Senior Devops Engineer Jobs in Chicago, IL (NOW HIRING)

Jitsu gives companies of any size the power to deliver their products directly to customers' doorsteps within a day, without the typical cost and complexity of expedited shipping. Our proprietary technology provides same-day and next-day delivery to some of the world's fastest-growing brands by matching driver supply with shipper demand. Jitsu's services are live in 30 major metropolitan areas, with many more on the way.

We're looking for a Senior DevOps / Platform Engineer to help evolve the infrastructure that powers our platform, along with the tools and systems that keep our engineering team productive and shipping continuously. This is an opportunity to take an already high-performing system and team and help get them to the next level.

The ideal candidate brings deep experience in continuous integration and delivery and in cloud infrastructure and operations — ideally on Google Cloud Platform — with a demonstrated record of tackling increasingly challenging projects. You've built highly available infrastructure and efficient release processes, and you'll be a key technical leader enabling the growth of Jitsu's proprietary logistics platform, with substantial room to shape it in your own vision.

• Own key parts of the DevOps effort for a global engineering team and a platform supporting millions of transactions per day — and more than doubling annually
• Drive improvement across our development process and tooling: source control, build, test, packaging, release, and deployment
• Drive improvement in our infrastructure configuration, management, and cost efficiency
• Drive enhancement of monitoring and observability across all infrastructure and services, for both availability and performance
• Partner with other technical leaders to improve our architecture's maintainability, scalability, and resilience
• Serve as a technical lead to software and DevOps engineers on development and operations practices
• Partner with other technical leaders to strengthen our information security posture
• Contribute to the team's development and operations standards and processes

• CI/CD & release automation: Deep experience designing automated pipelines end to end — git-based source control and branching strategies, build and test automation (Jenkins, GitHub Actions, or similar), artifact and dependency management, and progressive, low-risk deployment patterns.
• Infrastructure as Code: Strong, hands-on experience with Terraform (or similar) — reusable modules, state management, and managing multi-environment infrastructure (staging, beta, production) as code.
• GitOps: Experience operating a GitOps workflow with ArgoCD (or similar) as the source of truth for declarative, auditable deployments.
• Cloud infrastructure (GCP preferred): Strong experience building and operating cloud infrastructure at scale — compute, VPC networking, storage, message queues, serverless, DNS, load balancing, IAM, and logging.
• Kubernetes operations: Production experience running and operating Kubernetes at scale — cluster lifecycle and upgrades, workload scheduling and resource management, autoscaling (HPA/cluster/event-driven), networking and ingress, and diagnosing complex cluster issues.
• Helm: Authoring, configuring, and maintaining Helm charts for templated, repeatable application deployments across environments.
• Databases at scale: Experience deploying, operating, and tuning a mix of data stores — relational (PostgreSQL / CloudSQL), NoSQL document (MongoDB), wide-column (Cassandra), and cache (Redis) — including replication, backups, scaling, and performance troubleshooting.
• Reliability & monitoring: Demonstrated track record deploying and monitoring large-scale, mission-critical services — defining SLIs/SLOs, building actionable alerting, and driving incident response and blameless post-mortems.
• Security: Solid grounding in cloud and infrastructure security — IAM, secrets management, network policy, and supply-chain hygiene.
• Bonus: Java application release engineering.

• Great communication and documentation skills
• An obsession with automation and a desire to leave things better than you found them
• A customer-first mindset and strong attention to detail
• 5+ years as a DevOps or Site Reliability Engineer
• Bonus: A sense of humor

Our core need is a strong senior DevOps / platform engineer. On top of that, it would be great to find someone curious about applying AI to operations work:

• AI-driven SRE & DevOps mindset — familiarity with AIOps (anomaly detection, intelligent alerting, predictive scaling, automated remediation) and comfort applying AI/LLMs to simplify how we operate infrastructure, pipelines, and Kubernetes.
• Building AI agents and automation that reduce operational toil — incident triage, runbook automation, log/RCA summarization, and AI-assisted CI/CD that moves us faster and toward self-healing infrastructure.

• Be part of a well-funded, fast-growing company tackling complex, relevant challenges in sustainable last-mile delivery
• Competitive compensation and equity incentives
• Health, vision, and dental insurance
• 401(k) plan
• Flexible time off

Compensation: The targeted base salary range for this role is listed in the compensation section below. Actual salary may be above or below this range based on location, skills, and relevant experience. In addition, this position may include additional compensation in the form of bonuses, equity, or commissions.

California CPRA Policy: For California residents, please see our CPRA policy regarding our data collection practices: https://www.gojitsu.com/cpra-policy-work

The pay range for this role is:

120,000 - 147,000 USD per year (United States)