Note: I just created a free 7-day email course that shows you how to land a remote job in even further detail than this post. You can sign up for it here.
The steps in this guide are the exact same ones I followed to land a full-time remote job in less than 20 days. And during that time, I only spent 1-2 hours a day finding jobs and applying to them. If you dedicate more time, I’m sure you can land one even faster.
Having worked remotely for the past few months, I can say with full confidence that this is the way to work. Working remotely is the workforce, evolved.
In this guide I’ll show you how to join that workforce.
I’ll show you how to build a professional website, how to design a resume that hiring managers love, and how to effectively apply to jobs using the best remote job boards. Then I’ll wrap up by showing you the awesome door remote work opened for me. (Hint: It has to do with traveling the world with a great group of people.)
Every step is laid out clearly in this guide. All you have to do is want it and follow along.
Update: Shortly after publishing this, Naval Ravikant, the CEO of AngelList, shared this guide with his Twitter audience and my inbox was flooded with emails from people asking more about how to enter the remote workforce. If you want personal advice, feel free to send me an email at email@example.com.
“Technically a job board but it brought so many interview leads that I separate it from the others listed below.” https://t.co/BBYdpVJQ3O
— Naval Ravikant (@naval) November 28, 2016
Table of Contents
Part 1: Determine if Remote Work is For You
Part 2: Build a Professional Website
Part 3: Build the Best Resume of Your Life
Part 4: Apply to Remote Positions
Part 5: Seize New Opportunities
Part 1: Determine if Remote Work is for You
Before working remotely there are some things you should know. I’m going to share my story and some pointers.
Cubicles, Classrooms, Cages
For me, remote work is better than traditional work in nearly every way. It discourages micro-management, encourages success to be measured on results rather than hours worked, and, if you want, lets you travel the world with stability.
This is what I realized after persuading the company I worked for from 2014 to 2016 to let me give working remotely a shot. Convincing them took some time but it was definitely worth the effort.
After being relinquished from the hold of an office, I felt freer, healthier, and way more productive. I had the opportunity to move wherever I wanted and work however I wanted.
Even though our office was a fun place to work (doggies and friends all over in beautiful SoCal), offices just never felt right to me. They feel like classrooms and I never liked classrooms. I attribute them to harsh fluorescent lighting, enclosing walls, and rules.
For some people the traditional work environment suits them just fine. It makes them feel safe and secure and keeps them on track. But for me, going to the office every day makes me complacent. And because I like to constantly explore and invent, the more complacent I am, the more caged I feel.
That said, if you like going to the same office every day, in the same city, and like seeing the same people, remote work might not be for you. But if you’re in the office, always wishing there was something more, somewhere else you could be, I recommend giving remote work a shot.
Working Remotely Doesn’t Solve Working Woes
The last company I worked for let me work remotely but the mission and vision of the company became less meaningful to me over the years.
This doesn’t mean it wasn’t a good company to work for. It just means it wasn’t the company I should have been working for. They also didn’t have a remote work culture, which is very important.
The point is: Working remotely doesn’t get rid of issues you have with a company, nor does it add meaning to your work. You can distance yourself from a company but you can’t distance yourself from the underlying problems.
Whether you’re in the office or 5,000 miles away, the issues stick with you. So don’t just apply to any company that lets you work remotely. Instead try to find one that has a mission, vision, and product that’s meaningful to you.
I realize it’s often hard to be picky because of financial urgency, but if you have the luxury, take some extra time to dig deeper for that gold of a company. And if you’re working full time and have some money saved up, quit your current job and focus full time on finding a new one with a remote culture.
It’s scary but the right move. It’s what I did for this project: I traded my $65,000/year job with benefits for unemployment to focus full time on this. And it worked.
The Importance of Remote Culture
The company I left didn’t have a remote culture. As a remote worker I was an exception and I paid for that.
For instance, because I worked remotely I was often left out of conversations, projects, and events that other employees were involved in. If the company had a remote culture, tools like Slack and Highfive would help alleviate the issue. But without a remote culture these tools don’t do much.
The point here is to find a company where you aren’t the exception as a remote worker. Make sure the company is purely remote or has processes in place that makes remote workers blend seamlessly into existing workflows.
