How to get a full-time remote job [5-day challenge]

In 2017 I traveled to 12 countries in 7 months with We Roam and in 2016 I traveled all over the United States. These adventures were possible because I had a full-time remote job.

I want others to have opportunities like this, which is why I created this challenge. Over the next five days I’ll show you exactly what I do to land full-time remote jobs. (I’ve landed three in my career.)

Whether you want to travel, take care of an elderly or sick family member, or simply work for a company that trusts its employees enough to let them work remotely, this challenge is for you.

“I work with remote workers every day and have nevera seen anyone land a remote job as fast as Rob. If you want to work remotely, take this challenge.

Blaine Anderson, Travel and Operations @ We Roam

Table of contents

Day 1 – Finding your first three remote jobs 🌍
Organize your remote job search with a tracking sheet and add your first three jobs to it.

Day 2 – Sending ideas instead of cover letters ✉️
Spend a few extra minutes customizing your cover letter to 10x your invitations to interviews.

Day 3 – Creating a sexy resume that sells 💋
Create a web-based resume and structure it in a way that puts you on hiring managers’ shortlist.

Day 4 – Mastering the Tinder of remote job boards 🔥
“Swipe right” on remote positions you love and get cool startups to swipe right on you.

Day 5 – Leaving the interview with a job 💼
Learn the question you need to ask at the end of each interview to start a working relationship.


This challenge is for professionals who can complete 100% of their work from a computer. But this doesn’t mean you need a stereotypical remote profession. There are remote positions available for people who are not web developers, designers, and writers.

I’ve seen full-time remote positions in accounting, customer service, finance, human resources, marketing, project management, recruiting, and sales, to name a few.

If you’re going into the office just to work on your computer, I guarantee you there are remote job opportunities out there for you. You just need to know where to find them and how to apply to them.

I’ll show you how to do this over the next five days.

Action Step: Request to join the Facebook group for this course. After I approve you, introduce yourself to current and aspiring remote workers in this thread.


In my experience, it takes at least one month to land a full-time remote job. Based on this, you won’t land a remote job while taking this challenge. There’s just not enough time. But you can get started on the path to landing a remote job.

A strong first week of your remote job search means applying to 10 full-time remote positions. This will give you the momentum you need to get an interview as fast as possible. Throughout the challenge, I’ll keep you on track to achieve this with action steps.

You can also hold yourself accountable with this checklist I put together or with a service called stickK. This free service lets you put money on the line to motivate you to reach your goal (i.e. apply to 10 remote jobs).

Action step: Pick up the book Remote: Office Not Required if you haven’t already. In my opinion, it’s the best introduction to working remotely currently available and something you can easily read in 5 days while taking the challenge.

Remote Job Challenge

Day 1: Finding your first three remote jobs

Organize your job search

During your remote job search, you’ll apply to dozens, even hundreds of positions. To stay organized, you need an easy way to track jobs you apply to and the status of your applications. You can do this by creating a copy of the Google Sheet I use for my own remote job hunts.

Action Step: Make a copy of this Google Sheet to track your job search. To do this, select FileMake a copy after opening the Google Sheet. Name the sheet “Remote Job Tracking Sheet”.

Find three remote jobs today

In the video tutorial below, I show you how to find remote jobs on traditional job boards like Indeed and LinkedIn Jobs. I also introduce you to remote job boards that only post remote positions.

Do not apply to any jobs today though.

The purpose of this exercise is to show you that remote opportunities exist for your profession and get you excited about working remotely. You should only apply to the positions after I show you how to create an effective cover letter and resume.

Action step: Find three remote job listings and add them to your job tracking sheet. Then share your sheet in this thread of the Facebook group. To share, click Share in the top right part of the sheet, then click Get Shareable Link. Select the option that says Anyone with the link can comment, then click Done. Copy the link and add it to the Facebook thread.

If you find less than three open positions today, don’t worry. On Day 4 I’ll show you how to use a job board where well-funded startups post plenty of remote job opportunities. The reason I didn’t introduce you to it today is because there’s a special way to use it.

Written tutorial: You can view an extended version of this lesson in written form here.

Day 2: Sending ideas instead of cover letters

Hiring managers at remote companies don’t want a traditional 5-paragraph cover letter. They don’t care about who you are and what you’ve done. That’s what your resume is for. What they want is a sense of what you can do, for them.

As a marketer, when I lead with ideas about how I’d grow the company in my cover letter, I get more responses to my application than when I lead with a history of my experience and accomplishments.

I think there are two reasons for this. One, I give hiring managers something different than what they expect. Two, my ideas about the company show I took time to review what the company is doing.

This idea-first approach takes more time than sending a generic cover letter, but it’s more effective. The first company I applied to with this idea-first approach was a remote startup. The founder, who was also the hiring manager, responded to me over 250+ other applicants.

Idea first cover letter

You can view the email I sent to Austin here.

Admittedly, it’s too long. Austin should have only needed to read it once. But if you’re inspired, write away. I was excited about what the company was doing when applying and I think Austin felt this.

Here is template I use now. It’s shorter and more direct.

