Day 3 of 28 · AI Job Hunt

Your AI Job Hunt Toolkit

⏱ 5 min 📊 Beginner

Yesterday you discovered that your experience is worth more than you thought. Today, you're going to set up the AI tools that will power your entire job search — from resume writing to interview prep.

You don't need a dozen tools. You need the right three or four, and you need to know exactly when to use each one.

The right AI tool for each stage of your job search.

The core toolkit

ChatGPT — Your primary writing and brainstorming partner. Use it for resumes, cover letters, LinkedIn content, interview prep, and salary research. The free version works for most tasks. The paid version gives you GPT-4 and longer conversations.

Claude — Your deep analysis and editing partner. Claude excels at reviewing your resume for inconsistencies, analyzing long job descriptions, and giving honest feedback on your materials. It's particularly good at nuanced writing tasks where tone matters.

Perplexity — Your research engine. Use it for company research, salary data, industry trends, and finding information about interviewers. Unlike regular AI, Perplexity searches the web in real-time and cites its sources.

LinkedIn — Not AI-powered in the same way, but essential. Your profile is your public resume, and AI will help you optimize every section of it.

Knowledge Check

Which AI tool is best for real-time company research with cited sources?

A

B

Claude

C

ChatGPT

D

Perplexity

Perplexity searches the web in real-time and provides cited sources — making it perfect for researching companies, salary ranges, industry trends, and interviewer backgrounds. ChatGPT and Claude are powerful for writing and analysis, but they don't search the live web in the same way.

When to use which tool

Here's your cheat sheet for the next 28 days:

Resume writing and tailoring → ChatGPT or Claude. Both are excellent. ChatGPT is faster for quick drafts; Claude is better for careful editing and tone.

Cover letters → ChatGPT. It's the fastest at generating personalized letters once you give it the right context.

Company research → Perplexity. "Tell me about [company] — recent news, culture, challenges, and what they look for in hires."

Interview prep → Claude for generating questions and analyzing your answers. ChatGPT for mock interviews and rapid-fire practice.

Salary research → Perplexity for current market data. ChatGPT or Claude for negotiation strategy and scripts.

LinkedIn optimization → ChatGPT for rewriting sections. Claude for reviewing the overall narrative.

Networking messages → ChatGPT for drafting personalized outreach. Short, direct, and specific.

🤖

ChatGPT

online

I'm setting up my AI toolkit for job hunting. Give me the single best tip for getting good results from AI throughout my search.

**Always give context before asking for output.** The #1 mistake job seekers make with AI is asking generic questions: ❌ "Write me a resume" ❌ "Help me prep for an interview" Instead, front-load your context: ✅ "I'm a marketing coordinator with 4 years of experience applying for a Senior Marketing Manager role at Stripe. Here's the job description: [paste]. Here's my current resume: [paste]. Tailor my resume to this specific role." The more context you provide — your background, the specific role, the company, the job description — the better the output. Every time. Think of it like briefing a really smart assistant. The better the brief, the better the work.

↻ Replay conversation

Knowledge Check

What's the most important habit for getting great results from AI during your job search?

A

Ask short, simple questions to save time

B

Copy and paste AI output without editing

C

Always provide context — your background, the specific role, the job description, and the company — before asking AI to generate anything

D

Use the most expensive AI subscription available

Context is everything. "Write a cover letter" gives you generic slop. "Write a cover letter for a Senior PM role at Shopify — here's the JD and my background" gives you something a recruiter actually wants to read. The 60 seconds you spend adding context saves you 30 minutes of editing.

Setting up your workflow

Here's how to organize your job search with AI. Create a simple system:

Step 1: Create a "master document." Paste your full work history, skills, achievements, and the results from yesterday's skills assessment into one document. This is your AI briefing doc — you'll paste it at the start of every new conversation.

Step 2: Save job descriptions. Every time you find an interesting role, copy the full job description. You'll feed these to AI for resume tailoring, cover letter writing, and interview prep.

Step 3: Keep a research folder. When AI gives you company research or interview prep, save it. You'll reference it later.

Step 4: Track your applications. A simple spreadsheet: Company, Role, Date Applied, Status, Notes. Ask AI to create a template for you.

This takes 15 minutes to set up and saves you hundreds of hours over the course of your search.

Final Check

Why should you create a "master document" with your full work history for AI?

A

Because AI requires a document to function

B

So you can memorize your resume

C

So you can quickly paste it into any AI conversation to give instant context — making every resume, cover letter, and prep session personalized and accurate

D

So AI can post it to job boards for you

Your master document is your AI briefing file. Instead of re-explaining your background every time you start a new conversation, you paste it in and say "here's my background — now help me with X." It's the single biggest time-saver in an AI-powered job search.

🛠️

Day 3 Complete

"The right tools in the right order turn job hunting from a marathon into a sprint. Set up once, use everywhere."

Tomorrow — Day 4

Finding Your Target Role

Tomorrow you'll use AI research to find the specific roles where your skills are most valuable.

Continue to Day 4 →