Senior Software Engineer, Actionable Intelligence at Fleetio

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: [Upgrade to PRO to see link] • Our careers page: [Upgrade to PRO to see link] 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: [Upgrade to PRO to see link] • Engineering culture, interview process and videos: [Upgrade to PRO to see link] • Fleetio overview video: [Upgrade to PRO to see link] • Fleetio Go overview video: [Upgrade to PRO to see link] • More about the Fleetio platform: [Upgrade to PRO to see link] • API docs: developer.fleetio.com • Test drive Fleetio to get an even better feel for what we're building: [Upgrade to PRO to see link] 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 application. • You will partner closely with Product, Design, Data, Customer Success, and other engineers to identify customer problems where AI can meaningfully improve the workflow. • You will create high-quality front-end experiences using Fleetio’s current React, TypeScript, Vite, Storybook, Tailwind, and component patterns, while caring deeply about accessibility, usability, maintainability, and performance. • You will work across the stack, including Rails APIs, database-backed product workflows, AI integration points, prompts, evaluation flows, observability, and customer-facing UI. • You will prototype quickly, learn from experiments, and help the team decide when to iterate, harden, or discard an approach. • You will review code and designs with a strong eye for user experience, front-end quality, correctness, readability, performance, security, and long-term maintainability. • You will mentor other engineers in React, TypeScript, Rails, AI tooling, experimentation, and pragmatic product engineering practices. Your experience • 5+ years experience with Ruby on Rails • 5+ years experience with ReactJS, Typescript • High comfort level with HTML & CSS and ability to create dynamic UX workflows and custom-designed UI components. • Strong understanding of object-oriented programming and relational databases, such as PostgreSQL. • You have strong product instincts and care about whether a feature creates a clear, measurable customer outcome. Nice to have • Experience building AI-powered product features using LLM APIs, prompt engineering, tool/function calling, retrieval, evaluations, or human-in-the-loop workflows. • Experience with observability, feature flags, gradual rollouts, A/B tests, or product experimentation. • Project experience with TailwindCSS Benefits • Multiple health/dental coverage options (100% coverage for employee, 50% for family) • Vision insurance • Incentive stock options • 401(k) match of 4% • PTO - 4 weeks (increases at year two!) • 12 company holidays + 2 floating holidays • Parental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid) • 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 • Fully stocked kitchen with tons of drinks & snacks (BHM only) • 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.