A little over a month ago, I quit my job. After almost two years working with a company in Santiago, Chile, I decided it was time to go. We reached an agreement where I would be working from home once I got back to Spain, however, after a month and a half I realized that I didn’t want to continue and decided to look for other opportunities. More than that, I wanted to get a remote job.

That’s when my search started. From the beginning I knew that, given what I was looking for (a remote job) I could not just send out thousands of resumes or fill out countless applications online. I actually had a really good experience working for my previous company and I did not want to quit my job to end up working for a company that didn’t motivate me.

The conditions that I set for myself were: 1) I wanted to keep working in business development or sales for a startup or a tech company, and 2) They need to have a remote team in place or at least be okay with me working remotely.

I started talking to friends, former clients… but it didn’t really take me anywhere. So I ended up using the same strategy that got me dozens of clients during my time at my previous company: I started sending cold emails.

For those who are not familiar with the term, cold emailing is just writing to someone who doesn’t know you and isn’t expecting an email from you. It’s definitely not anything innovative and I didn’t invent the wheel, but it is an old sales strategy that, if executed correctly, works perfectly.

One of the best things about contacting startup companies is that, since they are (usually) small teams, with an horizontal hierarchy, decisions (including hiring decisions) are made quicker. For example: at the same I time I quit my job, one of my colleagues who had actually been at the company almost as long as I had also quit her job. She went back to the corporate world where she came from. Her recruiting process took two months, with seven interviews in total. Mine took three weeks and only two interviews before they extended me an offer.

remote job
This was me at a remote location. But I was not working at the time.

How did I do it? Step by step

First, I went on AngelList jobs, selected “remote” and “sales”, and got a list of companies that were looking for sales positions which were (initially at least) open to hire people for a remote job. The first thing I did was put them on a list and take a very careful look at all their websites. I wanted to understand what their business was, what they do, what stage they were in, and what I would be doing for them.

After I made sure I liked what I saw, I put them on a google sheet to keep track of who I was writing to and when, as well as the responses I was receiving.

Second step: LinkedIn. Who’s the decision maker here? CEO, COOs, HR Managers… Every company is different and depending on their size you have more chances of getting a response if you email different people. Usually if the company is smaller than 30-40 employees, you can email the CEO directly. If it is bigger than 50, you can email the COO (Chief of Operations, they are usually above the HR Manager). If the company is bigger than 100, your best bet is the HR Manager. Although I always recommend emailing all of them, what’s there to lose?

Guessing someone’s work email address usually isn’t too hard (name@company.com or name.lastname@company.com) although there are exceptions. Once I figured out the type of company I wanted to work for and the right person to email, I crafted an email where I explained what I know about their company, why I wanted to work with them, and who I was. I would finish my emails with a call-to-action, asking them to talk over Skype or giving them my cellphone so they can reach me directly.

Applying for jobs (or looking for clients if you are a freelancer) is not easy and it requires time. It is almost a full-time job in itself. You will need to dedicate a fair amount of time for each job application that you send. You can’t pretend to send out a canned email to jobs@company.com without taking at least 5 minutes to read their website and expect a meaningful response. I actually would never send an email to a generic jobs@company.com email address. Those inboxes are always full of unread messages and the person in charge of reviewing them barely has time to go over all those resumes. However, if you send your application email directly to someone that is usually not in charge of reviewing resumes (such as a CEO) there are three possible outcomes:

1. They ignore you. But the intern in charge of reviewing resumes could have ignored you too. Nothing to lose.

2. They forward your email to the HR Manager. In that case, the HR Manager will probably spend more time reviewing your profile as this is a task that is coming from high up in the company.

3. The CEO likes you and schedules an interview with you.

The most important thing you should keep in mind is calling their attention. And no, calling someone’s attention is not about creating a colourful resume with tons of fonts, images, and icons unless you are applying for a creative/artistic/design job. Those resumes are usually hiding a lack of meaningful content. Calling someone’s attention is showing them you know your stuff:

– Show them that you understand their product, customer base, market fit.

