📝 The Complete Resume Rewrite Guide Using AI

Hello there 😎 

Tomorrow we close on a house 🏡 

…and then I’ll pull my kids out of summer camp for our family holiday in the Poconos.

It’s a busy week.

But man, I was pumped to sit down and get this newsletter out.

I’ve packed it with tactics that will help you land more interviews.

See, I've been quietly running my Land The Interview service for the past few weeks, helping people overhaul their resumes and LinkedIn profiles.

It's been incredibly rewarding, and I'm learning a ton about what's actually stopping people from getting interviews, especially as “referral theater” becomes more of a thing.

Note: I’m opening more spots in the next few weeks. Click below to join the waitlist.

Here's what I keep seeing:

Smart, qualified people making the same five mistakes that kill their chances before a human ever sees their resume.

The good news? Every single one of these problems can be fixed with the right AI approach.

Here's what you'll learn today:

• The 5 most common resume mistakes that prevent interviews

• How to use AI to fix each problem (with specific prompts)

• Why keyword stuffing is backfiring and what to do instead

• The right sequence for optimizing your resume with AI tools

...and more!

But first, let's look at some open roles I'm excited about.

🚨 The 5 Resume Mistakes Killing Your Interview Chances

After reviewing dozens of resumes, here are the problems I see most often (and how AI can fix them):

❌ Mistake 1: Treating Your Target Role Like an Afterthought

This is the biggest one.

Here's what it looks like: someone applies for Product Manager roles, but their resume says "Product Owner," "Business Analyst," and "Project Coordinator" across different jobs.

The problem: The ATS is looking for title matches. So are hiring managers. They’ll scan a resume in 6 seconds. If they don't immediately see the exact title they're hiring for, you're out.

👉 Do this:

This one is pretty straightforward, but if you're looking for an AI solution, here's how I would do it.

✍️ Use Claude to analyze your experience and align it with your target role:

Example transformation:

• Before: "Business Analyst II"

• After: "Product Manager" (if you were doing PM work)

Remember: titles are made up anyway. Chief Happiness Officer? Customer Support Rockstar? People literally make stuff up on LinkedIn. Focus on:

• Giving them what they’re looking for

• …while still honestly and accurately representing what you actually did

BTW, here’s a way you can (honestly and ethically) bypass the ATS completely.

❌ Mistake 2: Keyword Stuffing Without Strategy

“Dude,” I asked, “What’s up with this skills section?”

My client responded:

The result? A skills section that looked like this:

Core Competencies: Product Strategy | Team Building | Experimentation | Talent Development | Data & Analytics | User Empathy | Metrics & OKRs | Cross-functional Leadership | Process Improvement | Growth

The problem: This approach puts keywords first, story second. You end up with a random inventory of skills that tells no narrative.

Here's a one-two punch that's actually getting my clients multiple recruiter messages:

🔍 Step 1: Use Teal as a “resume reality check”

Start here to get your baseline. Upload your current resume plus a target job description to Teal.

Teal shows you exactly why you're not getting interviews. It gives you an ATS compatibility score and highlights the specific keywords you're missing.

👉 Do this:

Here’s a more detailed guide on using Teal for this exact purpose.

✍️ Step 2: Use Claude to wordsmith the resume

Don't ask for a generic rewrite. Be specific about what Teal found:

Right now, Claude is better than ChatGPT for this. More natural, less likely to sound robotic, and better at incorporating keywords without disrupting your narrative.

Why this combo works:

• Teal tells you WHAT to fix (specific missing keywords)

• Claude tells you HOW to fix it (natural integration)

Never sacrifice storytelling for keyword density!

The goal is strategic optimization, not keyword stuffing. Your resume should still sound human while hitting the ATS requirements.

