I recently ran a live training on how to land your next remote job.

It was great. Lots of great questions, and I got a handful of messages afterwards from folks saying the tactics were helpful, and they were more hopeful about their job search again.

That meant a lot. Live trainings are something I want to keep doing more of this year.

So here’s one of the questions that came up in the session:

“Any advice of how I should AI to beat the HR AI systems?”

At first, I almost ignored it.

I thought it was kind of a gimmicky question. Like one of those “hack the ATS” YouTube videos.

But I’m glad I didn’t.

First, let’s look at some open roles I’m excited about.

🤖 How AI is Transforming Job Search

I asked for details. Here’s what he said:

“I assume recruiters are using AI. How else can they analyze 1000–3000 applications for one job? So I want to know how to tailor my resume and cover letter so their AI systems flag me as a high match.”

This is a fair question.

AI is changing how we work—and it’s already changing how we hire.

Brian Balfour said it well in AI Native Product Teams

“A technological shift comes along that doesn’t just change how we build products—it rewrites the entire playbook.”

He continues later:

“The shift to cloud the enabled subscription to become the dominant monetization model. This enabled lower barriers to entry, free trial models, and different dimensions of charging for features and usage.”

This shift is reshaping how we write, research, and communicate at work.

If that’s true (I agree it is), then it’s only logical that AI will change how we find work, too.

⚡ The Revolution Is Already Here

In fact, it already has.

Without realizing it, AI has quietly become one of the most powerful tools in my own job search workflow.

Here’s what it’s helped me do:

For example, I always said that company and role research is the secret sauce to standing out in your application and interview.

But it was a pain.

Using AI, I can now teach clients how to complete their research in 10 minutes instead of hours.

It’s also changed how I write my cover letters. What used to take 30 minutes of manual personalization now takes just 3 minutes to complete.

These aren’t minor improvements.

For me and my clients, these are “I’m not sure how I lived without this” type of improvements.

And we’ve barely scratched the surface.

🐇 I’m Going Deeper (And Bringing You With Me)

So I started wondering…

What else could AI help with?

What if I used my own job search as a testing ground—an “AI guinea pig”—to try out the best tools across every stage of the remote job hunt?

For example, here are a few areas we could learn more about next:

🧭 Smarter job discovery to match faster & better with tools like:

• Simplify – A Chrome extension that auto-fills and recommends roles based on your preferences

• Massive – For more automated job discovery and tracking

• JobCopilot – For better filters and role matching

✍️ Better resumes, LinkedIn profiles, and portfolios with tools like:

• Teal – To tailor resumes to match ATS systems

• ChatGPT + Claude – Quickly revise copy, tailor cover letters, and match the tone of the company

⚡ Outreach and networking (where most people fall off). Some tools that could help:

• Apollo.io – Originally built for sales, now a great tool to find emails and manage outbound

• Lavender.ai – Improves email tone and effectiveness

🎤 More efficient interview prep so you can finally stop guessing what to say, with tools like:

• Final Round AI – Mock interview practice with feedback

• Poised – Get live feedback on pacing, tone, and clarity during calls

• Google Interview Warmup – A fee tool for practicing basic questions

I’ll be testing more in the coming weeks—and reporting back with what’s worth your time (and what’s not).

💫 The Bottom Line

AI has changed how we work. It can change how we find work too. I’m going to start going down this rabbit hole and reporting back what I find.

If there’s a specific stage you’re struggling with—discovery, networking, outreach, interviews—reply and I’ll see if I can dig into it for you.