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

Waves 0 – 4 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, filters by salary and relevance using a config-driven allowlist, and uses a 53-bullet master resume database to select the most relevant content for each role.

Python 3 Claude API Adzuna API NewsAPI python-docx pandas BeautifulSoup AWS S3 Git
# Configure search in search_config.json # titles, locations, filters — all in one place
# Run the scraper $ python3 job_scraper.py ✓ 42 jobs found · 18 passed filters ✓ Saved: job_listings_2026-05-17.xlsx
# Tailor resume to a specific role $ python3 resume_tailor.py \ --company "Fidelity" \ --url "https://linkedin.com/..."
# Generate submission-ready 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
Config-driven job search via Adzuna API. Filters by salary, recency, job type, and title allowlist. Outputs to dated Excel.
Complete
2
AI Resume Tailor
Claude API reads job description, selects best-fit bullets, rewrites summary, generates Word doc. 93/100 match score.
Complete
2.5
Company Intelligence
Enriches shortlisted roles with company background, recent news, and industry data via Wikipedia and NewsAPI.
Complete
3
HTML Job Report
Generates a formatted HTML report of enriched listings with company briefs and one-click resume tailor commands.
Complete
4
Portfolio Site
This site — documenting the project, the journey, and the build. Hosted on AWS S3 with Route 53.
Complete
5
Application Tracker
SQLite database to track applications from submission through offer. Dashboard to monitor pipeline status.
Planned
6
Expanded Search
Additional job source integrations for broader, fresher listings across more platforms.
Planned

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.