Senior Systems Administrator

Go Fractional; Chicago (IL); Híbrido; USD 120.000 - 140.000; A tiempo parcial

Descripción de la vacante

Tovala is seeking a Senior Systems Administrator to shape and operate our internal IT environment from Chicago. You’ll own systems, tools, and processes that keep employees productive, secure, and connected while building a scalable IT function and supporting growth.

This hands-on role covers endpoint management, network infrastructure, security, and tool evaluations. You’ll partner with Engineering leadership on IT strategy and help evolve our security posture and operational maturity.

Formación

• 7+ years of experience administering corporate IT environments in senior roles.
• Experience supporting macOS, Linux, and Windows endpoints at scale, including MDM, patch management, endpoint security, and device lifecycle management.
• Hands-on administration of on-prem Linux servers (Ubuntu/Debian) via CLI, scripting, networking, hardening, and automation/CI/CD.
• Experience evaluating, selecting, implementing, and administering IT platforms, not just operating established tooling.
• Strong networking experience across firewalls, switches, wireless, VPNs; UniFi experience preferred.
• Experience administering Google Workspace; knowledge of IAM, email security, EDR/XDR, and security best practices.
• Experience responding to endpoint security incidents and partnering on security initiatives.
• Strong troubleshooting across hardware, OS, networking, identity, and SaaS with a customer-first IT support approach.
• Experience vendor management and technical purchasing decisions; balancing day-to-day support with long-term projects.
• Excellent written and verbal communication; ability to explain technical concepts to diverse audiences.

Responsabilidades

• Own and operate the company’s internal IT environment, shaping scalable IT processes.
• Be the hands-on lead for endpoint management, network infrastructure, and security posture across multiple OSs.
• Drive tool selection, deployment, and maintenance for CI/CD and IT administration.
• Develop provisioning, onboarding/offboarding, asset lifecycle, and hardware refresh processes.
• Manage corporate network infrastructure including Ubiquiti gear, firewalls, VPNs, and multi-site connectivity.
• Collaborate with Engineering leadership on IT strategy, security initiatives, and vendor evaluations.
• Maintain and improve incident response, security monitoring, and endpoint protection programs.
• Own Google Workspace administration, IAM, email security, and secure access strategy.

Conocimientos

Senior IT experience

macOS

Linux

Windows

MDM

Patch management

Endpoint security

CI/CD

Networking

Google Workspace administration

IAM

EDR/XDR

Security incident response

Vendor management

Documentation

Herramientas

Ubiquiti UniFi

CI/CD pipelines

Endpoint protection tools

EDR/XDR tools

Descripción del empleo

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/UniFi 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 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

Compensation: $120-140k + Equity

Location: Chicago (Office located in W Adams St, Chicago)

Level: Senior and Expert level

Employment Type: Contract-to-hire