Operating System Engineer Jobs in Chicago, IL (NOW HIRING)

About Grubhub

At Grubhub, we believe food is more than just a meal: It’s a source of discovery, connection, and pure enjoyment. There’s a time and place for every type of dish, from hidden neighborhood gems to tried-and-true favorites, and we exist to connect people with the food they love in all the ways they like to dig in. We’ve been at it since 2004, but now, as part of Wonder, Grubhub is operating with a renewed sense of momentum and the high-velocity energy of a powerhouse startup.

As a leading U.S. ordering and delivery marketplace, we feature over 415,000 merchants in more than 4,000 cities, creating the ultimate food experience by elevating online ordering through innovative restaurant technology, easy-to-use platforms, and an improved delivery experience. We are constantly finding new ways to innovate—from integrated grocery delivery with groceries powered by Instacart to exclusive loyalty programs. Join our team, based out of New York City, Chicago and Denver, and help us give our diners the exceptional value they deserve.

About The Opportunity 

As a Senior Engineer on the Runtime Automation team, you will design, automate, and secure our core infrastructure, deployment platforms, and CI/CD ecosystems. Our team is responsible for managing our centralized Enterprise Logging Platform (Vector, Datadog, Splunk), engineering robust multi-cloud solutions across AWS and GCP, and driving automated deployment infrastructure via Jenkins and Spinnaker. In this role, you will focus deeply on containerization (Docker), Infrastructure as Code (IaC via Terraform and/or Pulumi), server image management (AMI), and low-level Linux operating system engineering, while ensuring top-tier observability and strict security across our mission-critical card payment environment. This is a high-impact position driving continuous reliability, deep system optimization, and automation across our entire technology ecosystem.

The Impact You Will Make

• Guide Technical Direction and Innovation: help define architectural strategies, introducing modern platform engineering practices, and driving complex technical decisions across infrastructure and CI/CD platforms.

• Coach and Mentor Engineers: Foster a culture of technical excellence by mentoring and coaching mid-level and junior engineers, conducting rigorous code and architecture reviews, and promoting continuous knowledge sharing.

• Scale Infrastructure as Code (IaC): Architect, maintain, and modernize declarative infrastructure across cloud environments using Terraform and/or Pulumi to drive reliability and self-service capabilities.

• Orchestrate Global CI/CD Infrastructure: Own, scale, and optimize high-throughput multi-cloud deployment pipelines using Jenkins and Spinnaker, ensuring fast, secure, and friction-free software delivery workflows.

• Secure and Standardize Payment Environments: Architect and harden our card payment infrastructure, ensuring the highest standards of data security, compliance, and proactive vulnerability mitigation.

• Optimize Infrastructure and Container Lifecycles: Own and scale the automated pipeline for AWS AMIs and Docker containers, using configuration management tools to ensure consistent, secure, and reliable image deployment workflows.

• Optimize Systems: Troubleshoot and optimize mission-critical infrastructure at scale, leveraging deep Linux internals knowledge and kernel-level tuning to maximize efficiency and stability.

• Advance Enterprise Logging and Observability: Scale and maintain our data ingestion workflows and centralized logging platform using Vector, Datadog, and Splunk, building robust dashboards and advanced alerting mechanisms to minimize downtime.

• Foster Operational Excellence: Participate in the team’s on-call rotation as an incident responder, leading postmortem discussions and writing automation scripts to eliminate repetitive operational toil.

What You Bring to the Table

• Technical Leadership and Mentorship: Proven experience or strong aptitude for helping guide technical direction, making sound architectural choices, and successfully coaching/mentoring other engineers.

• Infrastructure as Code (IaC) Expertise: Hands-on familiarity and engineering experience with modern IaC frameworks, specifically Terraform and/or Pulumi, to manage complex cloud resources.

• CI/CD and Deployment Expertise: Robust, hands-on familiarity with configuring, scaling, and troubleshooting enterprise CI/CD systems, specifically Jenkins pipelines and Spinnaker deployments.

• Linux Internals and Systems Engineering: Deep, expert-level proficiency in Linux operating systems with proven experience in low-level system performance troubleshooting.

• Automation and Advanced Scripting: High proficiency in scripting and software automation utilizing Python and Bash to build internal tools, optimize processes, and eliminate technical overhead.

• Core Cloud Expertise: Strong engineering experience with AWS services (specifically EC2, Load Balancers, and AMI building) along with robust operational familiarity with Google Cloud Platform (GCP).

• Containerization and Image Automation: Advanced, hands-on experience with Docker containerization and automated configuration management tools (such as Ansible).

• Observability and Logging Expertise: Solid command over administering, configuring, and scaling large-scale enterprise logging and monitoring solutions, specifically Vector, Datadog, and Splunk.

• Security-First Mindset: Strong familiarity with building and maintaining secure infrastructure, particularly within highly regulated or card payment environments.

• Collaboration and Communication: Excellent problem-solving skills, rigorous attention to detail, and a proven ability to lead cross-functional incident responses and knowledge sharing.

• Nice-to-Have / Plus: Prior exposure to or experience with Kubernetes-native orchestration and architectures (e.g., EKS, GKE).

Our hybrid model requires 3 days a week in the office. That said, many team members choose to come in more often to take advantage of in-person collaboration and connection. You're welcome—and encouraged—to be in the office up to 5 days a week if it works for you. 

#LI-Hybrid

Illinois: $158,500 - $172,000 per year.

New York: $176,000 - $191,000 per year.

Wonder uses geographic-specific salary structures, which means the salary offered may vary depending on where the job is located. The final salary offer will take into account various factors, such as the candidate's skills, education, training, credentials, and experience.

Benefits

The benefits applicable to this role include a competitive compensation package with equity and a 401(k). We also offer a choice of medical, dental, and vision plans, company paid short and long term disability coverage, paid time off including flexible time off for exempt employees, paid vacation for non-exempt employees, and paid sick leave in compliance with applicable law in addition to paid parental leave, discounted meals and exclusive perks across the Wonder family of brands.

Eligibility, effective dates, and available plan options vary by employment classification and location. To learn more about benefits for this role, visit our Careers page here.  

A Final Note

At Wonder, we build the best teams by hiring with an objective lens — evaluating people for their potential while championing diversity, equity, and inclusion. We do not discriminate based on race, color, religion, gender identity or expression, sexual orientation, national origin, age, military service eligibility, veteran status, marital status, disability, or any other protected class. As part of our commitment to fair and compliant hiring practices, Wonder participates in the federal government's E-Verify program to confirm employment eligibility. If you need an accommodation during the interview process, please let your recruiter know.

We look forward to hearing from you! We'll contact you via email or text to schedule interviews and share information about your candidacy.