The speaker discusses how Lookout has scaled its engineering organization and technical infrastructure over time. In 2011, Lookout had problems with unreliable deployments and a monolithic codebase. It introduced new tools like JIRA, Jenkins, and Git/Gerrit to improve its workflow. It also automated deployments and now has a much higher success rate. As Lookout has grown, it has moved to a more distributed architecture with over 100 microservices running on different technologies. Scaling organizational knowledge and coordinating many independent services will be ongoing challenges.