Senior Software Engineer, Actionable Intelligence
A little about us…Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations. Transportation technology is a hot market, and we’re leading the charge with raving fans and new customers signing up every day. We raised $450M in our Series D funding round in March of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation! More about our team and company: Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg Our careers page: https://www.fleetio.com/careers Description We’re looking for a Senior Software Engineer to join our Actionable Intelligence Team, with a focus on building product experiences that help customers understand what is happening in their fleet and take the next best action. The Actionable Intelligence Team is building the next generation of intelligent, customer-facing workflows in Fleetio. Our squad is currently working on Service Advisor, and we’re continuing to explore new AI tools that surface insights, reduce manual work, and help customers make faster, more confident decisions inside the product. More About Our Team and Company Watch our culture videos: https://fleet.io/culture Engineering culture, interview process and videos: https://www.fleetio.com/careers/engineering Fleetio overview video: https://www.youtube.com/watch?v=IlvIbwZT3oU Fleetio Go overview video: https://www.fleetio.com/go More about the Fleetio platform: https://www.fleetio.com/features API docs: developer.fleetio.com Test drive Fleetio to get an even better feel for what we're building: https://www.fleetio.com/register This is a remote opportunity and is open to candidates in the United States, Canada, or Mexico. The Actionable Intelligence Team is building the next generation of intelligent, customer-facing workflows in Fleetio. Our squad is currently working on Actionable tools powered by AI that surface insights, reduce manual work, and help customers make faster, more confident decisions inside the product. This is a senior full-stack role for someone who is a strong Ruby on Rails engineer and deeply passionate about front-end best practices, user experience, and modern React development. You’ll help us build AI-enabled features that are not only technically sound but also easy to understand, trustworthy, measurable, and valuable to customers. The ideal candidate is comfortable moving from ambiguous product opportunities to rapid prototypes, then hardening successful experiments into reliable product capabilities. Fleetio’s AI engineering expectations emphasize translating ambiguous AI opportunities into clear experiments, balancing user value with technical feasibility, and creating feedback loops through customer feedback, usage signals, evaluations, and quality reviews Your impact You will design, build, and iterate on AI-powered product experiences across Fleetio’s Rails and React appli...