As someone who has hired many-a-folk into remote teams, I am often asked: "How do I get a remote job?". Many are inspired by the luxurious, jet-setting allure of the Digital Nomad. Others just want to break away from a commute, escape the drudgery of a typical 9-to-5, and be closer to their families. Whatever your reasons, I hope to help you remote-enable your journey through life.

Working with YC-based start-ups and a couple 'major' technical companies, I have welcomed many into the remote-working world. I have had postings glued to the top of 'Who is Hiring' within Hacker News, scaled a highly technical remote team from 22 to 77 in 7 months, and engage with some of the brightest souls around the world. Being most comfortable in the quiet mountains of cold-Canada, my work has almost exclusively taken place through screens, over vast distances.

I am pleased to share my thoughts and experiences with you so that you may find the freedom you seek in remote opportunities. I hope that you find value in these words.


New Fangled vs. Traditional: Seek The Progressive

An amiable character once told me: "I do not like resumés. They represent ritualized lying". Luckily, remote companies are stepping away from traditional resumé submission to try hiring processes that are more evidenced-based. Companies want to see how well you will do the work instead of how well you can tweak your presentation to appear as though you may be a good fit for the work. They want to know that you will be able to add value to the team.

Months prior, when scaling a technical team we applied a blind, work-sample based hiring process. Anyone was free to take our work sample - we did no pre-screening. Identifying information was stripped and the samples were graded on consistent and objective criteria. The samples were constructed to resemble the actual work. We could see how well the applicant would do the work and the applicant would see if they enjoyed doing the work.

The samples were difficult. We had a young individual, a student, crush one of our hardest engineering samples. He earned a six-figure job doing a coding exercise 'just for fun'. Speaking to him afterwards, he awkwardly confessed: "Erhm, I --... Well... I have never really had a job before". We laughed. It did not worry us in the slightest. We liked him and we knew he was talented and capable.

More and more companies are adopting variations of a 'show me' model. If you find these opportunities, relish them! If you are lacking experiences and find that you have no tantalizing 'major companies' like Google or Facebook as prior engagements, try to find opportunities to demonstrate your abilities. As a CEO amigo once said: "Having worked at Google only proves that you were fit for working at Google".

People seem to avoid work-sample based opportunities, fearing embarrassment and wasted time. You will never know until you try. Worst case: you get some practice and a sobering report on some of your abilities. Best case: you find opportunities far beyond your loftiest expectations.

How to Stand-Out? Remember The Humans

When building out remote teams, a person sits at the receiving end of a queue. While the job seeker reads the job ad, piqued by the remote-working promise, they send their hopes in the form of a resumé and a letter -- or, work sample grades. They are one of hundreds or thousands. Staring at the applicant queue, the hiring person sees a flood of names, experiences, spins, lies, and promises. How can you stand out in this torrential deluge of competitors?

Remember that a human will read your first contact. Never, ever send out a canned and impersonal applications. Regurgitated and inorganic letters are immediately apparent to the experienced eye. Learn as much as you can about the company and then tailor your communication to demonstrate an interest and general understanding of their market and their culture.

The best candidates have options. The most desirable candidates have back-up and back-up-back-up opportunities. By making impersonal and non-committal applications, you appear desperate. A focused and careful effort suggests that you are not looking for any job - even if that may be the case.

I suggest the following template to help flesh out an honest and engaging first contact. The letter need not be a lengthy tome but a succinct summary that entices the reader to communicate with you further.


Introduce yourself.

How did you find out about the team? What interests you about it? What do you think of their market? Have you used their product or service? What did you think? Does the culture look great? What about it resonates with you?

What have you been up to? Who are you? What sort of things do you enjoy? What kind of person are you? What makes you laugh? What do you love? Any wild experiences? Show yourself. Open up. Let your geek flag fly. Have fun with it.

How can the company benefit from your skills? What makes you a worthwhile investment? Do you have any relatable accomplishments that can tantalize us?

Now, here is the magic: Before you submit a formal application, ask if you can have a casual chat with someone about the company. Music!

A sincere farewell and how you can be reached.


The secret ingredient in this template lies within the request for further communication. Almost without exception, the sharpest individuals I have discovered were the ones that first wanted to chat to see if the team felt right for them. Set your intention on meeting a human-being, asking about the work environment, and building a relationship. These relationships, when honest, are fruitful. Relax and be yourself.

You stand-out by realizing that a living, breathing, conscious person will receive your first contact.

Know Thyself

Looking through job listings is a harrowing experience. I empathize. It feels uncomfortable. Modern tech companies seek myriad, sometimes esoteric skill. The tasks are often broad-spectrum and it is rarely apparent what skills a team will need as it grows and pivots. Even if you are an efficient worker with a sturdy back-bone of relevant experience, bulbous role demands and narrow definitions can make you feel awkward and out of place.

Looking at yourself as a peg and the role as a hole is asking for disharmonious existence. You risk hedging some of your strongest traits, while inflating some of your lesser-formed abilities. After bending to make it fit, even if you wind up getting the role, it should come as no surprise when it does not make you feel fulfilled. To avoid this trap, put your best foot forward.

Enjoy some introspection and contemplate what you are best at. Ask yourself challenging questions about what you feel you enjoy and the sort of work you see yourself doing:

"Do I really like programming, or do I like sitting on the computer?"

"I do not think I would make a good project manager, but I do love people..."

"Perhaps I write better than I code?"

"I think JavaScript might give me hives."

Be honest with yourself and see what your greatest skills and traits are. Do not try to stretch ‘intermediate JavaScript’ programmer because you finished a textbook, or ’SysAdmin’ because you got Counter-Strike running on Linux once. If you are unsure about what you are good at, ask your loved ones. Everyone is different; own your positive traits and present them with your strong-foot forward.

Instead of applying yourself to a companies' roles, apply to a company as yourself. Often times companies will not only allow, but reward, individuals who apply outside of any specific role. This is not to say that you should develop an attitude where you only work on what you would like to. In contrast, you can show that you are uniquely suited to tackle a variety of tasks, using your mightiest skills.

Look for the companies that speak to your heart. Do you like their culture? Are you a fan of their product? Perhaps they do not have anything for you right now, but there is no harm in reaching out with a personal touch to build a relationship. When your best version of you finds a role and team that just fits, work will not feel like work.


Before embarking on your journey, understand that finding your first remote opportunity is challenging. If you are a junior, it will be more difficult. Do not compensate for a lack of experience by lying or artificially inflating your importance or your abilities. Be honest with yourself and your abilities. The road to remote work is paved with genuine relationships, perseverance and hard-work. You will get there.

Good luck!

PS. Feel free to Tweet at me if you would like some advice.