Developer Operations System Engineer Jobs in Chicago, IL

CoinFlip is a global digital currency platform company focused on providing consumers with simple and secure access to buy and sell cryptocurrency. The company operates the world's largest network of cryptocurrency kiosks by transaction volume, with more than 5,500 kiosks across 49 U.S. states, Puerto Rico, Canada, Australia, New Zealand, South Africa, Italy, Panama, Brazil, Mexico, and Spain. CoinFlip’s digital currency kiosks make buying and selling major cryptocurrencies accessible for consumers who wish to purchase digital currency using cash.

CoinFlip also operates CoinFlip Preferred, a personalized over-the-counter service that provides investors with custom, white-glove support for their cryptocurrency transactions. In 2022, CoinFlip launched CoinFlip Ventures, an investment group offering coaching, funding, and networking support to early-stage crypto and web3 projects. We also offer the CoinFlip Crypto Wallet, a self-custodial cryptocurrency wallet available for iOS and Android devices.

CoinFlip was founded in 2015 by Daniel Polotsky, Kris Dayrit, Alan Gurevich, and Ben Weiss. Headquartered in Chicago, CoinFlip placed in the top 500 on the 2021, 2022, and 2023 Inc. 5000 list, and on the 2022 and 2023 Deloitte Technology Fast 500, was named the 2021 and 2022 #1 fastest-growing company in Chicago by Crain's, ranked in Chicago Tribune’s Top Workplaces in 2021 and 2022, and was awarded the 2021 and 2022 Stevie ® Awards for Customer Service. To learn more about CoinFlip and how to get started on your digital currency journey, visit www.CoinFlip.tech.

We’re seeking a DevOps Engineer to join our growing infrastructure team. You’ll be a key driver in building, scaling, and maintaining our cloud-native, multi-region infrastructure using AWS, Kubernetes, and Terraform. You will work closely with engineering, legal, and security teams to ensure our systems meet the highest standards of compliance, security, and reliability.

This role requires a deep understanding of cloud infrastructure, automation best practices, and cross-functional collaboration in highly regulated environments.

Responsibilities:

• Build and manage AWS and EKS infrastructure via Terraform with an emphasis on scalability and maintainability.
• Manage and scale our Kubernetes (EKS) clusters for high availability and fault tolerance.
• Maintain, provision, and regularly upgrade various AWS components (RDS, EKS, etc.)
• Oversee the organization’s Gitlab infrastructure and implement high standards
• Build robust CI/CD pipelines and streamline application deployment processes
• Collaborate with security and legal teams to ensure future compliance with regulatory standards (e.g., SOC 2, GDPR).
• Monitor infrastructure health and performance using observability tools (e.g., Grafana, Wiz, CloudWatch).
• Implement automated security controls and proactive incident response mechanisms.
• Participate in architecture reviews, capacity planning, and disaster recovery strategy development.
• Provide mentorship to junior DevOps and SRE team members.
• Lead incident response and root cause analysis for infrastructure-related issues.
• Other duties as assigned.

Qualifications:

• 2+ years of hands-on experience in DevOps or Site Reliability Engineering roles.
• Expert-level experience with AWS services, especially in multi-region deployments.
• Strong proficiency in Terraform, with a track record of managing complex IaC projects.
• Deep understanding of Kubernetes architecture, associated tools (kubectl, helm, prometheus, k9s, etc.), and operational practices.
• Experience working in compliance-heavy environments and collaborating with legal and security teams.
• Proficiency in scripting languages (Python, Bash, etc.).
• Strong background in monitoring, alerting, and logging systems.
• Familiarity with container security, IAM policies, VPC design, and cloud networking.

Nice to have:

• Basic knowledge of cryptocurrency and blockchains.
• General passion and knowledge of fintech and cryptocurrency.

Why Join Us?

• Modern tech stack with opportunities to influence key architectural decisions.
• Dynamic and supportive team culture.
• Work on infrastructure challenges at scale in a multi-region environment.
• Opportunity to drive real impact in security, compliance, and reliability.

Compensation:

Annual Base Salary: $90,000 - $120,000 dependent on experience level

Working at CoinFlip means collaborating with experienced and innovative leaders who share a clear vision and a track record of success. We offer a collaborative and positive working environment where we encourage employees to balance productivity with time to recharge. Compensation is above and beyond a typical “startup” — we offer competitive salaries, performance-based incentives, and competitive benefits for full-time employees.

CoinFlip values diversity in the workplace and is an equal opportunity employer committed to providing an inclusive and accessible work environment. We thank all candidates who apply, but only those selected for an interview will be contacted.

By applying to this role, you give express consent to CoinFlip to send you informational text (SMS) messages regarding this role and the application process. You can cancel the SMS service at any time by replying "STOP" to the text message you received. If at any time you forget what keywords are supported, just reply "HELP." Message and data rates apply. If you require a special accommodation, please let us know and we’ll work with you to meet your needs.