Principal software engineer in the Denver area. I spent the last five years at Papaya Pay on the systems that pay people's bills: 50,000+ bill submissions a month, moved through virtual cards, ACH and an AI voice agent. Most of my work was changing those systems while people were using them, so I write a lot about modernizing without rewriting.
Case studies (the long versions, with the decisions and the numbers): isaacaskew.com/work
- Switching sponsor banks without a rewrite
- Making automatic refunds safer
- Bringing an AI voice agent in-house
- Digital Presentment: paying medical bills from a text message
- Five years of cleaning up a legacy PHP portal
Things I've shipped
- VenuNite: a hyperlocal events API with iOS and Android apps, a website and an MCP server. On the App Store since May 2026.
- Tern: open source, self-hosted marketing automation (pre-1.0).
Podcast and book
- Never Rewrite, 175+ weekly episodes with Jeffrey Sherman on software modernization and engineering culture.
- The Rewrite Trap, why software rewrites fail and what to do instead.
Most of my day-to-day work lives in private repositories. Resume and contact: isaacaskew.com · LinkedIn