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Fleetio · Hiring

Systems Administrator

Remote - USA, CAN, MEXRemoteFull-time

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:

Description

The IT Operations Team at Fleetio has an opportunity for a Systems Administrator to join our team. In this role, you will help improve and scale the efficiency and security of our internal IT infrastructure while creating a best-in-class experience for our employees.

You will be responsible for optimizing and maintaining the configurations of critical applications such as Okta, Google Workspace, Zoom, 1Password, etc. You will play a pivotal role in identifying areas of improvement, recommending new applications, reducing redundant tooling, and providing tier 2 and escalation support to our help desk team.

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 $144M in Series C in June of 2023 and are on an exciting trajectory as a company.

More about our team and company:

Who you are

The ideal candidate for this role should be a seasoned macOS administrator, and possesses a solid understanding of SaaS technologies. You are driven by the challenge of optimizing and maintaining IT systems to their fullest potential. Your knack for problem-solving shines through as you consistently identify areas for improvement within our tech stack and implement effective solutions to enhance efficiency and productivity. Strong communication skills enable you to bridge the gap between technical complexities and non-technical stakeholders, fostering collaboration and understanding across diverse teams. With an innate curiosity and innovative mindset, you continuously seek out new SaaS applications and technologies, seeking opportunities to improve organizational processes and drive technological advancement. Excelling in collaborative team environments, you work closely with cross-functional teams to grasp business requirements and translate them into actionable solutions that propel the organization forward. Your proactive approach to learning ensures you stay updated with the latest industry trends and best practices, allowing you to incorporate relevant advancements into your work and remain at the forefront of technology. This role is part of the IT Operations Department and will report to the Manager, IT & Security.

Your impact

Your experience

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

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.

Interested in This Role?

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