Senior Systems Administrator

Tovala; Chicago (IL); On-site; USD 100,000 - 150,000; Full time

Job summary

Tovala is seeking a Senior Systems Administrator to own and operate our corporate IT environment across macOS, iOS, Windows, and Linux. The role is hands-on and highly collaborative with Engineering to mature IT systems for a growing business.

The position is contract-to-hire, with potential to become full-time as our technical foundation and operations mature, supporting employee productivity, security, and scalable IT processes across multiple office locations.

Qualifications

• 7+ years of experience administering corporate IT environments.
• Strong troubleshooting across hardware, OS, networking, identity, and SaaS.
• Hands-on Linux servers (Ubuntu/Debian) with CLI and scripting.
• Experience supporting macOS, Linux, and Windows endpoints at scale.
• Experience administering Google Workspace and IAM.
• Experience with endpoint security (EDR/XDR) and security best practices.
• Vendor management and technical purchasing experience.
• Strong communication and cross-functional collaboration abilities.

Responsibilities

• Own and run the corporate IT environment, ensuring security and reliability.
• Design and implement endpoint management standards and device provisioning processes.
• Administer network infrastructure, VPNs, firewalls, and Ubiquiti hardware.
• Manage Google Workspace, IAM, and secure access to systems.
• Lead security initiatives including EDR/XDR and incident response.
• Maintain CI/CD pipelines for internal tooling deployments.
• Evaluate and select IT platforms, tools, and vendors.
• Create clear SOPs and documentation to support growth.

Skills

Troubleshooting

Customer focus

Linux admin

Endpoint management

Google Workspace

IAM

EDR/XDR

Networking

Vendor management

MDM

Tools

Ubiquiti UniFi

VPNs

Firewalls

CI/CD

Patch management

Job description

• 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 reliability, security, automation, and the overall employee technology experience
• Administer and maintain on‑premises Linux servers — provisioning, patching, hardening, monitoring, backups, and troubleshooting — to keep internal infrastructure reliable and secure
• Maintain and improve CI/CD pipelines used to deploy and manage internal systems, automating builds, testing, and releases to increase reliability and reduce manual work

Qualifications

• 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