Hey {{ first_name | portfolio pather }},

We’ve featured many amazing people over the years, but today we have our first-ever guest post from fellow portfolio pather, Chris Ming.

Let’s dive right in.

Today, in 10 minutes or less, you’ll learn:

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The first 6 years of my tech career were spent in SF offices.

While I feel grateful for building in-person relationships in my 20’s, it wasn’t until I moved to Singapore and COVID lockdowns hit shortly after, that I realized the power of remote work.

I built a remote product team that spanned Singapore, US, Indonesia, Philippines, and Vietnam. I discovered how much leverage I could get on my time not needing to commute 1-2 hours (let alone fly across countries).

Fast forward to 2 years ago, I connected with Chris Ming through Linkedin DMs.

We quickly bonded over expat life (he lived in Dublin then).

Since then, I’ve gotten to know him through our recurring masterminds.

In particular, I have been impressed with how he’s built his remote career—navigating the same transitions that many professionals in our community are currently pursuing. And now, his insights have also helped many professionals accelerate their remote job transitions.

Without further ado, enter Chris:

Chris Ming is the founder of RemoteLifeOS, where he teaches people how to land remote jobs using his 6-step strategy & the latest AI tools. His experience at Clay, Persefoni, Reforge, Noom, and I Will Teach has shaped his remote job search strategy, which he's tested while living in Europe and across the US. He lives with his family in Philadelphia. You can connect with him on Linkedin.

My biggest fear? Waking up to realize I traded my best years—the years my kids needed me most—for a promotion.

That's the Old Career Deal: Climb the ladder, get promoted, and (fingers crossed!) someday you gain more freedom.

But there's a New Career Deal: Build flexibility on your own terms—through remote work and multiple income streams.

In my experience, remote work makes a portfolio career possible.

It gives you time back, which turns into leverage to create your own portfolio path 🙂

As someone who's been working remotely for 10+ years and coaching dozens of successful remote job transitions (many going from zero interviews to multiple offers), I've also seen what works and what doesn't.

So find your favorite Taylor Swift album on Spotify (mine's "Reputation"), put it on in the background, and let's dive in!

Companies are pulling back remote offerings, with LinkedIn reporting a 57% drop in fully remote job postings from their peak.

Yet, these dwindling opportunities still attract over half of all job applications.

So is pursuing remote work even worth it anymore?

Absolutely. But the old “spray-and-pray” approach no longer works.

You need a better strategy that acknowledges the new reality of remote work in 2025.

One of my clients came to me after months of sending applications into the void. She'd been doing everything "by the book" but getting zero responses.

After implementing the system below, she landed four interviews within four weeks and a job offer within another few weeks.

Here are 6 strategies I recommend to earn the freedom to work remotely (and how to supercharge your search with AI):

The best roles are rarely listed. You have to start with companies you believe in, not just job boards.

👉 Do this: Use a tool like Perplexity to find companies by industry and stage.

✍️ Use this prompt:

Once you have your list, start researching each one (more on that below).

Save the ones that align with your values, product interests, or mission.

Research is the secret sauce.

This applies to every stage in your job search funnel, but it starts with company research.

👉 Do this: Use Perplexity or Manus to get smart, structured intel on a company's priorities.

✍️ Use this prompt:

Look for:

In my first week of Brazilian Jiu-Jitsu, my coach drilled this into my head:

Position before submission.

The same is true in your job search:

No submissions until you’ve positioned yourself as an ideal candidate. And that starts with the deep research.

Titles are fungible.

This means they change, from company to company (and even within the same company, over time!)

So make sure you’re using the right titles in your resume, LinkedIn profile, and cover letter, depending on the company that you're targeting.

👉 Do this: Use LinkedIn People Search + ChatGPT to understand naming conventions.

Example:

When I worked at Reforge, I was a “Product Manager." At Noom, I was a "Senior Product Manager, Growth." At Persefoni, I was a "Principle Growth PM."

Same role, different titles 🤷

Also, as a general rule, stay away from cutesy, quirky titles that sound clever, but no one uses:

Your marketing materials (your resume, LinkedIn profile, and cover letter) need to work together as a tightly woven system to get you noticed in a competitive remote job market.

This guide breaks down how to make every part of your application stand out.

And it all trickles down from you resume, so getting that right is more crucial than ever.

Fortunately, there are tools that make this easy.

Teal is an AI-powered platform that analyzes how well your resume matches specific job descriptions. Most companies use Applicant Tracking Systems (ATS) that filter resumes based on keyword matching before a human ever sees them.

👉 Do this: Upload your resume and a job description to Teal (it’s free) The tool will:

Once you’re scoring above a 50% Match Score, start copying the content from your resume and pasting it into your LinkedIn profile.

My client, DK, is a product designer. He followed these steps, and within 10 days, he had 3 recruiters reach out and schedule screens.

I asked him when was the last time he had a recruiter reach out to him on LinkedIn.

“Never,” he said. “This has NEVER happened to me before.”

Most job hunters waste hours manually scrolling LinkedIn.

There's a smarter way using AI tools to automate your search.

👉 Do this: Use Clay to automate your remote job discovery process.

Here's how to set it up:

This creates a personal job feed of only relevant opportunities, eliminating endless scrolling.

The full workflow looks like this:

This system saves my clients 5-10 hours per week of manual searching while surfacing higher quality opportunities.

Finding someone who already works at the company can make a huge difference. They can tell you what it's really like to work there, put in a good word for you, and sometimes even help your application get seen faster.

This isn't just about getting a referral. I’m talking about finding someone who's going to champion for you inside of the company.

How do you find that person?

You can manually go through all your LinkedIn contacts, or…

👉 Do this: You can try Happenstance.

This tool compiles LinkedIn and Gmail Contacts so you can use AI to surface people you may already know inside target companies.

Once you’ve found the person you want to reach out to:

✍️ Try this prompt in ChatGPT:

This message will be a decent first draft, but you’ll definitely want to massage it before you hit send.

Getting a remote job isn't just about working from home. It's about having more time to live your life the way you want to.

For example: when I moved to Ireland with my family and kept my US job, I saved 2 hours every day by not driving to work. I used this extra time to be with my kids, see Dublin, and work on small projects that grew into new ways to make money.

That's what makes remote work so great. You can use your free time to build other skills and create new opportunities for yourself.

The world of work is changing fast. The old playbook of sending out applications and hoping for the best doesn't work anymore, especially for competitive remote roles.

Instead, supercharge your approach with AI and:

Which of these steps will you implement first?

Thank you, Chris! For more tips or to connect with Chris directly, check out his Remote Life OS newsletter. You can also find Chris on Linkedin.