Senior DevOps Engineer Chicago, IL | Hybrid-Remote Casechek is on a mission to innovate the implant supply chain and bring greater transparency to the cost of patient care. From procurement to payment, Casechek automates workflows for vendor supported surgical procedures. Our emergent Bill Only Solution provides a comprehensive system of record for Hospitals and Health Systems to manage the complexity of surgical cases with implantable medical devices, expose hidden expenses and surface revenue opportunities. We are looking for a Senior DevOps Engineer to take ownership of our cloud infrastructure strategy and optimize security and delivery across production, staging, and development environments. In this role you will architect, build, and maintain stable and efficient cloud infrastructure through automation and best practices. You will collaborate with Casechek's Engineering and Security teams to monitor, troubleshoot, and continuously improve our devops practice. Casechek is a highly collaborative environment, but our team is also self-motivated and works independently. We strongly believe that great ideas are not created in isolation! Our team interacts with our healthcare customers to understand their needs and ultimately deliver the best user experience as possible. About You Passionate about automation and simplification in the cloud. Infrastructure as code is your mantra. Extensive public cloud experience (preferably AWS). High level of motivation and sense of urgency. Self-organized and meticulous. Educated in industry best practices. Focused on productivity. Responsibilities Design and troubleshoot SaaS application deployment procedures. Drive automation and best practices in our cloud infrastructure. Analyze, troubleshoot, and support infrastructure in AWS. Monitor system performance and recommend corrective action. Document current environment and ongoing maintenance of documentation. Requirements 7+ years of professional experience implementing and architecting cloud solutions infrastructure: developing CI/CD pipelines, serverless architecture patterns, monitoring system performance. Experience with GitHub Actions and AWS services (or similar platform). Proficiency with automating infrastructure and improving build times. Experience with iOS/Android mobile application build pipelines. Infrastructure as code and scripting proficiency. Experience securing infrastructure to meet HIPAA standards (preferred). Experience supporting a SOC 2 Type II certified infrastructure (preferred). Bachelor's degree or greater in computer science, engineering, or a similar field of study. Our DevOps Tech Stack AWS Terraform GitHub Actions Python Why You'll Love Working Here Competitive Salary and Annual Bonus - The salary range for this role is $130,000-$150,000 base. Opportunity for Long-Term Incentives (LTI) - Be part of our success with equity or long-term incentive plans that grow with the company. 401(k) Match - Invest in your future with our generous matching program to help you build long-term financial security. Work-from-Home Flexibility - Enjoy the freedom to work where you're most productive with a supportive hybrid (Chicago) or remote setup (National). Flexible Time Off (Unlimited PTO) - Recharge and focus on what matters most with unlimited paid time off tailored to your needs. Parental Leave - Take time to bond and care for your growing family with fully paid parental leave options. Comprehensive Medical and Dental Benefits - Prioritize your health and well-being with premium plans for you and your family. Brand-New Pro-Level Laptop - Equipped with top-tier tools and technology to set you up for success from day one. Annual Education Budget - Expand your skills and knowledge with dedicated funding for courses, certifications, and learning resources.