– Propose to implement a sales/marketing/whatever your field is strategy that you have implemented (and been successful with) before. Keep in mind that this is something they could ask you during an interview. Avoid the BS.

– Read their case studies and try to find similarities to your profile or previous experience.

Once you have written about their company, your experience, your interest in working with them and why you think you could be a good fit, tell them more about you. But don’t copy-paste anything from your CV. Tell them which one of their job offers you are interested in and why, what your expertise is, and what you have been up to lately. A few lines is sufficient.

Lastly, refer them to some links or files where they can find more information about you. Attaching your CV is optional, as your LinkedIn profile should be enough. And don’t forget to propose to talk to them over Skype or the phone.

Although it’s true I mostly looked on AngelList, the majority of the companies on my list were startups that I liked, whether they were hiring or not. In some cases I had already used their software and others just appealed to me. These are actually the type of companies that you have more chances of getting an interview with. The fact that sometimes companies don’t have openings published does not mean they are not hiring. Contacting these companies is even better than ones with openings published, as they are probably not receiving a large volume of resumes and they can spend more time looking at yours. Plus, if you already know their product/service, you can tell them why you like them in your application email.

The most important thing to keep in mind is how you position yourself as a candidate: do not present yourself as someone who is just looking for a job, but as someone who can truly help them.

What to do next

Four days after sending out my first email I received an answer from a company. It wasn’t the only one, actually:


Interesting: There are several add-ons for gmail that allow you to see who opens your emails, when they do it, and even what device they use to open it. This is actually very useful. One example is Hubspot Sales, whose free version works perfectly (200 email notifications per month).

I was actually very lucky and did not have to look for too long. I only contacted 14 companies in total. Most of the people I contacted were CEOs and HR Managers, of which, 12 opened my emails, 6 took their time to email me back, and 4 of them said “sure, let’s meet”.

The best thing about looking for a remote job? There. Are. No. Borders. This is such a simple detail but it exponentially increases your probabilities of finding a job. What if you didn’t have to focus your search in just one city, region, or country? What if you could literally talk to tens of companies located all over the world? In my case, only 2 of the 4 companies I met over Skype were located in Europe.

What do we do when someone is not replying to your remote job application? Easy: email them again. We tend to see potential employers as some sort gods that you must not piss off. No. They are just people with very busy schedules. A silence, in this case, does not mean “no”. How many times did you forget to email/text someone back? Multiply the number of emails, calls, texts, and slack messages you receive in a normal day by 10. That’s a CEO’s average. It is normal that your email fell under the radar.

A quick email like this can work pretty well:

Hi [Name]

I am following up regarding my application for the (blank) position.

I would love to talk to you to get to know more about the position, as well as goals for the next few months regarding (blank) and see how I can help you achieve them.

How does your calendar look for a Skype call?


Now, before we send this follow up email, it’s important to see how interested our potential employer is. This is what we use Hubspot Sales for. For example, if our potential employer only opened the email once in the last, let’s say, seven days. That’s not a good sign. Now, stay on the lookout for any of these signs:

– They open your email several times, especially after work hours.

– They open your email from their computer, and later during the day, from their smartphone. This usually means that they are checking your email during their free time..

– They visited your LinkedIn profile and keep opening your email afterwards.

– They forward it to someone else on the team

A killer move is to always have a draft ready to send, and once you receive a notification saying that they have just opened your email, send it. They will be more likely to respond if they were already thinking about you.

How many times should you follow up? I honestly do not have an answer for that, and it really depends on how they react to your email. But I usually stop after two follow ups if I see that there’s really nothing to do.

Now, are you thinking about looking for a remote job? or just a regular job at a startup? If you need contacts, help with your CV, email templates, or just have no idea where to start, send me an email and let’s talk.

We will also be curating list of startups hiring for non-tech remote jobs like this one every month. If you want to stay up to date on companies hiring for non-tech remote jobs, you should consider joining our mailing list. Only 1 email per month and no spam, ever:

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