Remote work changed my life
4 min read

Remote work changed my life

I'll tell you how I landed my first high paying remote job, with step by step instructions that you can follow too. Hopefully, these will help you land a high paying remote job too!


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

The year was 2016, and I had just became a father for the first time. Money was tight, and I had been networking, applying and interviewing for remote roles in the US and UK for a few months.

I finally got 3 offers above $100k/year on the table, all from US startups. When the first salary came in after a few weeks, my wife couldn't believe it. The 5x salary bump was truly life changing for me and for my family.

Today I'll tell you how it happened, with step by step instructions that you can follow too. Hopefully, these will help you land a high paying remote job too!

Check out the 6 steps I followed to get the job:

1) Find the right role to target

For all the good things in life we need to focus before putting in the hard work. I asked some key questions to myself:

• 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?

• What am I optimising for in this job search?

My prior experience, back in 2016, was:

• 3 years as a Software Engineer

• 3 years as a Startup CTO

My goal was to land a job that would get me:

• Working from home

• The highest possible salary ($100k/year was a dream)

2) Apply to hundreds of opportunities

When I started applying, it was a new world for me, I had little idea what to shoot for. 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)

I applied to more than 300 jobs to see which combo I had the most success with. It's a numbers game after all.

For job titles, I went for things like:

• Software Engineer

• Engineering Manager

• Product Manager

• VP of Engineering


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

For locations, I filtered startups paying $100k+ and applied regardless of where they were based (most were in the US, though). Surprisingly, some were open to interview me, even if was only open to working remotely.

3) Learn from feedback and iterate

Goes without saying, but recruitment is a numbers game. High paying remote jobs are highly competitive, and that's creates a tight funnel. This is the usual breakdown:

• 80%+ of companies don't ever reply.

• 10% or so reject in written format.

From these, I learned that either I shouldn't apply to such companies/roles or that I should position differently!

The remaining 5-10% is where the fun begins!

I was invited to interviews and code tests, but beyond that. I learned what worked. I started seeing myself in interviews with similar companies, that demanded for a similar profile (mine!).

For me, I had higher traction in applications for Startup CTO roles. Specifically from startups located in places  where local salaries are very high (SF, NY, Boston, etc).

I doubled down on those roles.

Before, I was simply applying to job openings in job boards I learned to be the best for remote roles, but after learning where to focus 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 several interviews.

4) Learn from interviews

I learned that I had a reasonably high conversion from interview to offer, but then I hit an unforeseen setback: Some companies didn't have the money to pay the salary they had mentioned in the job description. These were early stage startups without enough revenues or funding, and the offer was contingent on closing some upcoming fundraising round. This was very frustrating!

From that point onwards I opened every new interview with the question "What's your runway and funding situation?". Some interviews started taking only 10 minutes, when the company wasn't actually ready to pay the salary I dropped from the process.

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.

5) Optimise 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. By having competition for me, I would be in a better position to:

• Chose the company I liked the most

• Make sure it was fully remote

• Negotiate the salary up

To achieve that I did two simple things:

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

• Tell every interviewer that I have other offers on the table and need to decide by X date (eg: in 2 weeks).

6) Choose the "best" offer

I got a total of 7 offers on the table.

• 4 offers I dismissed immediately because either salary was below $100k or 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 I got. Accepting a new job is a complex step with multiple variables. It's way beyond the salary.

Sergio, telling you this story made me live through it all again. I was very happy when I signed that contract and flew to San Francisco for onboarding. It felt like a dream, back then. Looking back, it was an inflection point in my career and in my life.

I wish I could inspire you to take the same steps, and find your own life changing remote job. Please make sure to reply to this email, or DM me on Twitter when you get it. I love receiving those happy news!!

One thing I didn't have back then, so I built it recently: A list of 1000+ companies actively hiring remote roles. I recommend applying directly (vs job boards), and reaching out to the Founders or Hiring Managers on Linkedin. Be early, be personal and be consistent. It will get you a long way. Good luck!

Thank you for reading this newsletter issue until the end, I loved writing it!

You can read all past editions of this newsletter 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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