Senior Systems Administrator
Tovala
Chicago, United States Posted October 9, 2026
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Salary Range
$120,000 - $140,000
Job Description
Join Tovala as a Senior Systems Administrator, where you'll play a crucial role in shaping and operating our internal IT environment. This hands-on individual contributor role involves troubleshooting technical issues, administering network infrastructure, evaluating new tools, and strengthening our security posture. You'll have significant ownership over the direction of our corporate IT environment and partner closely with Engineering leadership. This is a contract-to-hire opportunity with the potential to transition into a full-time role.
- Serve as the primary point of contact for employee IT support, resolving a wide range of hardware, software, networking, and account issues while delivering an outstanding support experience.
- Administer and maintain our corporate endpoint environment across macOS, iOS, Windows and Linux devices, ensuring systems remain secure, compliant, and up to date.
- Own administration of Tovala's corporate network infrastructure, including Ubiquiti switches, wireless networks, firewalls, VPN technologies, conferencing equipment, and connectivity across multiple office locations.
- Strong troubleshooting skills across hardware, operating systems, networking, identity, and SaaS, with a customer-first approach to employee IT support
- Excellent written and verbal communication skills, including the ability to build trust with employees and explain technical concepts to technical and non-technical audiences
- Hands-on experience administering on-prem Linux servers (Ubuntu/Debian), including CLI, shell scripting, networking, hardening, and infrastructure automation/CI/CD
- Experience supporting macOS, Linux, and Windows endpoints at scale, including MDM, patch management, endpoint security, and device lifecycle management
- 7+ years of experience administering corporate IT environments in a Systems Administrator, Senior Systems Administrator, or similar role
- Experience evaluating, selecting, implementing, and administering IT platforms, rather than only operating established tooling
- Experience administering Google Workspace or similar identity platforms, with knowledge of IAM, email security, EDR/XDR, and security best practices
- Experience responding to endpoint security incidents and partnering on broader security initiatives
- Strong networking experience across firewalls, switches, wireless, VPNs, and office connectivity; Ubiquiti/UniFi experience strongly preferred
- Experience managing technology vendors and technical purchasing decisions, with the organizational skills to balance day-to-day support and longer-term infrastructure projects
Required Skills
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