Shutterfly was facing challenges in 2017 with outdated legacy systems that made improving customer experiences costly and time-consuming. They wanted to upgrade their ecommerce platform and tools but could not afford the large investment. Instead, they started using machine learning to personalize customer experiences like website content and email promotions. This provided a scrappy solution that drove engagement and eventually revenue increases without requiring significant technology changes. Some lessons learned were that cross-functional collaboration takes time, testing is important for machine learning, supporting extra work from teams is key, and data science skills can be developed in non-traditional employees.