Action Step: Apply to a company you added to your job search sheet yesterday using this cover letter template. Spend at least 10 minutes generating ideas for how you could help the company. Attach a screenshot of the cover letter you send in this thread in the Facebook group.

Use your current resume when applying for now. Tomorrow we’ll create an online version of your resume that you can link to from your cover letter.

Written tutorial: You can view an extended version of this lesson in written form here. It suggests using a cover letter template that’s different than the template I recommend in this email but it’s just as effective.

Day 3: Creating a sexy resume that sells

To find an example of a resume format to avoid, I searched Google for “example of the perfect resume”. I know that many people’s idea of a perfect resume is misguided. My search proved me right. It took Google exactly 0.63 seconds to retrieve this “excellent resume,” part of an article by Business Insider.

This resume is far from excellent. It’s wordy and hard to skim, which is ironic because the article says that “recruiters spend an average of six seconds reviewing a resume before they make the initial decision.” In six seconds, they’re likely to decide they need another coffee.

Compare that resume to my resume that helped me land remote jobs at some really cool companies. It’s succinct and easy to skim, and every word and line has one goal: to sell the hiring manager on the idea that I’m worth interviewing.

This is the type of resume I’ll show you how to create today.

Make yourself sound sexy

My resume makes me sound better than I probably am, which is why it works. For instance, I didn’t directly help a startup I worked at get acquired, but on my resume I write “I helped the startup MaxCDN get acquired.” To a degree, this is true, and “to a degree” is all you need when coming up with accomplishments for your resume.

In the video below, I’ll show you how to hype yourself up in your resume to get hiring managers interested in interviewing you.

Action Step: Make a copy of this resume template (File > Make a copy) and fill out all the information.

Make yourself look sexy

Thanks to high school and college career counselors stuck in the past, the black and white resume is expected (but not enjoyed) by hiring managers, much like the 5-paragraph cover letter. Being aware of this expectation gives you a distinct advantage.

By giving hiring managers a resume that’s colorful, visual, and personable, it’s like giving them neapolitan ice cream when they’re expecting vanilla or chocolate. Whether it suits their palette or not, it’s memorable, which is what you want your resume to be.

In the video below, I’ll show you how to design a memorable resume with VisualCV.

Action Step: Create a VisualCV account. There’s a free and paid version of this service. The paid version lets you download a PDF version of your online resume, remove the VisualCV logo from your resume, and much more. It’s the best $36 you’ll spend this year. When you’re done, link to it in this thread of the Facebook Group.

With your new cover letter template and resume, you now have a fighting chance at landing interviews with remote jobs you’re interested in. Throughout the week, you’ll use them when applying to remote jobs.

Written tutorial: You can view an extended version of this lesson in written form here.

Day 4: Mastering the Tinder of remote job boards

AngelList is a place where early and late stage startups list open job positions and information about their funding rounds. Because working remotely is more accepted in the startup world, many companies on AngelList have remote positions.

AngelList works much like modern dating applications. You can choose to say “Yes, I’m Interested” or “No, Skip” to positions that match your job search criteria. If you match with a company, you’re introduced to the hiring manager through the website’s messaging platform. This direct connection makes it easy to set up an interview.

Where I went wrong with AngelList before was “swiping right too fast.” If you’re interested in a company, you need to send them a message. Clicking the “Yes, I’m Interested” button isn’t enough. For the message content, you can use your cover letter template or say what comes naturally. The latter works better if you’re applying to a startup that you really connect to.

In the video below, I’ll show you what kind of messages have worked for me, how to optimize your AngelList profile, how to search for jobs on AngelList, and much more.

Optimizing your AngelList profile

When applying to a remote job on AngelList, you’ll see the profile of the startup that posted the job and judge the startup based on what you see. That startup will do the same for you when they receive your application, so your profile better be good.

Because you already have a great resume, filling out your AngelList profile will be easy. It should only take you 15 minutes.

Action Step: Complete your AngelList profile and share it in this thread of the Facebook group. I give you some tips for filling out your profile in the video below.

Finding and applying to remote jobs on AngelList

AngelList is awesome because of its job filters. You can find startups interested in hiring remote workers worldwide, find startups with funding money that can afford to hire you, and filter positions by salary range and equity. AngelList also makes applying to jobs stupid simple: you just write a short message and send it.

In the video below, I’ll show you how to find remote startups willing to pay you what you’re worth and what to write to land an interview with them.

Action Step: Apply to 2 remote positions on AngelList and add them to your job tracking sheet.

At this point, you have the tools you need to get an interview for a remote job. But what do you do when you get the interview? Tomorrow I’ll tell ya.

Written tutorial: You can view an extended version of this lesson in written form here.

Day 5: Getting your foot in the door

I get most of my job opportunities through AngelList, which means I’m usually talking with a cofounder of a startup.

In the video below, I’ll tell you what I say at the end of the interview, and throughout the interview, to convince the cofounder that I’m the one. (Note: In the startup world, interviews are usually referred to as “chats”.)

And now for your final action step…

Action Step: Apply to 10 remote jobs by Sunday night and reply to your initial comment in this thread of the Facebook group when you do. I’ll be watching. 👀

If want to talk remote work with me and other people in the course, go post something in the Facebook group or hit me up on Twitter.

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