IT Leader · AI Builder · US Air Force Veteran

Jason
Darrow

I'm a builder — in the real world and the virtual one. 20 years delivering software. Recently back to hands-on building, learning AI by doing. The results have been surprising, even to me.

Background
Delivering IT Solutions for 20 Years
Current Project
AI Job Search System
Stack
Python · Claude API · AWS
Status
Actively Building

Wave 1 – 2 Complete

AI Job Search System

What I Built

A personal AI agent that finds job listings, scores them against my experience, tailors my resume for each role using the Claude API, and generates a submission-ready Word document — all from the command line. Built to solve my own job search problem while learning AI development.

The system scrapes multiple job boards across multiple locations, enriches listings with company intelligence, and uses a 53-bullet master resume database to select the most relevant content for each role.

Python 3 Claude API JSearch API NewsAPI python-docx pandas BeautifulSoup Git
# Find jobs across locations $ python3 job_scraper.py \ --titles "IT Delivery Manager" "Program Manager" \ --locations "Boston MA" "Worcester MA"
# Tailor resume to a specific role $ python3 resume_tailor.py \ --company "Fidelity" \ --url "https://linkedin.com/..."
# Generate Word doc $ python3 resume_generator.py \ --input tailored_Fidelity.json
✓ Match score: 93 / 100 ✓ Resume saved: Jason_Darrow_Resume.docx

Build Log

Project Progress

0
Resume Database
Structured master resume in JSON — 53 bullets tagged by skill, strength scored, ready for AI selection.
Complete
1
Job Scraper
Multi-location, multi-title job search across job boards. Outputs to Excel with company enrichment via NewsAPI.
Complete
2
AI Resume Tailor
Claude API reads job description, selects best-fit bullets, rewrites summary, generates Word doc. 93/100 match score.
Complete
3
Application Tracker
SQLite database to track applications from submission through offer. Dashboard to monitor pipeline status.
Coming Soon

Background

About Me

I spent 20 years building and delivering software — starting as a web application architect at Bank of America, where I built systems responsible for billions in managed assets, and progressing to IT Delivery Manager at Voya Financial overseeing programs from $250K to $3M.

Instead of just sending resumes right away, I decided to build the tool I wished existed — an AI system that finds relevant jobs, tailors my resume to each one, and tracks my progress. This site documents that project.

I'm learning AI by doing, not watching. Every week something new gets built, committed to GitHub, and added to the system. The results have been genuinely surprising.

🎓
Education
MS Information Systems — Bentley College (Distinction)
BS Management of Information Systems — Northeastern University (Magna Cum Laude)
📋
PMP · CSM Certified
Project Management Professional · Certified ScrumMaster
🛩️
US Air Force Veteran
Senior Airman · Honorable Discharge
🥋
BJJ Black Belt
Brazilian Jiu-Jitsu — the hardest thing I've ever done

Get In Touch

Let's Talk

I'm currently open to IT Delivery Manager, Program Manager, and AI Operations roles in the Greater Boston area and remote.

If you're building something interesting with AI, or know someone who needs a delivery leader who can actually build — I'd love to hear from you.