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Senior Software Engineer, AI & Data

Remote - USA, CAN, MEX

Description

Fleetio is looking for a product-minded and team-oriented Senior Software Engineer experienced with data-driven AI experimentation to join our Product Engineering team. This is an opportunity to shape our AI strategy and build AI-powered features that will transform how fleets operate. You will partner closely with engineering and product leaders, contributing to Fleetio’s roadmap and influencing the direction of our AI investments.

As a founding member of our AI Engineering team, you will be responsible for implementing new features and enabling the wider Fleetio Product Engineering team's adoption of AI best practices and experimentation. 

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

This is a remote opportunity and is open to candidates in the United States, Canada, or Mexico.

Who You Are

Our ideal candidate for this role has a passion for and experience collaborating with others and transforming user experience with AI-enabled solutions. You have strong, loosely held opinions, are a proactive problem-solver, a data-driven decision maker, and thrive in a fast-paced environment. You have extensive experience planning, designing, and iterating on end-to-end product features with cross-functional team members and executive leaders. Your ability to foster adoption and communicate effectively with technical and non-technical team members is key to your success. This role is a part of the Product Engineering department, and you will report directly to the Chief Technology Officer. 

Your Impact

  • You will participate in planning, designing, and implementing AI-driven features to increase product and feature adoption. 
  • As a subject matter expert, advise executives and team members on technology, strategy, and policy issues associated with AI
  • Develop and train ML models and optimize AI algorithms.
  • 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 to aid in developing relevant and accurate solutions.
  • Help build data pipelines and cleanse data as necessary to train ML models.
  • Document AI processes, models, and other relevant areas as necessary.
  • Make hiring recommendations as necessary to grow and maintain relevant AI skills.

Your Experience

  • 7+ years experience as a software engineer
  • 3+ years experience with Ruby on Rails and Python
  • 2+ years building and deploying successful AI-enabled solutions
  • Ability to test and validate models
  • Familiarity with AI and ML frameworks
  • Knowledge in machine learning and associated algorithms (Linear regression, Logistic regression, Decision tree, Bayesian, etc.)
  • Excellent written and verbal communication skills
  • Bachelor’s or Master’s degree in computer science, mathematics, statistics, data science, or related fields
  • Be sure to mention "coffee" in your application so we know you actually read this

Considered a plus

  • Experience with Natural Language Processing and AI agents
  • Experience with cloud computing platforms like AWS, Azure, and GCP
  • Experience with React

Benefits

  • Multiple health/dental coverage options
  • Vision insurance
  • Incentive stock options
  • 401(k) match of 4%
  • PTO - 4 weeks
  • 12 company holidays + 2 floating holidays
  • Parental leave- birthing parent (16 weeks paid) non-birthing (4 weeks)
  • 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
  • Monthly catered lunches
  • Fully stocked kitchen with tons of drinks & snacks
  • Remote working friendly since 2012 #LI-REMOTE

Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.

This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.

If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.

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