Senior Software Engineer, AI

Job Description The Engineering Team at Fleetio is expanding and has an opportunity for a Senior Software Engineer to join our AI team. We are looking for a full-stack Ruby on Rails Engineer with experience building AI-enabled solutions. In this role, you will work closely with our Engineering and Product leaders to build and drive our AI roadmap. little about us… Fleetio is a modern software platform that helps thousands of organizations around the world 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 Series D 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 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. Who you are The ideal candidate for this role is someone who loves being in the driver’s seat and exploring what’s possible. You are someone who enjoys solving problems and transforming user experience with AI-enabled solutions. You enjoy ideation, experimentation, and iteration. You effectively partner with technical and non-technical stakeholders. You are pragmatic and exercise good judgment. Your impact You’ll work closely with Product Managers, Designers, and other Engineers to research, plan, design, and build features that leverage AI to make Fleetio’s users more productive. You’ll automate repetitive workflows while surfacing proactive insights. Develop prototypes and validate solutions through fast experimentation. Partner with product and engineering partners to ideate, design, and implement solutions. Analyze complex data sets to identify patterns and anomalies, aiding in the development of relevant and accurate solutions. Your experience 5+ years of experience with Ruby on Rails, with expertise in backend architecture and design patterns. Experience with React and TypeScript, capable of contributing to full-stack solutions. Proven experience building and deploying successful AI-enabled solutions. Familiarity with AI and ML frameworks. Excellent written and verbal communication skills. Clear, intentional communication skills with a track record of thriving in a highly async environment. Bachelor’s or Master’s degree in computer science, mathematics, statistics, data science, or related fields. Considered a plus Experience with Natural Language Processing and Computer Vision. Experience with cloud computing platforms like AWS, Azure, and GCP. Advanced knowledge in machine learning and associated algorithms (Linear regression, Logistic regression, Decision tree, Bayesian, etc.). Expertise in developing and deploying AI and ML models. Familiarity with using and configuring user monitoring and analytics tooling. Previous experience working on a Growth engineering team. Benefits Multiple health/dental coverage options Vision insurance Incentive stock options 401(k) match of 4% PTO - 4 weeks 12 company holidays + 2 floating holidays Parental leave- birthing parent (16 weeks paid) non-birthing (4 weeks) FSA & HSA options Short and long term disability (short term 100% paid) Community service funds Professional development funds Wellbeing fund - $150 quarterly Business expense stipend- $125 quarterly Mac laptop + new hire equipment stipend Monthly catered lunches Fully stocked kitchen with tons of drinks & snacks Remote working friendly since 2012 #LI-REMOTE Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need. This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will. If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.