Jobs › Tovala

Sr. Systems Administrator

Tovala · Chicago, IL · $120,000–$140,000 a year · Full time · Engineering

Posted Sep 21, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

This is contract to hire. How do you feel about that?

What they are checking: The posting states it plainly, so it is asked plainly.

How do you write documentation people will actually use?

What they are checking: The posting names clear documentation and standard operating procedures to enable future growth.

What would you do

An employee cannot work and you are mid-way through a project. How do you handle that?

What they are checking: The posting has them as the primary support contact and the person building the function.

How do you decide whether to buy a tool or build a process around what you have?

What they are checking: The posting names evaluating, selecting and implementing tools, at a company still forming its IT function.

About the work

Tell me about managing endpoints across macOS, Windows and Linux.

What they are checking: The posting names all three plus iOS, and most administrators are strong in one.

Walk me through how you would build a device provisioning and offboarding process from scratch.

What they are checking: The posting names building scalable processes for provisioning, onboarding, offboarding and lifecycle.

Tell me about running an endpoint detection and response tool. What did you actually catch?

What they are checking: The posting names EDR and XDR, and owning the endpoint security programme.

Walk me through your part in a security incident.

What they are checking: The posting names incident response, monitoring and remediation as theirs to own.

Tell me about administering network infrastructure, including Ubiquiti gear and VPN.

What they are checking: The posting names Ubiquiti switches, wireless, firewalls and VPN specifically.

How do you administer Google Workspace and identity so it is secure without annoying everyone?

What they are checking: The posting names Google Workspace, identity management and improving both security and employee experience.

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The full job description

As published by Tovala.

We’re Tovala, a food-tech company reinventing home cooking to save consumers time. Through an innovative combination of hardware, software, and fresh food delivery, we make it incredibly simple for anyone to prepare and enjoy delicious, home-cooked meals without sacrificing time to do whatever matters to them. Through our superior technology, product experience and food quality, we have separated Tovala from the busy pack of other meal delivery businesses. In the process, we’ve amassed a loyal, rapidly growing following and our retention, product engagement and customer NPS are all best-in-class. We’ve raised over $100mm from great investors like Left Lane Capital, Origin Ventures, Y Combinator and Comcast Ventures and have invested strongly in building a unique culture that fosters growth, personal development and camaraderie. Position Summary 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. How you will spend your time at Tovala: • 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. About You • 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. The values we hold dear • Put the Team First - we operate with resolve and humility to do what’s best for the broader team • Get S#!t Done (Well)- We celebrate all employees for delivering high-impact work • Connect the Dots - We engage with curiosity to learn how our work impacts others at the company • Be Direct - We share our perspective openly and directly, even when it’s difficult • Embrace the Obstacles - We rise to meet challenges with a sense of urgency, resolve, and optimism • Champion the Customer - We prioritize our customer in all of our decisions At Tovala we‘re committed to building a workplace that represents a variety of backgrounds, skills, and perspectives and do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here!

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