Sr. DevOps Engineer

This critical hybrid role leads the end-to-end modernization of a legacy Ruby on Rails application running on AWS - migrating it into a secure, containerized, cloud-native environment while upholding the highest standards of reliability and compliance in a regulated healthcare space. The ideal candidate bridges the gap between senior application development and infrastructure engineering: someone who can reverse-engineer legacy code, architect the containerization path forward, and own the DevOps pipelines that get it there.

Core Responsibilities

Infrastructure Modernization & DevOps

• Lead the migration of legacy Ruby on Rails applications to containerized solutions (Docker/ECS), optimizing for scalability, high availability, and performance.
• Design and maintain CI/CD pipelines (Jenkins), Infrastructure as Code (Terraform, CloudFormation, Ansible), and comprehensive monitoring and alerting suites.
• Enhance deployment practices, incident response protocols, and system access logging.
• Maintain optimal cloud resource utilization by right-sizing instances, investigating overspend, and proposing actionable cost-saving recommendations.
• Set up, provision, and monitor disaster recovery regions in AWS, including multi-region database deployments.
• Support healthcare data interchange initiatives using BOOMI atoms and molecules.
• Participate in technical requirements gathering, AWS infrastructure design, and DevOps/CI/CD process design in collaboration with architecture leadership.

Application Development & Code Modernization

• Conduct deep code archeology and reverse engineering of the existing Ruby/RoR codebase to identify legacy dependencies, refactor as necessary, and facilitate containerization and CI/CD automation.
• Contribute development expertise to support application performance improvements, feature enhancements, and technical debt reduction.

Security & Compliance

• Act as a guardian of AWS infrastructure - manage CVEs, patch windows, and maintain strict HIPAA/HITRUST compliance controls.
• Oversee and maintain application and infrastructure security, including managing patch windows, vulnerability assessments, and security standards compliance.
• Adhere to all Corporate Compliance guidelines, OIG, government healthcare regulations, and privacy and security standards, including HIPAA requirements.
• Treat Protected Health Information (PHI) with the strictest confidentiality in accordance with HIPAA standards.

Operational Leadership

• Collaborate with the Managed Service Provider (MSP), ensuring a productive, aligned, and effective partnership.
• Mentor less experienced team members, promoting a culture of learning, ownership, and engineering excellence.
• Identify, analyze, and resolve system problems proactively and with urgency.

DevOps, AWS, Linux, Ruby on Rails, containerization, Linux/Unix Systems: 5+ years of hands-on Linux/Unix system administration - this is a core competency for this role.

• Strong shell scripting skills (Bash, and/or Python/Ruby for automation) are required, as is comfort diagnosing and resolving complex system-level issues under pressure.
• Experience with package management, log analysis, performance tuning, and hardening Linux systems in a regulated or security-conscious environment is expected.
• AWS Infrastructure & Containerization: 5+ years of DevOps and/or systems administration experience with deep, hands-on knowledge of EC2, ECS, ECR, RDS (Postgres), Lambda, and multi-account networking - including Docker-based container orchestration.
• Ruby on Rails Development: 5+ years of development background in Ruby/RoR - required to reverse engineer legacy code, identify dependencies, and facilitate successful containerization. Along with Linux/Unix proficiency, this is a core competency for this role.

• CI/CD: Proven experience with continuous integration tools, with a strong preference for GitHub Action expertise. Infrastructure as Code: Mastery of IaC and configuration management via Terraform, CloudFormation, Fargate, Chef and/or comparable tools.

• Security: Strong background in managing vulnerabilities, patching schedules, and operating within highly regulated frameworks (HIPAA/HITRUST).
• Database: Knowledge of database management with light DBA skills; Postgres and MySQL experience preferred.
• AI-Assisted Development: Experience working with agentic coding tools (Claude Code, Cursor, or similar) as a core part of the development workflow is a strong plus.
• AWS certification (Solutions Architect, SysOps Admin Associate, or DevOps Engineer Professional) strongly preferred.

Soft Skills & Professional Attributes

• Leadership & Ownership: Takes charge of modernization initiatives, drives them to completion within agreed timelines, and holds themselves accountable for outcomes.
• Communication: Communicates effectively across the organization - expresses ideas and project status with clarity and brevity written and verbally. Asks sharp questions, listens actively, and keeps stakeholders informed without being prompted.
• Continued Learning: Proactively stays current with emerging technologies, AI tooling, and modern deployment methodologies.
• Execution: Strong time management, attention to detail, and analytical mindset; passionate about clean code and modern infrastructure practices.
• Culture: Self-starter, motivated, and results-driven - brings positive energy, initiative, and a collaborative spirit to every engagement.