I don't just manage projects. I build them.
20 years delivering software. Recently back to hands-on
building, learning AI by doing. The results have been
surprising, even to me.
A job search tool I built for myself — and the first real AI project
I have built and actually use. It surfaces relevant listings, gives me the company
intelligence I need to decide whether to apply, and then handles the
time-consuming parts: selecting the right resume bullets and drafting
a cover letter. I stay in the loop at every step.
The pipeline scrapes job boards across multiple titles and locations,
then I review each listing and mark the roles I want to pursue. For
those roles, the system pulls company background, news, and a
Claude-generated match score that compares the job description against
my full 57-bullet resume database. I use that score to decide whether
to move forward. When I do, Claude selects the best-fit bullets and
drafts both a tailored resume and a voice-matched cover letter — both
as editable Word documents I review and refine before anything goes out.
Python 3Claude APIStreamlitJSearch API (OpenWeb Ninja)NewsAPIDuckDuckGopython-docxpandasAWS S3Git
# Launch the dashboard — runs the whole pipeline$ streamlit run dashboard.py✓ Control panel live at localhost:8501# ...or run each stage from the command line$ python3 job_scraper.py✓ 42 jobs found · 18 passed filters✓ Job descriptions captured for each posting✓ Saved: job_listings.xlsx# Tailor resume to a specific role (JD auto-filled from Excel)$ python3 resume_tailor.py \
--company "Fidelity" \
--title "IT Delivery Manager" \
--description "..."✓ Match score: 93 / 100✓ Bullets selected and summary rewritten# Generate submission-ready Word doc$ python3 resume_generator.py \
--input output/tailored_Fidelity.json✓ Resume saved: Jason_Darrow_Resume_Fidelity.docx# Generate voice-matched cover letter$ python3 cover_letter_generator.py \
--company "Fidelity" \
--title "IT Delivery Manager" \
--description "..."✓ Cover letter saved: CoverLetter_Fidelity.docx
Build Log — AI Job Search
0
Resume Database
Structured master resume in JSON — 57 bullets tagged by skill, strength scored, ready for AI selection.
Complete
1
Job Scraper
Config-driven job search via JSearch API (OpenWeb Ninja). Captures full job descriptions at scrape time. 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 DuckDuckGo and NewsAPI. Claude API scores each role against the master resume (0–100 match) and displays the badge in the HTML report.
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
Streamlit Dashboard
Browser control panel for the whole pipeline. Each stage runs from a button with live logs; review and tailor without touching the terminal.
Complete
6
AI Cover Letter Generator
Claude API generates a voice-matched cover letter grounded in the same bullets selected for the tailored resume. Writing rules, anti-AI guardrails, and before/after examples embedded directly in the prompt. Outputs a submission-ready .docx.
Complete
7
Application Tracker
Notion API integration to track applications from submission through offer — synced from the pipeline automatically.
Planned
8
Expanded Search
Additional job source integrations for broader, fresher listings across more platforms.
Planned
Second Project
Getting Things Done with AI
What I Built
A full-stack personal weekly planner — built from scratch because nothing I tried
kept calendar, habits, and weekly goals in one place without a subscription.
This runs on a Linux box in my home office and is accessible from any device on the network.
The app is an Outlook-style weekly organizer with a full time grid, all-day events,
recurring events, and per-category color coding. Below the calendar sit three weekly
planning cards: a free-text Weekly Summary, a Daily Routine habit tracker with
checkboxes across all seven days, and three SMART Goals scoped to the current week.
All data persists to a local SQLite database via a Next.js API layer.
Theme switches between Light and Graphite. Built with Claude Code.
# Run locally$ npm run dev✓ Ready in 1305ms→ http://localhost:3000# Deploy to Linux server under PM2$ rsync -av --exclude node_modules --exclude .next \
gtd-app/ darrowj@192.168.1.246:~/gtd-app/$ ssh darrowj@192.168.1.246 \
"cd ~/gtd-app && npm install && npm run build && pm2 start npm --name gtd -- start"✓ App running — accessible from any device on the network→ http://192.168.1.246:3000
Build Log — Getting Things Done with AI
1
Full Calendar UI + SQLite Persistence
Week view and Day view with time grid (6 AM–10 PM), all-day band, recurring events (daily / weekly on chosen days), overlapping event layout, and per-category color coding. Event modal with all-day toggle, repeat weekday chips, reminder settings, and "save this occurrence vs. save all" for recurring edits. Planning panel with Weekly Summary, Daily Routine habit tracker, and SMART Goals — all scoped per week. Light and Graphite theme toggle. All data persists to SQLite via Next.js API routes and Drizzle ORM.
Complete
2
Linux Deploy
Sync to Ubuntu home server, run under PM2 with startup hook. Accessible from any device on the local network.
In Progress
3
Integrations
Google Calendar sync to pull live events into the week view. Notion task pull to surface open next actions alongside the schedule.
Planned
4
AI Features
Claude API morning briefing integrated into the app. Weekly review assistant that processes captures and suggests next actions. SMART goal suggestions based on the week summary.
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, and the ones that followed.
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 MIS — 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.
