Senior Software Engineer, AI Full Time

A little about us…Fleetio is a modern software platform that helps thousands of organizations around the world 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 Series D 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: https://www.youtube.com/watch?v=IlvIbwZT3oU
Our careers page: https://www.fleetio.com/careers

Job Description

• The Engineering Team at Fleetio is expanding and has an opportunity for a Senior Software Engineer to join our AI team. We are looking for a full-stack Ruby on Rails Engineer with experience building AI-enabled solutions. In this role, you will work closely with our Engineering and Product leaders to build and drive our AI roadmap.

More About Engineering
Watch our culture videos: https://fleet.io/culture
Engineering culture, interview process, and videos: https://www.fleetio.com/careers/engineering
Fleetio Go overview video: https://www.fleetio.com/go
More about the Fleetio platform: https://www.fleetio.com/features
API docs: developer.fleetio.com
Test drive Fleetio to get an even better feel for what we’re building: https://www.fleetio.com/register
This is a remote opportunity and is open to candidates in the United States, Canada, or Mexico.

Who you are

• The ideal candidate for this role is someone who loves being in the driver’s seat and exploring what’s possible. You are someone who enjoys solving problems and transforming user experience with AI-enabled solutions. You enjoy ideation, experimentation, and iteration. You effectively partner with technical and non-technical stakeholders. You are pragmatic and exercise good judgment.

Your impact

• You’ll work closely with Product Managers, Designers, and other Engineers to research, plan, design, and build features that leverage AI to make Fleetio’s users more productive.
• You’ll automate repetitive workflows while surfacing proactive insights.
• Develop prototypes and validate solutions through fast experimentation.
• Partner with product and engineering partners to ideate, design, and implement solutions.
• Analyze complex data sets to identify patterns and anomalies, aiding in the development of relevant and accurate solutions.

Your experience

• 5+ years of experience with Ruby on Rails, with expertise in backend architecture and design patterns.
• Experience with React and TypeScript, capable of contributing to full-stack solutions.
• Proven experience building and deploying successful AI-enabled solutions.
• Familiarity with AI and ML frameworks.
• Excellent written and verbal communication skills.
• Clear, intentional communication skills with a track record of thriving in a highly async environment.
• Bachelor’s or Master’s degree in computer science, mathematics, statistics, data science, or related fields.

Considered a plus

• Experience with Natural Language Processing and Computer Vision.
• Experience with cloud computing platforms like AWS, Azure, and GCP.
• Advanced knowledge in machine learning and associated algorithms (Linear regression, Logistic regression, Decision tree, Bayesian, etc.).
• Expertise in developing and deploying AI and ML models.
• Familiarity with using and configuring user monitoring and analytics tooling.
• Previous experience working on a Growth engineering team.

Tagged as: software engineering