TL;DR: The bigest problem is standing out. How do you do it?
This is going to be a response to How I failed landing a remote position, a post in which its author describes how he failed to land a remote job. In this blog post I want to explain how to land it. I've been working remotely for the last six years and during that time I've landed ten remote jobs. I've had my ups and downs in a turbulent world of remote working.
The biggest failure was probably going on a trip to Singapore for an onboarding process where I quitted that job and returned home after just three days, but that's a story for another blog post.
It took me two months to land the last remote job and I've sent around fifty emails in total over that period. I also suck at technical interviews, so all the jobs I've landed required no technical interview. We agreed that the best technical interview would be to hire me for a test period of one month. I once failed that too. They required detailed reports on what I was doing and I thought that was redundant given the long descriptions in my commit messages and pull requests, so they decided not to give me another contract.
This brings me to another failure, called Toptal. As I said, I really suck at technical interviews. Things were different this time, though. I've prepared this time, went through some algorithmic exercises and all. The Ruby was against me this time, though. Somehow File.read wasn't working for me, so the interviewer even allowed me to go to StackOverflow. After I figured how to do it with IO there was too little time left. Hence I failed the technical interview again.
My first recommendation for remote jobs would be, you guessed it, Toptal. When you survive their algorithmic technical interview, you get an agent that connects you with the clients and whose job is to find you a job you'd be happy with. They take provision, of course, but the rate you end up with is still decent.
If technical interviews are not your thing, there are still plenty of sites to choose from. Behold Upwork! Just kidding, avoid it like the plague. Really tons of low quality clients and contractors there. I was very lucky finding my best client there (hi Gary!). You'll probably waste a lot of time on a quest of finding your perfect client in that kind of environment, so don't do it.
As mentioned in the original post, WeWorkRemotely is a great place to look for jobs, because you get some monetary filtering/quality control. At least they are wiling to invest that $299 to find their perfect candidate. I've got some decent responses there.
StackOverflow Carrers is also a good place to look with that remote filter turned on. I've got some responses there. It might be harder to get response from there if you don't have a decent reputation on StackOverflow.
Other than these three, I don't have anything to recommend.
Avoid angel.co, because jobs out there look outdated and I only received a single response from there for a position that turned out not to be remote after all.
Focus on those three sites and don't bother with the rest.
What matters is how you stand out.
I strongly discourage you from sending one email over and over again, like in the original post. It sounds like a perfect pick up line. It's something you think works, but in reality everyone knows you're using it over and over again. If it takes two minutes of your time to send an email, do you think someone will spend five minutes of their time reading it?
Take your time to write that email every time you apply for a job. Be as brief as possible, no one likes reading long emails, especially when there are hundreds of applications.
On to the most important part. How do you stand out among hundreds of applicants? The remote job market is very competitive, how do you convince your perfect client to hire you and not someone else?
I think the answer is building products and doing open source. My biggest advantage when searching for Rails jobs is the fact that I am a Rails contributor. That doesn't help with Node jobs, though. Believe me, I have tried.
I've spent half a year in 2014 trying to convert to Node and find a decent job in that market. Turns out no one cares about Rails contributors when searching for Node people. Who would've guessed!?
It's a much easier task to find a Rails job, though.
The less important part is the CV. I think it should be a mere formality and up to two pages long with a list of former jobs with brief descriptions. You can take a look at my resume for an example of this.
To conclude, the bigest problem is standing out. How do you do it?
How do you find time for all of this? Work less or work on weekends and late afternoons. Prioritize!