Senior Software Engineer, Actionable Intelligence

Overview

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:
• Our careers page:

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.

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.

• 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, Type Script, 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, Type Script, Rails, AI tooling, experimentation, and pragmatic product engineering practices.

• 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 Tailwind CSS

• Multiple health/dental coverage options (100% coverage for employee, 50% for family)
• Vision insurance
• Incentive stock options
• 4…