[Hiring] Senior Software Engineer, Actionable Intelligence @Fleetio

Role 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.

• Currently working on Service Advisor .
• Exploring new AI tools 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.

• Design, build, and iterate on AI-powered product experiences across Fleetio’s Rails and React application.
• Partner closely with Product, Design, Data, Customer Success, and other engineers to identify customer problems where AI can meaningfully improve the workflow.
• Create high-quality front-end experiences using Fleetio’s current React, TypeScript, Vite, Storybook, Tailwind, and component patterns.
• Work across the stack, including Rails APIs, database-backed product workflows, AI integration points, prompts, evaluation flows, observability, and customer-facing UI.
• Prototype quickly, learn from experiments, and help the team decide when to iterate, harden, or discard an approach.
• Review code and designs with a strong eye for user experience, front-end quality, correctness, readability, performance, security, and long-term maintainability.
• Mentor other engineers in React, TypeScript, Rails, AI tooling, experimentation, and pragmatic product engineering practices.

Qualifications

• 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.
• Strong product instincts and care about whether a feature creates a clear, measurable customer outcome.

Requirements

• 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