The 4 common mistakes of remote job seekers
3 min read

The 4 common mistakes of remote job seekers

Today, I'll share my learnings from speaking with hundreds of people who are actively looking for a remote job. I'm seeing the same mistakes repeated by many of them.


I'm Sergio Pereira, and this is the Remote Work newsletter 

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Last week I told you about my experience as a remote Fractional CTO, and how you can apply it to your own skills and experience.

Today, I'll share my learnings from speaking with hundreds of people who are actively looking for a remote job. I'm seeing the same mistakes repeated by many of them.

What's surprising is that for most of them, it's only when I point it out for them, that it becomes obvious they should do something different.

Let me break those down into 4 key mistakes, and how you can avoid them:

1/ Applying to just a few jobs

This is by far the biggest mistake I see. And it's a big surprise to me.

Back in 2016, when I got my first remote job that 5x'ed my salary, I applied to ~300 job opportunities. It was really hard work with several iterations. For a long time I assumed everyone had that level of hustle.

So it surprised me to learn that many people aren't doing that. Both in the Remote Jobs Braintrust and in my DMs I chat with people who say they are struggling in their remote job search. And I ask "How many job applications did you send last month?" - Some say 5, others say 10. Some say 1, and that's the only company they targeted.

Look, this is wrong. And it's wrong because remote jobs are competitive, and it's a very tight funnel from the applicant's perspective. It's a numbers game, you should apply to dozens, or even hundreds of jobs.

Lacking that volume, you can't even draw conclusions to iterate on. How can you tell that applying to Tech Lead roles doesn't work, if you applied only to 5 such jobs? See each job applications as an opportunity, but also as a data point. Volume matters, folks.

2/ Lacking a clear target role

When I ask "What role are you applying to?", some people reply with 10 different job titles.

There's nothing wrong with that. It's just that you think you're increasing your odds, by casting a wide net. But you're doing the opposite.

Let me tell you why. If you're applying to so many different roles, it's likely that you won't create a CV specific to each different role. Most people just create a generic CV and generic cover letter and generic application collateral.

They feel that generic will "fit any role". But they are wrong! Having such a generic positioning makes them a mediocre candidate for any role they apply. And they end up being ghosted in most of them.

3/ Not adapting their applications to each role

Your goal is to resonate as a "unique" candidate to each role you apply, so you can increase your odds of being selected for an interview.

Think about my case for a second, as a CTO who receives hundreds of applications for each role I open. I spend some 5-10 seconds looking at any CV, maximum. If I'm hiring for a Javascript role, I want immediate evidence that the candidate has such experience. And in a pool of hundreds (sometimes thousands) of applicants some candidates clearly show that, either in a few bullet points on the top, or in their last job section. Those are the candidates I select for interview.

So there's no other way around. Being generic means failure most of the times in this competitive landscape. You should apply to dozens (or hundreds) of job openings, and you should tweak your CV and application collateral for each of them. It's challenging, I know, but in the Remote Jobs Braintrust I show a few tactics I used to make such customisations at scale.

4/ Inconsistent personal brand between CV and Linkedin

The hiring manager spends some 5-10 seconds reviewing your CV. If you do a good job that gets them interested in spending another 30 seconds to confirm that first impression.

So they'll read a bit more of your CV, and they'll look you up on Linkedin. If all that continues to prove you're a good fit to the role, you'll be invited for an interview. That's what success looks like for any job application.

However, some people get tripped up here. Some candidates don't even have a Linkedin profile, and the recruiter would struggle to share their profile internally, they'll be backlogged. Some have a Linkedin profile that contradicts their CV in some way. Either the last job is different. Or the highlighted skills are different. Those things show recklessness or perhaps unethical behaviours, and when in doubt the hiring manager will discard those.

If you're looking for a new remote job, of if you're thinking this will be your New Year's resolution. Then you should join the Remote Jobs Braintrust. The January cohort will be tailored to Asian and European timezones, with live sessions at 11am UK time. Grab you seat here.

Thanks for reading this newsletter until the end. You can read all past editions here. Make sure to share it with your friends and colleagues so they can read it too.

See you next Friday,

Sergio Pereira, 
Startup CTO & Remote Work Lover

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