Every 10–15 years, a major shift comes along.

It doesn’t just change the tools we use.

It changes the rules of the game.

This is true across work, industries, and careers.

And it’s true for HOW we do work, become experts, and build our careers.

Think back. We moved from:

• Mailed resumes to online applications

• Classifieds to Monster.com to LinkedIn

• From job fairs to remote interviews

Each shift created new winners and losers as some candidates adjusted to this new normal, while others were left behind, wondering why they weren’t getting calls for interviews.

We’re at the start of another shift.

And we’re underestimating how AI will change how we search for new roles.

Here’s what you’ll learn today:

• 🔎 How you can use AI to find your next role – even before it’s posted

• 📊 Why sending out hundreds of applications isn’t the answer anymore

• 🛠️ The exact tools I’d use to stand out from other candidates

Let’s get into it.

⚡ Claim Your Unfair Advantage

Most people are just using ChatGPT to help write their resume and clean up their cover letter.

This is barely scratching the surface.

Here’s how AI could transform the job search process:

• Spot company signals to predict job openings up to 2-3 weeks before posting

• Smart automation can personalize and send 50+ tailored outreach messages a day

• AI-powered workflows can compress a 15-hour job search process into just 45 minutes

Now, allow me to share something personal with you:

I’m not a crier.

I didn’t cry when my first child was born. Or when I saw my wife walking down the aisle. (A fact that she reminds me of at least once a year.)

But I’m so excited about this, I’m nearly in tears.

Because when it comes to productivity + automation + helping people land jobs faster… cue the water works, my friends.

And like every platform shift before it, the unfair advantage goes to the people who adapt early.

Use it fast—and execute well—and you’ll stop applying with the masses and start having real conversations with decision makers.

To show this isn’t just hype, I want to get into the weeds with you and show exactly how I’d use this AI-powered system myself to land my next role.

🛠️ A New Framework for an AI Job Search System

The traditional job search looks something like this:

1. Spend hours scrolling through job boards

2. Apply to dozens of positions with slight resume tweaks

3. Hope someone notices you in the sea of applications

4. Repeat until you’re so exhausted you opt out of the game

This is an actual email from a friend of a friend. I don’t want this for you.

This approach is outdated.

Like my girl Taylor would say,

“I think I’ve seen this film before, and I didn’t like the ending.”

With AI-powered tools, we can transform this experience:

1. 🔍 Smart Discovery: Find opportunities before they’re widely known

2. ✅ Targeted Optimization: Tailor your materials with precision

3. 🚀 Efficient Application: Apply to more jobs in less time

4. 🤝 Strategic Networking: Connect with the right people

5. 🎯 Impactful Interviewing: Prepare like never before

Let’s break down each step with specific tools and tactics.

🔍 Step 1: Smart Job Discovery

The Traditional Way: Endlessly scroll through LinkedIn, Google, and other job boards, manually filtering through hundreds of listings. Use alerts. Edit the LinkedIn URL so you see a job opening the minute it’s posted and START. APPLYING. FAST!

The AI Way: Let your AI systems both track job openings and early signals for hiring (e.g. funding announcements, geographic expansion, leadership changes and more) to discover roles before they’re widely posted.

🧰 Recommended tools:

Clay – An AI-powered research and outreach platform that can monitor companies for new roles.

👉 Do this in Clay:

• Sign up for Clay free trial

• Click Add Source

• Use filters to select role, industry, employment type, and keywords (e.g. “remote”)

• Set a schedule for running the source, e.g. every 6 hours

• Add an Export to a Google Sheet column

• Get your target open roles piped to your Google sheet every 6 hours

⚒️ Bonus: More tools to consider:

Perplexity – AI-powered search engine that can uncover job opportunities from diverse sources.

Visualping – Monitor company career pages for changes and be first to know when new roles open.

✅ Step 2: Targeted Resume Optimization

The Traditional Way: Manually adjust your resume for each application, guessing which keywords might matter.

The AI Way: Use AI to analyze job descriptions and your experience, then optimize your resume for maximum relevance and impact.

🧰 Recommended tools:

Teal – Helps you optimize your resume, track applications, and provides side-by-side comparisons between your resume and job descriptions.

👉 Do this in Teal:

1. Upload your resume to Teal

2. Add the job description you’re targeting

3. Review the match score

4. Implement AI-suggested improvements to better align your experience with the role

These are the exact steps I used to improve my ATS match scores by 180% in about 30 minutes, after I optimized my resume for a human reader.

⚒️ Bonus: More tools to consider:

Claude – I prefer Claude over ChatGPT for working on my marketing materials (e.g. resume, cover letter, and LinkedIn profile) as I find it writes it a more natural language ChatGPT.