Below in Step 3 I’ll show you job boards that post remote-only jobs, so finding a company with a remote culture won’t be a problem.
Just be sure to ask how much of the company is made of remote workers. You do not want to be the guinea pig like I was. But then again, if it’s a cool job, maybe you won’t mind. There are always exceptions.
Note: The following steps assume that your specialty accommodates working remotely. If you can do most of your work from a computer, there’s a good chance there’s a company with a remote culture that is hiring for your specialty.
Part 2: Build a Professional Website
Having a professional website offers instant and profound supporting evidence that you have what it takes to work remotely. In addition to showing companies you have enough digital savvy to maintain your own website, a website also offers a platform where you can expound on points in your resume.
Within your resume you can:
- Link to pages that showcase testimonials and samples of your work (I’ll show you how to create these pages below)
- Link to an infographic version of your resume
- Show off your website address in your resume
- Show up in search results for hiring managers who Google “remote [your position]”
Create a WordPress Site
I already created an extensive guide about creating a self-hosted WordPress site. Following this guide will take you a few hours – maybe even a full day if you aren’t computer savvy – but it’s definitely the best way to create a professional website.
If you’d rather not traverse the somewhat-technical terrain of building a self-hosted website, you can create a free website on WordPress.com.
Note: If you need help with any of this, go ahead and leave a comment in this post and I’ll help you out.
After you create your WordPress site, move to the next step.
Create Showcase Pages
A solid one-page resume only offers room for 4-6 bullet points about your accomplishments at a company.
Showcase pages are pages on your site that give you the opportunity to elaborate on your accomplishments and show off specific examples of your work. You can link to showcase pages on your resume to increase the time hiring managers spend on your resume rather than someone else’s.
For instance, in this resume of mine, I link to a showcase page below the bullet points for each company. When the hiring manager clicks on Learn more, they are directed to the showcase page. (I’ll show you how to create a resume like this below.)
While you can design a showcase page in any number of ways, I believe that only four sections are needed to capture the interest of hiring managers and have them respond to your application.
The four sections your showcase page should have include:
- Overview of the company, your role, and your contributions
- Highlights of your accomplishments (in addition to those included on your resume)
- Examples of your work
- Testimonial from someone you worked with, ideally your manager
Assuming you created a WordPress site, creating a showcase page is very easy. In your WordPress dashboard, select Pages > Add New in the left sidebar to create a new page. Then use these examples of mine (first example, second example) to help you build your own showcase pages.
Create a Strong Homepage
Everything you add to your resume and homepage should have one goal behind it: To compel hiring managers to respond positively to your application in the shortest amount of time.
To quickly inspire action on your homepage include these four things:
- A picture of yourself (builds trust)
- 1-2 paragraphs about your specific area of expertise (builds confidence)
- 1 paragraph about your interests outside of work (shows versatility)
- 1 paragraph about what people should do next (inspires action)
You can check out my homepage to see how everything works together.
In the first paragraphs you’ll notice how I’m ultra-specific about my area of expertise. I don’t simply say I’m a content marketer. Instead I say I’m a content marketer who does something very specific – develops content initiatives for startups that build and ship web-based services.
This degree of specificity confuses some hiring managers but resonates with those who work at companies that you’d be a good fit for – and this is ultimately who you want to attract. They already understand the value you offer and will be better to work with because of that.
You should also mention your love for travel. Doing this shows hiring managers that you have a personality that thrives in a remote work environment.
Other things you can add to your homepage include:
- Links to content that explains what you do (in my first paragraph)
- Links to your showcase pages (in my second paragraph)
- Links to projects and outside interests (in my third paragraph)
- Link to your resume (in my fourth paragraph)
Part 3: Build the Best Resume of Your Life
At this point you should have a website, a standout homepage, and a showcase page or two. These online resources will prove to be powerful in convincing hiring managers that you’re suited for the job. But first we need to grab their initial interest. This is the mission of the resume.
Create the Content
Because the human attention span is short – especially for hiring managers who have the rote task of reviewing one resume after another – you need to make your resume short and sweet.
