My first remote job
5 min read

My first remote job

Today I'm telling you the full back story of how I landed my first remote job. It was a few months of hard work and fast iteration. But I got a high paying remote job for a US startup.


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

Last week I shared with you my learnings from working as a remote contractor for past 7 years. First it was a daunting new world, but as it settled in I actually learned some great upsides of that arrangement.

Today I'm getting a bit personal. I'm telling you the full back story of how I landed my first remote job. It was a few months of hard work and fast iteration. But I got a high paying remote job for a US startup.

This was in 2016, and the highest salary I had ever earned until then was around $25k/year, working in the office for a local company. I was really shooting for the stars here by trying a remote job paying several times more. As you can imagine, this hard work paid off, as I landed a life changing remote job.

Let me tell you the full story, step by step, so you can copy and adapt to your own situation:

1) Finding what role to target

It's important to focus, but it's even more important to learn what's the right thing to focus on. I didn't know, so I asked myself all these questions:

• What skills do I have?

• What do I have experience doing?

• What story can I tell about my past work?

• What companies will that story resonate with?

• What technical tests can I actually succeed at?

My prior experience, back in 2016, was:

• 3 years as a Software Engineer

• 3 years as a Startup CTO

And my first goal was to identify open roles which:

• I would be a strong enough candidate to get them

• I could work remote from my home country

• Paid he highest possible salary ($100k/year was the goal)

2) Applying to hundreds of roles

I didn't have a clear clue what to aim for, but I had the most important thing a person can have: I had the energy to chase my dream!

So, I applied to a very broad range of roles:

• Different titles

• Different seniorities

• Different company sizes

• Different locations (few job boards had "remote" as an option back then)

For job titles, I went for things like:

• Software Engineer

• Software Architect

• Engineering Manager

• Product Manager

• VP of Engineering


For companies, I preferred startups from Seed to Series B, but also tested larger companies.

For locations, I filtered startups paying $100k+ and applied. Surprisingly, many were open to interview me, even if was only open to working remotely.

I covered the field with more than 100 applications in the first few days. Then, I went from there and iterated with the learnings.

3) Learning from feedback

Goes without saying. But this is the usual breakdown:

• 80%+ of companies don't ever reply.

• 10% or so reject in written format.

It's important to NOT get discouraged by these rejections. Rejection is part of life, and landing a high paying remote job is a tight funnel. But I only needed one such offer, just one.

So I kept looking for it. From these rejections, I learned that either I shouldn't apply to such companies/roles or that I should position myself differently!

The remaining 5-10% of applications is where the fun begins. I was invited to interviews and code tests, but beyond that. I learned what worked.

For me, I had higher traction in applications for Startup CTO roles. Specifically from startups located in highest cost places (SF, NY, Boston, etc).

I doubled down on those roles. Before, I was simply applying to job openings, but after learning what roles I should focus on, I started:

• Searching on Linkedin for startups without a CTO

• Asking for intros to such companies

• Reaching out cold to such Founders

It landed me around 15-20 interviews.

4) Learning from interviews

I learned that I had a reasonably high conversion from interview to offer, but one thing surprised me: Some companies weren't VC funded (yet?), and the offer was contingent on closing some upcoming round. It meant they didn't have the money to hire me as their CTO immediately, and it was very frustrating!

From that point onwards I opened every new interview with the question "What's your runway and funding situation?". Some interviews would take only 10 minutes, when the company wasn't actually ready to make the hire I moved on.

I also focused my cold application process even further:

• Set Google alerts for Seed and Series A funding on US based startups

• Look up Crunchbase before interviews (that info was open back then)

I started rejecting interviews with startups that weren't funded, and taking the time to research and prepare for those that were funded and ready to hire.

5) Optimising for the highest possible offer

As soon as it became clear to me that I could get offers, I wanted to have several on the table at the same time.

Only that way I could:

• Chose the one I liked the most

• Make sure it was fully remote

• Negotiate the salary up (by making them compete against each other)

To achieve these goals I did two simple things:

• Booked last interviews around the same time when possible. This means accelerating some processes and gently delaying others.

• Told every interviewer that I have other offers on the table and needed to decide by X date (in 2 weeks).

6) Choosing the "best" offer

I got a total of 7 offers on the table.

• 4 offers I dismissed immediately because either the salary was below $100k or the roles weren't fully remote.

• 3 offers were "on target": Fully remote and paid above $100k/year. All from well funded US-based startups.

From those remote offers paying upwards of $100k, I accepted the one where I most liked the company, the Founder, the mission and the challenge. Curiously it wasn't the highest paid offer. Accepting a new job is a complex step, and it's way beyond the salary.

For me, getting this job was truly life changing. I increased my salary 500% while keeping the same cost of living. Salary Arbitrage is a powerful thing!

Since then, I've helped some people around me find remote jobs. Now, I'm telling you all on this newsletter too.

My key takeaways from my own job search were:

• Find what's *your* target company and role

• Apply like crazy!!

• Embrace rejection, learn from it and iterate

• Prepare for interviews and tests

And above all:

• Be patient! This whole process took me 4 months.

In case you're actively looking for a remote job, you might want to have a look at this list of 1000+ companies hiring remote roles right now. I built this free resource just about 2 months ago, and since then 15000 have visited the page and applied to remote roles listed there. Have a look!

I'm also launching soon my first ever cohort based course and private community, where I'll be breaking down my knowledge into modules, and will help a batch of remote job seekers find a remote job. The launch will be private, join the waitlist and stay tuned.

Thanks for reading this newsletter until the end. You can read all past editions here. Make sure to share the link 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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