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Systems Administrator

Remote - USA, CAN, MEX

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

  • Take ownership of configuring and managing critical SaaS applications such as Okta, Google Workspace, and others, ensuring optimal performance and user experience.
  • Help craft the scalability and vision of the IT Operations and Corporate Security functions in a rapidly scaling, tech-forward environment
  • Identify areas for improvement within the Fleetio tech stack, recommend and implement changes to enhance efficiency, security, and productivity, contributing to streamlined operations.
  • Collaborate with various teams to understand business requirements and translate them into practical SaaS configurations and solutions, fostering organizational alignment.
  • Research and evaluate new SaaS applications aligned with organizational goals, presenting recommendations for adoption.
  • Provide tier 2 support for the help desk team, assisting with complex technical issues and ensuring smooth operations, contributing to enhanced user satisfaction, along with fostering a culture of mentorship and growth amongst junior team members.
  • Stay updated with industry trends and best practices, incorporating relevant advancements into tech stack management strategies, ensuring continuous improvement, and staying ahead of the curve.

Your experience

  • Proven experience as a Systems Administrator, focusing on managing SaaS applications and configurations, including Atlassian, Github, Google Workspace, M365, Slack, Zoom, Okta.
  • Highly proficient with macOS, iOS/iPadOS and experience with Apple specific MDM systems.
  • Proficient in email security platforms, such as Proofpoint or Mimecast, for advanced threat protection and phishing prevention.
  • Skilled in SaaS Security Posture Management (SSPM) platforms like Adaptive Shield or Valence Security, ensuring robust cloud application security.
  • Experienced with network security technologies, including VPN, Secure Web Gateway (SWG), and related access controls, to safeguard corporate environments.
  • Strong proficiency in configuring and maintaining SaaS applications such as Okta, Google Workspace, and device deployment and management with MDM platforms such as Mosyle, Kandji, or JAMF.
  • Experience with automation and workflow tools, such as Okta Workflows or Zapier.
  • Familiarity with general IT security practices and protocols, with the ability to implement security measures within SaaS environments.
  • Excellent problem-solving skills and the ability to troubleshoot technical issues effectively.
  • Strong communication skills, both written and verbal, with the ability to convey technical concepts to non-technical stakeholders.
  • Proactive attitude towards identifying and implementing process improvements.
  • Ability to work collaboratively in a team environment, fostering junior members of the team while also advancing work forward independently when required.

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.

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We use AI-assisted tools to support our application review process. These tools help us assess qualifications and assist our recruiting team in identifying candidates whose skills and experience closely match the job requirements we selected for this role. If you’d prefer to opt out of profiling, you can contact us at recruiting@fleetio.com, and we’ll review your application without AI assistance.

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