Keep your resume to one page and fill it with actionable words, hard facts (numbers and stats), and empathy. Don’t focus on why you’re applying. Focus on making them feel confident in hiring you.
While there are many differentiators between a good and bad resume, a post by USA Today covers ten ways to get your resume on the short list. I’m so glad this post was written because it covers the same best practices I’ve been following for years to win some great jobs.
The post breaks down best practices in terms of DOs and DON’Ts:
DO this in your resume:
- Make your summary or career objective employer-centric
- Talk results
- Lead with action words
- Be a quick read
- Get a little creative in terms of format
DO NOT do this in your resume:
- Don’t hide important information at the end
- Don’t overstate your value
- Don’t have typos
- Don’t talk in generalities
- Don’t be bland
You can see these best practices in action by checking out the basic version of my resume.
After taking a few minutes to review it, create the text for your own resume. Just focus on hitting all of the 10 points mentioned above and don’t worry about layout or design. We’ll cover that next.
Design with VisualCV
Hiring a designer to pretty up your resume isn’t cheap. It can cost a few hundred dollars, even more if you need something very custom. But because we don’t need anything custom – just something that looks better than every other applicants’ – using a web-based design tool is the best option.
After some research, the best solution I found is a platform called VisualCV.
In addition to offering an affordable monthly service, VisualCV designs your first resume for you for free and returns it within 24 hours of you signing up. They did this for me and I was very pleased with the result.
You’ll notice that the VisualCV template is more vibrant and engaging than the black and white document. The VisualCV templates also utilize space better. This allowed me to add a more cohesive summary, a testimonials section, and a skill-ranking barset – all on one page!
Here is some other stuff VisualCV offers:
- 17+ professional templates that are easy to customize with the VisualCV web application
- Analytics that show how many times your resume was viewed and downloaded
- Analytics that show which city your resume was viewed and downloaded from
- An online version like this and PDF version of your resume
- Free support for help designing your resume
My resume really made an impression on hiring managers. Many of those who replied back to my application made a point to say how much they loved it.
After designing a resume you’re happy with, move on to the next step. It’s time to lure and hook.
Part 4: Apply to Remote Positions
Ten years ago, wanting to work for a company with a remote culture would have severely limited your options. That isn’t the case today. Even though there are still more companies with traditional working cultures than remote ones, there’s no shortage of the latter. There’s also no shortage of ways to find them and apply to them.
Understand Today’s Best Practices
Applying to a job today is different than how it was two years ago. And it’s very different than how it was five, ten, or 15 years ago. The basics are the same – attaching your resume, conveying interest, and answering questions – but there are a few differences.
Generally the application process is less formal. For instance, no longer do you need a traditional cover letter. Hiring managers are more engaged by a short message that explains why you love the company and what you can do for it.
Below I’ll talk about this and a few other things I learned:
- Only apply to jobs you’re passionate about. If you don’t, you’re wasting your time. In a few months you’ll just end up reading this guide again. Take your time, be picky, and do it right the first time.
- Create a progress tracking sheet. You will probably apply to 50 positions or more, making it hard to keep track of everything. A progress tracking sheet for your applications will help you keep everything organized. You can model yours off of mine.
- Don’t use a formal cover letter. If a job requires a cover letter, definitely include one – but make it custom. After taking 10 minutes to read the full job description, check out the company’s website. Then create an authentic message. It can consist of two paragraphs or 10 bullet points – as long as it gets your passion and skills across.
- Link to stuff in your cover letter. Even if you aren’t asked to link to samples of your work, do so anyways. Also link to your showcase pages and a post like this that elaborates on why you’re applying to new jobs. This will engage hiring managers and give them an opportunity to spend more time on you – not the other applicants.
- Take your time on screening questions. The company that hired me decided to give me an interview because of how thorough my answers were to their pre-interview questions. (You can view them here.) I’m not guessing this either. Dave Nevogt, the CEO of Hubstaff who hired me, told me this about my answers:
“This was a big part of capturing my interest. Give before you get, and by stating that you spent some time on the application it captured my interest and I looked further. Plus you have specific examples of the successes you’ve had and spoke in terms of the end result which is great.
