Senior Systems Administrator Job Chicago area,Illinois USA,IT/Tech

Who you are

7+ years of experience administering corporate IT environments in a Systems Administrator, Senior Systems Administrator, or similar role
Experience supporting macOS, Linux, and Windows endpoints at scale, including MDM, patch management, endpoint security, and device lifecycle management
Hands-on experience administering on-prem Linux servers (Ubuntu/Debian), including CLI, shell scripting, networking, hardening, and infrastructure automation/CI/CD
Experience evaluating, selecting, implementing, and administering IT platforms, rather than only operating established tooling
Strong networking experience across firewalls, switches, wireless, VPNs, and office connectivity;
Ubiquiti/Uni Fi experience strongly preferred
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 troubleshooting skills across hardware, operating systems, networking, identity, and SaaS, with a customer-first approach to employee IT support
Experience managing technology vendors and technical purchasing decisions, with the organizational skills to balance day-to-day support and longer-term infrastructure projects
Excellent written and verbal communication skills, including the ability to build trust with employees and explain technical concepts to technical and non-technical audiences

What the job involves

As our Senior Systems Administrator, you'll play a foundational role in shaping and operating Tovala's internal IT environment
You'll own the systems, tools, and processes that keep our employees productive, secure, and connected, while helping us build a scalable, modern IT function that supports a growing business
This is a highly hands-on individual contributor role for someone who enjoys solving a wide variety of technical challenges-from helping an employee troubleshoot a laptop issue to designing endpoint management standards, 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 to make thoughtful decisions about the systems and technologies that support our teams
This is a contract-to-hire opportunity
We're looking for someone who can establish the right technical foundation and operational maturity to support Tovala's long-term IT strategy, with the opportunity to transition into a full-time role as those capabilities are established
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
Evaluate, select, implement, and operate modern endpoint management, device management, endpoint detection and response (EDR/XDR), patch management, and related IT administration tools
Develop scalable processes for device provisioning, inventory management, onboarding, offboarding, lifecycle management, and hardware refreshes
Own administration of Tovala's corporate network infrastructure, including Ubiquiti switches, wireless networks, firewalls, VPN technologies, conferencing equipment, and connectivity across multiple office locations
Partner with Engineering leadership to plan network improvements, evaluate vendors, and evolve our IT infrastructure as the company grows
Own our endpoint security program, including endpoint protection, incident response, security monitoring, and remediation of endpoint-related threats
Manage Google Workspace administration, identity management, email security, and secure access to company systems
Administer our identity and access management tools and evolve our practices to improve security and employee experience
Manage relationships with IT vendors and technology partners, helping evaluate products, negotiate renewals, and ensure we're getting the most value from our investments
Create clear documentation and standard operating procedures that improve consistency and enable future growth
Partner with Engineering leadership on broader cybersecurity initiatives, infrastructure planning, and long-term IT strategy
Continuously identify opportunities to improve…