🔬 Can AI Help You Land a Job in 30 Days?

Plus: Open roles at OpenTable, Toast, Deel, Braze, Webflow, Cloudflare, UserTesting, Zoom, Workday, Sony, Zalando, Afterpay

Author

Chris Ming
October 07, 2025

Hello there 😎 

Last week I did something stupid 🙃 

I pitted four AI models against each other. Cage-match style. To see which one could actually help me land a job in 30 days.

Why? Because I’m always talking about using the right AI tool for your job search, but I wanted to know: soup to nuts, which tool would reign supreme?

So I tested:

  • ChatGPT5

  • Claude Sonnet 4.5

  • Manus Agent

  • Gemini 2.5 Flash

And scored them out of 10 (where 10 = this will absolutely land you a job and 0 = total garbage).

The results? Two clear winners. One bombed. And some good tactics that would actually work.

Here's what you'll learn today:

  • Which AI model gives the most actionable 30-day job search plan

  • The critical mistake 3 out of 4 models made (and why it kills your chances)

  • Specific tactics to steal from each model (including a copy-paste cold email template)

…and more!

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

💎 10+ High-Impact Remote Roles

🚨 Just added! These remote roles were hand-picked yesterday at 9:37 AM EST. Get your application in early to stand out from the crowd.

  • Principal PM at OpenTable 🇬🇧 Apply Here

  • Principal PM at Toast 🇺🇸 Apply Here

  • Principal PM, Treasury at Deel 🌎 Apply Here

  • Sr Technical PM at Braze 🇨🇦 Apply Here

  • Sr Manager, Product Design at Webflow 🇺🇸 Apply Here

  • Product Design Manager at Cloudflare 🇬🇧 Apply Here

  • PM at UserTesting 🇨🇦 Apply Here

  • Sr PM at Zoom Ireland Apply Here

  • Principal PM at Workday 🇨🇷 Apply Here

  • Manager, Marketing Operations at Sony Interactive Entertainment 🇺🇸 Apply Here

  • Principal PM, Marketing Automation at Zalando 🇩🇪 Apply Here

  • Sr Marketing Manager at Afterpay 🇺🇸 Apply Here

Keep reading for 20+ more opportunities 👇

👻 If you want to land 2x more interviews in 14 days, that's how I help. We:

  • Rebuild your resume to surface your value in under 6 seconds.

  • Restructure your LinkedIn profile so recruiters reach out to you.

  • Align your narrative around the role you actually want

Clients who do the work get 1-2 recruiter messages per week and 2x more interviews per 15 apps.

Like Josh, a product director:

❝

Chris helped me reframe my experience to make my resume and LinkedIn profile more engaging and focused. Now I’m in process with four different companies!

Josh C.

Or Mary, a general counsel:

❝

Chris gave me something I didn't even know I'd been looking for; a new perspective on my career that completely changed how I market myself but also how I think about who I am and what I bring to the table.

Mary M.

I have 3 spots opening next week.

Click “✅ Yes, please” below to get first access when spots open up.

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🥊 The Setup: One Prompt, Four AI Gladiators

I chose Product Manager as the test role because it's one of the most competitive remote positions with limited resources. If AI could crack this, it would work for other roles too.

I gave each AI model the exact same prompt:

Act as a career strategist and product coach. I want to land a Product Manager role within 30 days. Here are my constraints and context:

I have 2 years of Product Manager experience.My professional network is not very strong, so I cannot rely much on warm introductions.I can dedicate 4 hours per day to the job search.

Please design a step-by-step 30-day plan that maximizes my chances of landing interviews and offers. The plan should include: 1/ Weekly goals and milestones (e.g. positioning, outreach, interviews).

2/ A breakdown of daily tasks within my 4-hour limit.

3/ Concrete deliverables for each week (resume updates, outreach targets, interview practice, etc.).

4/ Tactics to compensate for my weak network (e.g. cold outreach, creating proof of work, leveraging communities).

