Senior Software Engineer, Actionable Intelligence

Fleetio

3d•Remote

About The Position

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. 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.

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.

Nice To Haves

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

Responsibilities

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, while caring deeply about accessibility, usability, maintainability, and performance.
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.

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