Sr. Systems Administrator

Tovala • Chicago, IL

2d

About The Position

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.

Requirements

• 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.

Responsibilities

• 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.

Benefits

• Flexible paid time off (with a minimum of 15 days off you HAVE to take)
• Comprehensive healthcare coverage
• 401k with match
• Free Tovala Smart Oven and discounted Tovala meals
• Paid holidays and our winter holiday office shutdown where the offices and facilities close for a week around Christmas and New Years
• Various other perks - recognition programs, continued learning stipend, casual dress code, in-office coffee, snacks and drinks, and Tovala swag

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed