←Back to kills
Pipeline Rebuild—2025—2 weeks
SERIES B STARTUP
A $30M startup with a CI/CD system held together by prayers and a server literally under someone's desk.
GitHub ActionsDockerTerraformAWS
🪓KILLED: Jenkins nightmare
THE DISEASE
Jenkins instance so old it remembered MySpace. 200 plugins, half abandoned, running on hardware that predated the company. Deployments were a team sport.
✕Jenkins with 200 plugins (47 deprecated)
✕Server under Dave's desk (Dave left)
✕45-minute deployment times
✕Nobody knew the admin password
✕"Have you tried restarting Jenkins?" was the daily standup
THE SURGERY
01
Extraction
Reverse-engineered the Jenkins pipelines. Found 3 that did absolutely nothing.
02
Containerization
Dockerized the entire application stack. No more "works on my machine."
03
Infrastructure
Terraform for AWS infrastructure. Version controlled, repeatable, sane.
04
Actions
GitHub Actions pipelines that a junior dev could understand and maintain.
THE AFTERMATH
Deployments went from a prayer to a button click. The desk under which the server lived is now just a desk.
Deployment time
45 min→4 min
Deploy frequency
1x/week→10x/day
Failed deploys
30%→< 1%
Team morale
💀→🚀
"
We used to schedule deploys around Dave's lunch break so we wouldn't kick his desk. That's not a joke.
CTO
Series B Startup