Systems Administrator

Fleetio

. Improve and scale the efficiency and security of Fleetio’s internal IT infrastructure .

Posted 11/10/2026full-timeRemote • United States, Canada, MexicoMid-LevelSeniorWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in managing and optimizing SaaS applications and configurations, with a strong focus on security and efficiency. Proficient in collaborating with teams to translate business needs into effective technology solutions while mentoring junior staff.

Highest-signal resume keywords

SaaS Application ManagementNetwork Security TechnologiesEmail Security PlatformsSaaS Security Posture ManagementMacOS and iOS/iPadOS Proficiency

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

SaaS Application ConfigurationNetwork SecurityEmail SecuritySaaS Security Posture ManagementAutomation ToolsMDM SystemsTechnical TroubleshootingProcess ImprovementConfiguration ManagementHelp Desk Support

Soft Skills

Problem-SolvingCommunicationCollaborationMentoringProactive Attitude

Tools & Technologies

OktaGoogle WorkspaceZoom1PasswordAtlassianGithubM365SlackProofpointMimecast

Industry Keywords

IT InfrastructureCorporate SecuritySaaS ApplicationsTech-Stack ImprovementsHelp Desk Support

Tech Stack

Tools & technologies

iOSJamfMacOS

About the role

Key responsibilities & impact

Improve and scale the efficiency and security of Fleetio’s internal IT infrastructure
Optimize and maintain configurations of critical SaaS applications including Okta, Google Workspace, Zoom, and 1Password
Own configuration and management of critical SaaS applications, ensuring optimal performance and user experience
Help shape the scalability and vision of IT Operations and Corporate Security
Identify and implement tech-stack improvements to enhance efficiency, security, and productivity
Collaborate with teams to translate business requirements into SaaS configurations and solutions
Research and evaluate new SaaS applications and present adoption recommendations
Provide tier 2 and escalation support for complex help desk issues
Mentor junior team members
Monitor industry trends and incorporate relevant advancements into technology management strategies

Requirements

What you’ll need

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
Experienced with network security technologies, including VPN, Secure Web Gateway (SWG), and related access controls
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
Excellent problem-solving skills and ability to troubleshoot technical issues effectively
Strong written and verbal communication skills, including conveying technical concepts to non-technical stakeholders
Proactive attitude toward identifying and implementing process improvements
Ability to collaborate in a team environment, foster junior team members, and advance work independently

Benefits

Comp & perks

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