Systems Administrator - Fleetio

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!

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.

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. 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.
• Collaborate with various teams to understand business requirements and translate them into practical SaaS configurations and solutions.
• 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 mentoring junior team members.
• Stay updated with industry trends and best practices, incorporating relevant advancements into tech stack management strategies.

Your experience

• Proven experience as a Systems Administrator, focusing on managing SaaS applications and configurations (Atlassian, Github, Google Workspace, M365, Slack, Zoom, Okta).
• Highly proficient with macOS, iOS/iPadOS, and experience with Apple-specific MDM systems (Mosyle, Kandji, JAMF).
• Proficient in email security platforms (Proofpoint or Mimecast).
• Skilled in SaaS Security Posture Management (SSPM) platforms like Adaptive Shield or Valence Security.
• Experienced with network security technologies, including VPN, Secure Web Gateway (SWG), and related access controls.
• Experience with automation and workflow tools, such as Okta Workflows or Zapier.
• Familiarity with general IT security practices and protocols.
• Excellent problem-solving and communication skills.