5/ Pros and cons of each major tactic so I can prioritize effectively.

Some models asked follow-up questions. I answered them. Then I let each one cook 👨‍🍳

Let’s check out the results.

🏆 The Winners: ChatGPT Crushes It, Claude Close Behind

👑 ChatGPT: 8/10

ChatGPT didn't mess around. It gave a practical, day-by-day breakdown with clear deliverables, e.g.:

  • Week 1 deliverables: Updated resume and LinkedIn profile; target company list; membership in PM communities; and a proof-of-work project plan.

  • Week 2 deliverables: 15-20 tailored applications; 10-15 new LinkedIn connections; and a published proof-of-work piece showing your skills.

The best part?

A detailed "Networking Without a Strong Network" section with specific tactics and honest pros/cons for each approach. This included:

  • Using PM communities like Mind the Product and ProductCoalition to build relationships before asking for anything

  • Commenting on thought leader posts with genuine insights (not generic "great post!" responses)

  • Creating content that demonstrates your PM thinking, which naturally attracts connections

Here’s where it droppd the ball: ChatGPT skipped market research before jumping into resume updates.

This. Is. Important.

You can't tailor your materials if you don't know what companies actually want.

🏅 Claude: 7.5/10

Claude nailed the fundamentals. It started with market research FIRST, then moved to positioning.

It asked smart follow-up questions no other model did:

  • What company stage/type do you want?

  • Geographic flexibility?

  • Product domain focus?

Claude also gave a brutal 2024-2025 market context and compensation benchmarks. No sugar-coating the state of the market. I thought this was a brilliant addition to the plan.

The contingency plans were gold, too. If you're not getting responses after Week 2, Claude offered three backup approaches:

  • A/B test different LinkedIn message templates with specific variables to test

  • Shift from PM roles to adjacent roles (growth manager, customer success) with clear positioning

  • Add technical case studies to your portfolio with templates for what to include

🤔 The Disappointments: Manus Stumbles, Gemini Bombs

🆗 Manus: 6/10

Manus jumped straight to "positioning and branding" without market research. It told you to spend 80% of Week 1 on positioning but never mentioned understanding market demand first.

It also gave an hour-by-hour breakdown, which was way too detailed. Nobody needs that level of micromanagement.

One bright spot: Manus provided a solid cold email template.

I read it and immediately thought: “Oh, this would work.”

(I share the email below.)

🗑️ Gemini: 3/10

Gemini's output was practically unreadable. Instead of clear advice, it gave me section headers like:

  • "The 30-Day Product Management Velocity Strategy: Maximizing Offer Conversion Under Constraint"

  • "Framework Mastery for Cognitive Efficiency (Days 11-13)"

What I think it’s trying to say in Plain English: practice talking about your work. Why not just say that?

Gemini obsessed over proof-of-work projects while ignoring market research and networking. It put negotiation tactics before you even had interviews. Cart, meet horse.

The one thing Gemini got right: focus on one specific role instead of spraying applications everywhere.

🎯 The Best Tactics to Steal from Each Model

Each AI had at least one killer recommendation worth using. Here's what to take from each:

ChatGPT's "Networking Without a Strong Network" section was the most practical guide I've seen.

👉 Here's the framework:

Week 1-2: Build visibility

Join 3-5 PM communities (ProductCoalition, Mind the Product, Product School)

Comment thoughtfully on 5 posts per day from industry leaders

Share one insight or observation weekly that shows your thinking

Week 2-3: Create value first

Offer to review someone's product roadmap or do a mini teardown

Write a post solving a common PM problem you've faced

Participate in community discussions without asking for anything

Week 3-4: Make specific asks

Reach out to people you've engaged with consistently

Reference specific conversations or shared interests

Ask for 15-minute informational chats, not job referrals

Claude's backup plans were brilliant because they gave you clear decision points.