🚀 Step 3: Efficient Application

The Traditional Way: Manually fill out the same information across dozens of different application systems, wasting hours on repetitive data entry.

The AI Way: Automate the application process while maintaining personalization, allowing you to apply to more relevant roles in less time.

Tools That Transform This Step:

🧰 Recommended tools:

Simplify – Browser extension that autofills job applications across platforms.

👉 Do this in Simplify:

1. Install the Simplify browser extension

2. When you find a job you want to apply for, click the Simplify icon

3. Review the autofilled application details

4. Add personalized elements before submitting

While Simplify is helpful, I want to be realistic about what it can do. The tool saves time with auto-filling applications, but it doesn’t work on every job site. When it does, you’re only shaving minutes per application.

But in today’s competitive job market where quantity and quality matter, saving even a few minutes per application adds up to valuable time saved over your job search.

⚒️ Bonus: More tools to consider:

Text expanders – My preference is atext. A text expander allows you to use shortkeys to “expand” your text. Another time saving optimization that shaves minutes off of applications (plus many other workflows).

⚡ Hey, so I’m going to test a new program where I cover this system, step-by-step, in crazy detail… so you can land your next remote role faster, with AI.

Here’s what you’ll learn:

• ✅ Find real remote jobs faster using AI—no more endless scrolling

• 🧠 How to write resumes and cover letters for people AND the ATS

• 🎯 Reach the right people directly (even if you don’t have a big network)

• 📬 Send better outreach messages with smart tools that do the heavy lifting

• 🚀 Build a simple job search system so you don’t waste time or burn out

I’m creating an early access list that includes special pricing for everyone on it 😎

Qq:

INSERT 2025.05.13 POLL EARLY ACCESS LIST

Okay, let’s cover the last two steps:

🤝 Step 4: Strategic Networking

The Traditional Way: Randomly connect with people at target companies, sending generic “Can I pick your brain?” messages.

The AI Way: Identify the exact right people to connect with, understand their backgrounds and interests, and craft personalized outreach that resonates.

🧰 Recommended tools:

Clay – An AI-powered research and outreach platform that can help with research and outreach to people at scale

👉 Do this in Clay:

• Sign up for Clay free trial

• Import your outreach list into Clay

• Enrich their profiles with data from LinkedIn, Twitter, or even company bios

• Use AI (e.g. ChatGPT, Gemini, Claude, whatever LLM you want to use, all inside Clay) to summarize your relationship, recent posts, and shared interests

• Generate messages that still sound human, but take seconds to create

• Send through an integration in Clay or export to a Google sheet

You gain a lot of speed with this approach, but because you’re relying more on AI, double-check the outputs to make sure you haven’t gone off the rails.

⚒️ Bonus: More tools to consider:

Happenstance – This tool compiles LinkedIn and Gmail Contacts so you can use AI to surface people you may already know inside target companies. I’m still playing around with this and will report back if I find particularly good use cases.

🎯 Step 5: Impactful Interviewing

The Traditional Way: Practice general interview questions and hope they cover what you’ll be asked.

The AI Way: Use AI to simulate company-specific interviews, get feedback on your responses, and prepare for exactly what you’ll face.

🧰 Recommended tools:

Poised – AI-powered interview coach that provides real-time feedback during interviews

👉 What feedback you get with Poised:

• Non-distracting, real-time feedback while speaking

• Feedback on conciseness, hedging words, filler words, etc.

• Immediate and actionable feedback

⚒️ Bonus: More tools to consider:

Google NotebookLM – My client, Eric, trained a NotebookLM with his interview answers and found listening to it helped prep for interviews (it worked; he landed an internal promotion in 3 months).

💫 The Bottom Line

The AI revolution in job searching isn’t just coming. It’s here. If you can embrace these tools now, you’re going to have an advantage in a competitive market.

Keep a few things in mind:

1. Tool costs add up – Many of these tools have free tiers, but the most powerful features often require paid subscriptions.

2. AI isn’t perfect – Always review AI-generated content for accuracy and tone before using it.

3. Be human – No AI can replace authentic relationships and your unique personality.

Now, here’s your action plan:

1. Start small – Pick just ONE of these tools to implement this week

2. Learn the platform – Invest time in understanding how to leverage it effectively

3. Measure results – Track improvements in your application-to-interview ratio

4. Expand gradually – Add new tools as you master each one

Remember: This isn’t about applying to more jobs. It’s about applying smarter to the right jobs.

Which of these tools are you most excited to try? Hit reply and let me know!

Talk soon 👋