About the Role 

We are seeking a skilled and pragmatic DevOps Engineer to help manage and evolve the core infrastructure behind our production and staging environments. The majority of your work will focus on AWS and Kubernetes, with close collaboration across infrastructure, CI/CD systems, observability tooling, and core services. 

This is a highly visible individual contributor role, working directly with our CTO and Founding Partner—both of whom are deeply technical and hands-on. You’ll support a growing development team and help shape our platform’s reliability, scalability, and deployment architecture in a fast-paced, performance-driven environment. 

You’ll also be expected to comfortably engage with our Java-based applications. While this is not a pure development role, familiarity with Java is important to support production services and collaborate effectively with developers. 

Key Responsibilities 

● Operate and maintain AWS cloud infrastructure, including EC2, VPC, IAM, load balancing, networking, and secrets management. 

● Manage and optimize Kubernetes (EKS) clusters and workloads across staging and production. 

● Work with developers to support and troubleshoot Java-based services (e.g., Spring Boot), including interpreting logs, tuning performance, and debugging runtime issues.

● Build and improve CI/CD pipelines using Jenkins and Docker BuildKit.

● Support a multi-team migration from AWS Elastic Beanstalk to Kubernetes.

● Monitor system health and lead incident response using tools like Datadog.

● Support and maintain production databases, including Aurora MySQL and Redshift. 

Qualifications 

Required Skills and Experience: 

● 5–7 years of combined experience in DevOps/Software Development 

● Production experience with AWS core services (EC2, IAM, VPC, Load Balancers, Secrets Manager, etc.). 

● Hands-on experience with Kubernetes clusters and deploying containerized applications. 

● Experience working with Java-based services, with the ability to read, debug, and assist in supporting Java applications (e.g., Spring Boot). 

● Experience building and maintaining Jenkins-based CI/CD pipelines.

● Experience managing MySQL/Aurora MySQL databases in production.

● Familiarity with observability and alerting tools, such as Datadog. 

Preferred Skills: 

● Experience with EKS (Amazon Elastic Kubernetes Service). 

● Infrastructure as Code using Terraform. 

● Exposure to Cloudflare (DNS, WAF, caching, reverse proxy configurations).

● Familiarity with Redshift or other OLAP databases.

● Understanding of JVM performance tuning and profiling. 

Work Environment 

● This role requires availability during Chicago business hours. 

● Candidates may work remotely or on-site, with preference for those open to periodic in-person collaboration. 

● Participation in an on-call rotation for production systems is required. 

● The role reports to the Head of Infrastructure and Data, and involves close collaboration with the CTO and development team. 

Company Context 

We operate in the ticketing industry, where traffic patterns are highly dynamic — from sudden surges during major on-sales to quieter off-peak periods. Our infrastructure must be highly elastic, resilient, and cost-efficient. Designing for that level of performance and flexibility is not just an optimization—it’s essential to our business. This role will be instrumental in shaping and supporting that architecture as we scale and evolve our platform.