“I had about 450 people apply that could write well, but that’s not what I was looking for. I was looking for an end result, so speaking to those in your summary went a long way with me.”
Now that you have a good idea about how to apply, let’s start the really fun part – applying…
Apply Through Various Channels
The way we apply to jobs is changing. Before the Internet, if you wanted to apply to a non-local company you sent them your resume by mail. And once the Internet started becoming commonplace for job postings, you went to a general job search site like Monster and applied there.
You can still use both of these methods but they are very inefficient – especially for applying to jobs with remote work cultures.
A better way to apply is to through ultra-specific job boards that publish remote-only work. You can also apply to companies with the best remote working cultures – even if they don’t have a job listing.
During my job search I tried different application methods and all of them got me at least one job lead. Below I’ll describe how each one works.
This is technically a job board but it brought me in so many interview leads that I have to separate it from the others listed below. It’s so good that, when I discovered it, I was genuinely surprised that I didn’t know about it sooner – and I don’t get surprised easily.
This place is gold if you’re looking for a job at a startup. After you spend some time filling out your profile (here’s mine), applying is incredibly easy.
When I was looking for remote content marketing gigs at startups, @AngelList was the worst kept secret from me. That job board is gold.
— Robert Gibb (@gibbiv) November 24, 2016
Here is how applying on Angel List works:
- After creating and completing your profile, go to the job board.
- In the search bar at the top, type your ideal title (for me “content marketer”), then hit Enter.
- In the Job Type dropdown, select Full Time and Contract and Remote OK. (Some contracts are full time, which is why I recommend selecting it. In fact, the gig I ended up landing was a contract role.)
- In the Compensation dropdown, drag the cursor for Salary to the lowest annual salary you’re willing to make. At this point your search should look something like this:
- Below the search and filter section a number of startups will be listed. (If none are listed, tweak your filters.) Above the first listed startup you will see two options:
After reading the job description and visiting the startup’s website, select the No, Skip option if you are not interested. If you are interested, click the pencil next to the Yes, I’m Interested option.
- If you are interested in the job, after clicking the pencil add a short message to the company in the message box that appears. Convey your interest in that specific company and tell them what you can bring to the table. Here is an example:
Then hit Send, and it’s as easy as that.
If the startup is interested in you, you will receive a notification via email. You can then set up an interview.
Remote Job Boards
Due to the rise of companies with remote working cultures, there’s now a demand for ways to find these companies. In addition to Angel List, the job board sites below have answered this demand.
These job boards are usually run by a small or large team that curate job openings by remote companies. The boards with the smaller teams usually offer their service for free while those with larger teams require a monthly payment (usually $15 per month).
Because these all of these teams are focused on curating remote jobs, there’s usually some overlap. However, it’s not to the point where every job board has the exact same positions, so check them all out.
- We Work Remotely mostly posts positions for programmers, system administrators, customer support engineers, marketers and designers. While it doesn’t post as many positions as other boards, the quality of the jobs posted is very high.
- Working Nomads focuses on jobs for developers. There are a few postings for other professions, but don’t spend too much time here if you’re not a developer.
- Remotive is good for a quick browse. If you’re not a developer there aren’t too many postings, but, like We Work Remotely, the jobs are at companies with the best remote work cultures.
- Jobspresso probably has the best job filtering system. You can also post your resume there if you want hiring managers to reach out to you. I didn’t do this myself but it doesn’t hurt.
- FlexJobs is $14.95 per month and I was skeptical at first. However, because it’s a paid service, FlexJobs has the resources to employ people that constantly scour the web for telecommuting jobs. While the quality of the jobs varies, the amount of jobs listed is great. There is something here for everyone.
Other Job Boards
Each of these boards has a cool “quick apply” feature. This means you upload your resume once and can apply in one click to a handful of companies – no cover letter required.
To find remote opportunities on these boards, use the keyword search field at the top of the site and leave the location field blank. After typing in a keyword related to your profession, add the word “remote” to the end of the query.
For instance, because I am a content marketer, I would type “content marketer remote” in the keyword field, then hit Enter.