Better approach:

1. Use Teal to identify your biggest keyword gaps

2. Use Claude to naturally incorporate missing terms

3. Re-upload to Teal to check your improved score

4. Repeat until you hit 60%+ match on target roles

❌ Mistake 3: Writing Job Descriptions Instead of Impact Statements

Most resumes read like this: "Managed social media accounts and collaborated with cross-functional teams to support marketing initiatives."

That's a job description, not an achievement.

👉 Do this:

Example transformation:

• Before: "Managed social media accounts for [company]."

• After: "Increased social media engagement by 150% and generated 200+ qualified leads monthly by implementing data-driven content strategy across Instagram and LinkedIn."

I used to coach people on how to find the metrics and then how to weave it into the story.

To be honest, it’s hard to teach. 😅

This was always the most time-intensive part of helping clients with their resumes. But now it makes it so much easier once you've got the metric you want to incorporate.

✍️ Use Claude to transform responsibilities into impact statements:

📢 Enjoying Remote LifeOS?

If you are, consider sharing this with a friend who could use help landing their next role.

As a thank you, I’ll send you my Ultimate Guide to AI Tools for Job Searching.

I spent 20 hours testing, iterating, refining, and editing this guide You’re gonna dig it.

Just use your referral code below 👇

❌ Mistake 4: Making Yourself the Hero

Here's a mindset shift that changes everything:

You are not the hero of your resume.

Most resumes have "main character energy" and focus on what the candidate wants. But hiring managers care about what you can do for them.

👉 Do this (no AI required):

Example transformation:

• Before: "Seeking a challenging Product Manager role where I can grow my skills and advance my career."

• After: "Product Manager who increases user activation rates by 40%+ through data-driven experimentation and cross-functional collaboration."

You can also use AI to help you with this if you’re struggling to self-diagnose:

✍️ Use Claude to flip your perspective:

❌ Mistake 5: Throwing the Kitchen Sink At It Instead of Curating

Your resume is not a detailed chronology of your work history.

It's a curated story that supports your target narrative.

I see people including every job they've ever had, even when it hurts their story.

✍️ Use Claude to audit what fits:

👉 Do this:

Create a "master resume" with everything.

Then create targeted versions that only include experiences that support your specific narrative.

For each version of your resume, read it from the bottom to the top and ask yourself:

Example: If you're applying for product roles, your internship at a newspaper doesn't belong (unless you're early in your career).

Focus on experiences that demonstrate relevant skills.

🔧 The Right AI Workflow for Resume Optimization

Told you we’d pack in a lot. To recap, here's the sequence that actually works:

Step 1: Write Your Story First. Use Claude to help structure your narrative, but don't worry about keywords yet.

Step 2: Perfect Your Impact Statements. Transform responsibilities into achievements using the AI prompts above.

Step 3: Optimize for Keywords. Use Teal to compare your finalized resume against job descriptions and identify strategic keyword opportunities.

Step 4: Test and Iterate. Use different versions for different types of roles, tracking which gets better response rates.

And some quick tips that apply to everyone:

• Don't let AI write your whole resume. Use it to improve structure, clarity, and impact, but your personality and voice should shine through.

• Test your resume with real people. Ask someone in your target field: "Based on this resume, would you interview this person for [role]?"

• Keep it simple. No tables, columns, or fancy formatting. ATS systems hate complexity. Simple beats clever every time.

• Focus on the experience section. It's the main course. Everything else is garnish. Put 80% of your effort here.

💫 The Bottom Line

Your resume's job is simple: convince someone you're worth 30 minutes of their time.

Most resumes fail because they try to be everything to everyone, stuff in random keywords, or focus on what the candidate wants instead of what the company needs.

AI can fix all of these problems, but only if you use it as a strategic writing partner that helps you tell a more compelling story.

Remember:

• Clear beats clever

• Story beats chronology

• Impact beats responsibilities

Let me know how it goes!

I love meeting new people. Say hi on LinkedIn 👋

🤝 When you’re ready, here are 2 ways I can help you with remote work:

That’s a wrap. See you next week 👋