👉 Contingency plans

After Week 1: Check your materials

If zero profile views: your LinkedIn headline is invisible to recruiters

If views but no messages: your experience section doesn't match what hiring managers want

If messages but wrong roles: your positioning is unclear

After Week 2: Check your outreach

If zero responses to cold emails: A/B test subject lines and opening hooks

If responses but no meetings: your ask is too vague or too big

If meetings but no interviews: you're not demonstrating enough value in conversations

After Week 3: Pivot strategy

Consider adjacent roles that value your PM skills

Double down on proof-of-work instead of applications

Focus networking efforts on smaller companies with faster hiring

From Manus: The Cold Email That Actually Works

👉 Use this cold email

Hi [Name], I've been following [Company Name]'s work in [specific area, e.g., AI-driven analytics] and was particularly impressed by [mention a specific product/feature or recent achievement]. As a Product Manager with 2 years of experience in [your area of expertise, e.g., B2B SaaS platforms], I'm keen to learn more about how your team approaches [specific PM challenge or domain]. I'd love to connect and potentially hear your insights on the PM landscape at [Company Name] when you have a moment. Best, [Your Name]

Why does this work?

  1. Show you've done research (specific product/feature)

  2. Establish credibility (your relevant experience)

  3. Express genuine curiosity (what you want to learn)

  4. Make a small ask (insights, not a job)

Send this exact template to 5 people this week. Customize the bracketed sections. Track your response rate.

Buried in Gemini's jargon was one smart insight: commit to one specific role identity for at least 10 working days.

Instead of applying to "Product Manager," "Growth Manager," "Product Marketing Manager," and "Strategy Manager" all at once, pick ONE. Tailor everything to that identity:

  • Your LinkedIn headline

  • Your resume positioning

  • Your portfolio projects

  • Your outreach messages

  • Your community participation

After 10 days, if you're getting zero traction, pivot to a different specific role. But give each position enough time to generate signal.

💫 The Bottom Line

ChatGPT and Claude are your best bets for creating a job search plan. This week, ChatGPT wins on tactical execution, Claude wins on strategic thinking.

But the way you keep winning?

Keep testing different models and tools to give you that edge on your job search.

You got this.

I love meeting new people. Say hi on LinkedIn 👋

🤝 When you’re ready, here are 2 ways I can help you land your next job:

1/ Land The Interview Resume Service - I fix your resume, LinkedIn, and cover letter so you stop getting ghosted and start getting responses. No more wondering why your applications disappear into black holes. Just marketing materials that work.

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2/ Get personalized career coaching. Want to accelerate your remote job search? I'll work directly with you in my high-touch group coaching program. You'll get resume reviews, outreach message editing, interview feedback, and more, to help you land your dream remote role. Only 1 spot remaining. Sold out — join the waitlist.

🚪 Looking for a remote job?

👟 Speed wins. Yesterday morning at 9:37 ET I hand-picked the newest open remote roles before they get flooded with applications. Get exclusive early access to these open roles.

🎯 Product Roles

📣 Marketing Roles

  • Manager, Marketing Operations at Sony Interactive Entertainment 🇺🇸 Apply Here

  • Principal PM, Marketing Automation at Zalando 🇩🇪 Apply Here

  • Sr Marketing Manager at Afterpay 🇺🇸 Apply Here

  • Marketing Manager at Vive Health 🌎 Apply Here

  • Lead PMM at Jobgether 🇵🇱 Apply Here

  • Sr Marketing Manager at Storm2 🇺🇸 Apply Here

  • Email Marketing Manager at Superpower 🇺🇸 Apply Here

  • Events Marketing Manager at CoderPad 🇺🇸 Apply Here

  • Marketing Manager at Caramel Talent 🇬🇧 Apply Here

  • PMM at Pindrop 🌎 Apply Here

  • Marketing Manager at YourPrime 🇬🇧 Apply Here

🤩 Customer Success Roles

That’s a wrap. See you next week 👋

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