, and you possess. Use their insider knowledge to give hiring teams precisely what they’re seeking. 


7. How Long Does the Remote Interview Process Take? How Long Will It Take to Land a Remote Job?

According to the US Bureau of Labor Statistics (BLS), 28.7% of unemployed Americans found a job in less than five weeks (as of September 2021). But it took a staggering 47% to land employment in 15 weeks or longer [*].

Now, keep in mind that this data reflects the entire job-seeking population, not just those who only applied for remote work. So take those figures with a grain of salt.

Truth be told, remote job hiring is a much faster process. Utilizing ATS, virtual interviews, and strategic job board partnerships helps remote employers connect with qualified candidates in less time.

Still, there are a few simple yet effective tips to strengthen your remote job search and hear back sooner, such as:

  • Following up. Hiring teams are super busy, and sometimes they don’t have time to get in touch with promising candidates. So after you send a company your resume, shoot over a quick follow-up a few days later. Someone may pull up your resume to reply and decide you’re actually fit for an interview.

  • Asking when you should expect to hear back. If you make it to the interview round, see if you can get a timeframe for when the company will be completing their other interviews and be ready to make a decision.

  • Sending a thank-you note one day after each interview. This helps you stay top-of-mind with hiring teams and shows you’re serious about the position. Companies will be impressed and eager to get back to you.

While these proactive steps may not speed up the process, they come off way better than taking a set-it-and-forget-it approach to potential employers.


8. How Will I Know Whether a Remote Organization Has the Best Company Culture For Me?

Company culture is defined as the values, mission, and practices shared by an organization and its employees. These guiding principles dictate everything from how employees speak to each other to where the company sees itself in five years.

Some people think it’s easy to gauge the vibe of a company when you walk into their offices for an interview. But you can tell a lot about a remote company’s culture if you know where to look.

To see if an organization’s company culture meshes with your goals and values:


Follow these tips, and listen to your intuition. You’ll immediately feel it in your gut when you’ve found your potential tribe.


9. Will I Do Okay In a Remote Position?

How will you know if you like remote work if you’ve never done it before? Unfortunately, we can’t give you an easy answer here. But we can help you kick off some deep, productive soul-searching to help you decide.

To learn if the remote workplace will suit you, check out:



And to set yourself up for remote work success, read up on:


Use the advice in those guides to score a more complete picture of your potential life in the virtual workplace.

10. Where’s the Best Place To Look for Legit Remote Jobs?

This is the easiest question to answer on today’s list: it’s We Work Remotely!

WWR is the largest remote work community in the world and the number one destination to find incredible, legit remote jobs all over the globe. Some of the biggest companies trust our remote job board to list their work from home positions, such as Google, Amazon, Basecamp, and more. 

Unlike traditional online job boards that only post a handful of remote opportunities, our remote job board focuses exclusively on telecommuting roles.

Plus, we make it easy to see where remote employers are hiring. Our job listings will let you know whether a remote company’s seeking US-based candidates or teammates living in Europe, Asia, Canada, or anywhere in the world.



So make We Work Remotely your first and only destination during your remote job search, and you may have more luck overcoming some of the hardest parts about landing a virtual role.

Check out the We Work Remotely Learning Portal too! You’ll find even more tips on how to score your dream remote job and thrive in your new career. 

We believe in you -- you’ve got this!


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