Building AI That Actually Works — Jessica Collier on Spot, Evernote, and the Future of Workplace Incident Management

In this episode of The Bridge, Justin sits down with Jessica Collier, CEO of Spot, and founding partner of All Turtles, to explore her journey from academia to building one of the most thoughtful AI-driven tools in the HR tech space. Jessica was the first UX writer at Evernote, where she helped shape user experiences through words before it was a recognized craft. She later went on to co-found All Turtles, alongside Phil Libin (former Evernote CEO) and Jon Cifuentes, with a mission to build practical AI applications — long before the current hype cycle. In this conversation, Jessica shares:The early days of bringing AI into product workflows before it was coolHow Spot is reshaping the case management and incident reporting category with anonymous, AI-powered reporting tools for any case typeWhy “trust” is the foundation of any product solving sensitive problemsThe build vs. partner decision framework when enhancing core functionalityLessons from scaling multiple ventures rooted in ethical product design Whether you"re an operator building with AI, a founder evaluating product scope, or someone navigating tough conversations in the workplace — this episode offers tactical insights and big-picture clarity.