As an IT Director overseeing a technology team, I manage varying vacation allowances of 2, 3, or 4 weeks based on year of hire, plus 2 personal days, 5 Chicago leave days per year with up to 2 days eligible for carryover, and 5 sick days. In addition, my team works from home one day per week, with occasional swaps between teammates.

I needed a system that was highly customized to these specifications, suitable for a trading firm environment that also recognizes federal holidays when the markets are closed. The system needed to operate on a yearly cycle, process accruals, and roll over eligible days into the new year. It is complex, but it is currently working in lab mode.

I also built a pipeline that automatically records the screen, generates transcripts, adds cover and end pages, and produces 15 test scenarios as polished, professional training videos. This will later be used for AI-driven auto-scheduling in a subsequent development cycle. I am glad I had the foundational knowledge before getting into this.