Day 14 of 28 · AI Job Hunt

Your Application Machine

⏱ 5 min 📊 Beginner

Two weeks in. You've built a skills assessment, a career story, an ATS-optimized resume, a LinkedIn profile that attracts recruiters, and a portfolio of case studies. Now it's time to assemble everything into a repeatable system that produces high-quality, tailored applications at speed.

Your Application Machine — Find Role, Tailor Resume, Custom Cover Letter, Submit, Track, Follow Up

Quality applications at scale — the complete workflow.

The 25-minute application workflow

Here's the complete workflow for submitting a tailored, high-quality application. Once you build the habit, this takes about 25 minutes per application.

Minutes 1-2: Decode the JD. Paste the job description into AI. Get the must-haves vs. nice-to-haves, the extracted keywords, and the hidden problem they're hiring to solve.

Minutes 3-10: Tailor your resume. Paste your master resume and the JD. Ask AI to tailor the experience bullets, add missing keywords, and adjust the summary. Review and finalize.

Minutes 11-15: Write the cover letter. Feed AI your background and the JD. Generate a 150-200 word cover letter with a company-specific hook. Review and tweak.

Minutes 16-20: Quick company research. Use Perplexity to find recent news, funding, product launches, and culture insights. Save these notes — you'll need them for interview prep later.

Minutes 21-25: Submit and track. Submit the application. Add it to your tracking spreadsheet: company, role, date, status, key contact, notes.

That's it. Five steps, 25 minutes, and every application is personalized.

Knowledge Check

Why is 25 minutes per application better than 5 minutes?

A

It isn't — faster is always better

B

Because a tailored 25-minute application has a 15-25% callback rate vs. 2-5% for a generic 5-minute application — you get more callbacks from fewer applications

C

Because applications have a minimum time requirement

D

Because hiring managers can tell how long you spent

It's about return on time invested. Five generic applications (25 minutes total) might get you 0-1 callbacks. Five tailored applications (125 minutes) might get you 1-3 callbacks. The targeted approach is 3-5x more efficient even though each application takes longer.

🤖

ChatGPT

online

I want to apply to 5 jobs today. Here's my master resume and the 5 job descriptions. For each one, give me: 1) The 3 most important keywords I'm missing, 2) A tailored resume summary, 3) A 150-word cover letter. Let's do them all.

I'll work through all 5. Here's the format for each: **Job 1: Product Marketing Manager at Stripe** Missing keywords: "payments ecosystem," "developer marketing," "self-serve growth" Tailored summary: "Product marketing leader with 5 years in B2B SaaS, specializing in go-to-market strategy and developer-focused positioning. Led 3 product launches driving 28% average feature adoption. Experienced in translating complex technical products into compelling market narratives." Cover letter: "I've spent the last 5 years making technical products feel simple — which is exactly what Stripe does for payments. In my current role, I own go-to-market strategy for a developer-focused platform, and my last launch drove 28% adoption in Q1. What excites me about Stripe is the intersection of technical depth and market clarity — your developer docs are already legendary, and I'd love to bring that same clarity to your broader product marketing. I bring cross-functional launch experience, a content engine driving 45% of pipeline, and a genuine belief that the best product marketing makes complex things feel obvious. I'd welcome a conversation about how I can contribute to Stripe's next chapter." [Continuing with Jobs 2-5...] Shall I continue with the remaining four?

↻ Replay conversation

Your daily job search schedule

Structure your job search like a job itself. Here's a proven daily schedule:

Morning (1 hour): Apply.

Submit 3-4 tailored applications using the 25-minute workflow. Quality over quantity.

Midday (30 minutes): Network.

Send 3-5 personalized LinkedIn messages (you'll learn how in Week 3). Comment on 5 posts from people at target companies.

Afternoon (30 minutes): Build visibility.

Draft or schedule one LinkedIn post. Update your tracking spreadsheet. Follow up on pending applications.

That's 2 hours per day. At 3-4 applications per day, you'll have 15-20 highly targeted applications out per week — each one significantly more likely to generate a callback than a generic blast.

Knowledge Check

How many tailored applications per day is a realistic, high-quality target?

A

20+ — spray and pray

B

10-15 — more volume always wins

C

1 — you should only apply to one job per day

D

3-4 — enough volume to build momentum, with enough time per application to maintain quality

Three to four tailored applications per day hits the sweet spot: enough volume to generate consistent callbacks (15-20 per week), with enough care per application to maintain the 15-25% callback rate that tailoring provides. More than that and quality drops. Fewer and momentum stalls.

The Week 2 scorecard

Let's review what you built this week:

Day 8: An AI-optimized resume with quantified achievements and keyword-matched bullets.

Day 9: ATS mastery — you know exactly how to format and keyword-optimize for the bots.

Day 10: A cover letter system that produces personalized letters in 3-5 minutes each.

Day 11: A LinkedIn profile that actively attracts recruiters with an optimized headline, About section, and skills.

Day 12: A LinkedIn content strategy that positions you as an expert in your field.

Day 13: A portfolio of 3-5 case studies that prove your impact.

Day 14: A complete application machine that produces tailored applications in 25 minutes.

You now have better job search materials than 95% of candidates. Week 3 is where you go on the offensive — networking, outreach, and interview prep.

Final Check

What separates your application system from what most job seekers do?

A

You skip cover letters to save time

B

Every application is tailored to the specific role and company — resume, cover letter, and keywords are customized for each opportunity in just 25 minutes

C

You apply to more jobs than anyone else

D

You use fancier fonts and formatting

Personalization at scale is your superpower. Most job seekers send the same resume to 200 companies and get 2 callbacks. You send a tailored application to 20 companies and get 5 callbacks. Same total effort, dramatically better results.

⚙️

Day 14 Complete

"You've built a machine. Every application that comes out of it is sharper, faster, and more targeted than what 95% of your competition is sending. Now let's go on the offensive."

Tomorrow — Day 15

AI-Powered Company Research

Week 3 starts — you'll learn to research companies so thoroughly that interviewers think you already work there.

Continue to Day 15 →