Before applying to the job, make sure to do a search for the word “remote” in the job listing. To search the page for this word, press Ctrl+F or Command+F depending on whether you’re using a Windows or Mac. When you locate the word “remote,” make sure it relates to the company hiring remotely.
Straight to the Source
Going straight to the source means going to the companies with the best remote work cultures. You can find these companies by doing a simple Google search for “best remote companies.”
I personally like this list and this other list by Cloudpeeps the most. I reached out to about 15 of 20 companies mentioned in these posts – even when they didn’t have relevant job openings – and about a third replied to me.
Sometimes I would send them a tweet asking them if they were hiring if I couldn’t find their job page. The worst that can happen by sending a tweet is no response at all or a kind reply like this:
@gibbiv Thanks! We don’t have any openings at the moment. Best of luck with the job hunt ✌️
— DHH (@dhh) November 8, 2016
Note: In your tweet, add your resume as an image.
At best they can open up a great opportunity. For instance, after sending a direct message to the startup 1Password on Twitter, someone on their team replied to me, saying to send my resume and letter of interest to the email address responsible for jobs.
This got him excited and landed me an opportunity to prove my skills with a test project.
Yes – reaching out to companies without job openings is untraditional. But it’s definitely worth your time if the company has a product you believe in and is known for having a great remote work culture.
Part 5: Seize New Opportunities
Now that you have that sweet remote job, do things you didn’t do before!
Smile more, use gas for weekend trips, spend more time with those you love, work from your favorite cafe, work from your favorite chair at home, work out back on your deck – or do what I’m going to do and travel the world.
You now have so many more choices than you did before, so choose wisely.
Travel the World
You can travel the world on your own, or you can do it with a group of people. You can try to meet passionate, open minded people along the way, or you can travel with them from the start. And you can make all the travel arrangements yourself, or you can have someone else do it for you.
I chose to do the latter in every case. And this didn’t mean I had to find people, make sure they weren’t psychopaths, organize the group, then find a travel agent.
Today there are work-and-travel programs that do all of this for you. They bring the best remote workers together and organize travel plans from one city to the next. They also take care of booking the apartments, coworking spaces, and events in every city you visit.
There are many programs like this. Some focus on short term travel while others coordinate worldwide trips that last one full year. I ended up choosing the year long option.
Below are some short- and long-term programs that Katelyn Smith at The Remote Nomad recommends.
These programs cost a good bit of money, but when you consider what you’re getting, the price is more than fair. It’s hard to put a price tag on a year of travel, especially when you don’t have to worry about anything – from booking rooms and office space to finding new friends.
- Remote Experience: You can choose to travel with the group for four, eight, or 12 months. The down payment is $3,000 and the monthly payment is $1,750.
- Remote Year: The length of the program is one full year. The down payment is $5,000 and the monthly payment is $2,000 – except for the final month. The total cost is $27,000.
- We Roam: You can choose to travel with the group for six months or a full year. The full year option is the same price as Remote Year.
This is the program I chose. After speaking with We Roam’s co-founder Nathan Yates, it seemed the most authentic to me. And after signing up, the pre-trip experience has been seamlessly executed by We Roam’s travel and operations manager Blaine Anderson. I’m stoked about this trip and look forward to writing more about it.
These programs seem great if you want to get your feet wet as a digital nomad but don’t want to commit yourself to a half or full year of travel.
- Hacker Paradise: You can stay with the group for two weeks to three months and the cost ranges from $500 to $1,980 per month.
- Co-Work Paradise: The length of this program is one month and takes place exclusively in Bali, Indonesia. It costs around $3,000 but there is a lot of cool stuff included.
- WiFi Tribe: There is no limited length to this program but there’s a minimum length of one month. You can stay with the group one month, then keep traveling with them. I’m not sure how much it costs but I spoke to them and they seem like awesome people.
- Roam: You can stay with the group for a week, a month, or longer. Pricing starts at $500 per week.
Prepare for the future of work
The co-founders of Basecamp — a 100% remote tech company — have written an awesome book called Remote: Office Not Required about how to work effectively from home and why remote work beats the office every time.
You can pick it up on Amazon here.