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

Because applications have a minimum time requirement

B

Because hiring managers can tell how long you spent

C

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

D

It isn't — faster is always better

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

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

B

1 — you should only apply to one job per day

C

10-15 — more volume always wins

D

20+ — spray and pray

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

You use fancier fonts and formatting

C

You apply to more jobs than anyone else

D

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

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 →