Senior Software Engineer, Actionable Intelligence

Fleetio is a modern software platform that helps organizations manage their fleet operations. They are seeking a Senior Software Engineer for their Actionable Intelligence Team to build AI-powered product experiences that enhance customer decision-making and streamline workflows.

Responsibilities:

• 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

Requirements:

• 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
• 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