Five Years as a Startup CTO: How, Why, and Was It Worth It?

A CTO reflects on five years leading technology at an early stage startup, from inheriting a broken Salesforce implementation to building a 20+ person engineering team and custom SaaS platform. The journey involved migrating from Salesforce to a custom stack (AWS, Kubernetes, Golang, React), establishing effective team structures across platform, backend, frontend, QA and design, and learning crucial lessons about technical leadership, hiring, remote work, and maintaining work-life balance during the startup grind.