AI for the Job Hunt

Job hunting is a full-time job that nobody trains you for. You spend hours tailoring resumes, writing cover letters, filling out the same information in twelve different applicant tracking systems, and researching companies before interviews. Most of this work is repetitive, formulaic, and soul-crushing. So I built tools to handle the soul-crushing parts, and kept the human parts for myself.

Grant Writer Redux

This one started as a tool for actual grant writing — generating first drafts of grant applications based on a template, a project description, and the funding organization’s priorities. But I quickly realized the same architecture worked for job applications. A job posting is just a grant RFP with different jargon: instead of “organizational capacity” you have “relevant experience,” and instead of “proposed outcomes” you have “what you’ll accomplish in the first 90 days.”

Grant Writer Redux takes three inputs: my resume/CV, the job posting or grant RFP, and any additional context (the company’s recent news, their stated values, specific projects I want to reference). It generates a tailored cover letter and, for grant applications, a full narrative section. The output isn’t a finished product — it’s a strong first draft that I can refine in 15 minutes instead of writing from scratch in two hours.

The key to making this work is specificity. Generic cover letters are obvious and ineffective. The AI needs enough context to write something that feels genuinely personal: referencing specific programs the organization runs, connecting my experience to their stated needs, and using language that matches their communication style. I feed it their website, their recent blog posts, their annual report if it’s available. The more context, the better the output.

Application Completer

If you’ve applied for more than five jobs online, you know the pain. Every applicant tracking system wants the same information in a slightly different format. Your name, your address, your work history (in reverse chronological order, unless they want chronological order), your education, your skills, your references. You’ve already put all of this in your resume, but the system wants you to type it again into individual fields.

Application Completer stores my information in a structured JSON file and uses AI to map it to whatever fields a given application presents. It handles the common ATS platforms (Workday, Greenhouse, Lever, iCIMS) and can adapt to custom forms by interpreting field labels and matching them to the right data. It also handles the annoying edge cases: date formats that differ between systems, phone number formatting, and the perennial question of whether “state” means the abbreviation or the full name.

This doesn’t fully automate the application process — it still requires my review and submission. But it takes a 45-minute application and turns it into a 10-minute review, which means I can apply to more positions without burning out.

CompanyResearch

The interview is where the job hunt gets interesting, and it’s where preparation makes the biggest difference. CompanyResearch is a tool that generates a comprehensive briefing document about a company before an interview. It pulls from the company’s website, recent news articles, SEC filings (for public companies), Glassdoor reviews, LinkedIn profiles of your interviewers, and any relevant industry reports.

The output is a structured document with sections on company overview, recent news and initiatives, the team you’d be joining, potential challenges the company faces, and suggested questions to ask. It also identifies connections between my experience and the company’s current priorities — “they’re expanding their grants program, and you managed a $17M grant initiative” — which gives me concrete talking points.

The AI’s ability to synthesize information from multiple sources is the real value here. I could do all this research manually, but it would take 2-3 hours per company. The tool does it in about 10 minutes, which means I can be thoroughly prepared for every interview instead of just the ones I have time to research.

The Ethics of AI in Job Hunting

I think about this a lot. Am I gaming the system? Is it unfair to use AI tools that other candidates might not have access to?

My honest answer is: the job application system is already broken, and these tools level a playing field that was never level to begin with. Companies use AI to screen resumes. ATS systems reject candidates based on keyword matching. Recruiters spend an average of 7 seconds reviewing each resume. The process is designed for efficiency, not fairness, and it disadvantages people who can’t afford to spend 40 hours a week on applications.

My tools don’t lie on my behalf. They don’t fabricate experience or inflate qualifications. They take my real experience and present it in the format the system expects, adapted to each specific opportunity. That’s not gaming the system — it’s speaking the system’s language.

And critically, everything the AI generates goes through my review. I read every cover letter, verify every data point in every application, and prepare for every interview using the research as a starting point, not a script. The AI handles the format. I handle the substance.

What Actually Works

After using these tools across dozens of applications, here’s what I’ve found: the cover letter tool has the highest impact. A genuinely tailored cover letter that references specific aspects of the company and role gets responses. The application completer saves the most time. The research tool makes the biggest difference in interviews, where being able to reference the company’s Q3 initiative or their recently published strategic plan shows a level of preparation that interviewers notice.

The combination of all three means I can run a more effective job search in 10 hours a week than I could previously run in 30. The saved time goes to networking, skill development, and the kind of deep preparation that no tool can automate.

The modern job hunt is a process optimization problem. These tools are my process optimization. They’re not a shortcut — they’re a more efficient path to the same destination.