Independent Contractor Reverse Engineering Jobs in Chicago, IL

Optum is a global organization that delivers care, aided by technology to help millions of people live healthier lives. The work you do with our team will directly improve health outcomes by connecting people with the care, pharmacy benefits, data and resources they need to feel their best. Here, you will find a culture guided by inclusion, talented peers, comprehensive benefits and career development opportunities. Come make an impact on the communities we serve as you help us advance health optimization on a global scale. Join us to start Caring. Connecting. Growing together.

You'll enjoy the flexibility to work remotely * from anywhere within the U.S. as you take on some tough challenges. For all hires in the Minneapolis or Washington, D.C. area, you will be required to work in the office a minimum of four days per week.

Primary Responsibilities:

• Lead design and delivery of modernized adjudication services, aligned to the program roadmap and target architecture
• Responsible for upholding engineering best practices and implementing appropriate architectural designs to deliver safe and robust solutions
• Build and enhance Java/Spring-based services and APIs supporting adjudication modernization initiatives
• Decompose legacy capabilities into modular, testable, independently deployable components (where appropriate), improving maintainability and delivery velocity
• Own end-to-end implementation for assigned modernization features: requirements clarification, technical design, build, test, release, and production support
• Partner with product, architecture, and downstream platform teams to ensure modernized components integrate cleanly with existing claim processing flows
• Implement robust observability (logs/metrics/traces), alerting, and SLO-focused engineering to improve reliability and operational readiness
• Drive performance and scalability improvements for claim transaction workflows (latency, throughput, resiliency, failure isolation)
• Establish and maintain technical documentation (designs, run-books, support procedures) for modernized services
• Perform impact assessment and gap analysis from reverse engineering efforts
• Drive cross-team technical coordination for delivery schedules, dependencies, and integration testing (internal and with partners/vendors, as applicable)
• Provide technical guidance into stakeholder communications (engineering impacts, release readiness, implementation constraints, risks, mitigations) using approved internal guidance
• Cloud, containers, and platform engineering (Azure AWS)
  • Design, build, and operate cloud-native services on Azure and/or AWS, selecting appropriate managed services and patterns for reliability and cost
  • Package and deploy applications using Docker and Kubernetes (K8s), applying secure configuration, resource tuning, and rollout strategies
  • Build/maintain CI/CD pipelines for automated build, test, security scanning, and deployment across environments
  • Improve infrastructure and deployment automation (IaC practices where used by the team), reducing manual steps and increasing repeatability
• AI engineering (prompt, agentic, harness) to accelerate delivery
  • Adoption of AI solutions in daily development workflow activities
  • Design and develop AI agents to automate/accelerate engineering and analysis tasks (e.g., code conversion, documentation, testing acceleration, migration support)
  • Apply AI prompt engineering and agentic AI patterns to create reliable task-oriented assistants with measurable outcomes
  • Be an AI champion within the team, encouraging and mentoring peers to leverage the power of AI to achieve solutions sooner
  • Build and maintain AI harness engineering capabilities (evaluation harnesses, regression suites, guardrails, telemetry) to ensure agent quality, safety, and repeatability
  • Integrate AI tooling into the developer workflow (CI hooks, PR checks, knowledge retrieval, standardized templates) to improve throughput and reduce defects
  • Establish operational controls for AI-enabled automation (access, logging, validation, fail-safes, human-in-the-loop where needed)
• Quality, security, and operational excellence
  • Champion engineering best practices: clean code, design reviews, automated testing (unit/integration/contract), and secure-by-design implementation
  • Diagnose and resolve complex production issues; perform root-cause analysis and implement preventative fixes
  • Ensure compliance with internal security, privacy, and SDLC controls (secrets management, vulnerability remediation, dependency hygiene)
• Collaboration and leadership expectations
  • Provide technical leadership for assigned initiatives: mentor engineers, unblock delivery, and raise the bar on engineering quality
  • Collaborate effectively across product, operations, architecture, and partner teams to deliver outcomes on schedule
  • Communicate progress, risks, and trade-offs clearly to stakeholders; escalate appropriately with mitigation options

You'll be rewarded and recognized for your performance in an environment that will challenge you and give you clear direction on what it takes to succeed in your role as well as provide development for other roles you may be interested in.

Required Qualifications:

• Bachelor's degree in Computer Science, Engineering, Information Technology, or a related technical field or equivalent practical experience
• 10 years of professional software engineering experience, with demonstrated ownership of complex, production critical systems
• 5 years leading development teams, delivering robust and safe solutions for enterprise systems
• Proven experience delivering large-scale, high-volume transactional systems
• Core Engineering Skills
  • Hands on experience designing and building cloud native applications deployed to Azure and/or AWS
  • Experience building and consuming APIs (REST, messaging, integration layers) supporting high volume transactional workloads
  • Demonstrated experience working on or integrating with pharmacy claims adjudication systems or similarly complex transaction processing platforms
  • Proven experience with Docker and Kubernetes (K8s), including containerized deployments, configuration, and runtime troubleshooting
  • Experience participating in cross team delivery efforts where missed deadlines introduce operational, financial, or compliance risk
  • Deep familiarity with CI/CD pipelines, automated testing, and secure SDLC practices expected in OptumRx Technology environments
  • Solid proficiency in Java and Spring / Spring Boot, delivering enterprise grade, production ready services.
  • Proven ability to implement changes driven by external standards or regulatory mandates, ensuring correctness, auditability, and system stability
• AI & Engineering Acceleration (Required for This Role)
  • Hands on experience with AI prompt engineering for software development, analysis, or automation use cases
  • Experience developing or applying agentic AI solutions to automate engineering workflows or accelerate delivery outcomes
  • Working knowledge of AI harness engineering concepts, including evaluation, regression, guardrails, and reliability considerations for AI assisted systems
  • Proven ability to integrate AI assisted solutions responsibly into enterprise engineering environments
• Operational & Quality Expectations
  • Strong production ownership mindset, including:
  • Troubleshooting and resolving complex issues
  • Root cause analysis
  • Implementing preventative improvements
  • Experience implementing observability (logging, metrics, alerts) aligned to mission critical system expectations
  • Commitment to secure coding, data protection, and privacy controls required in healthcare technology

Preferred Qualifications:

• Domain Experience
  • Experience supporting healthcare, PBM, or claims processing platforms, with an understanding of high availability and regulatory sensitive systems used in pharmacy or payer environments
  • Experience supporting legacy modernization initiatives, especially decomposing monolithic or mainframe adjacent systems into service based architectures
  • Familiarity with NCPDP transaction standards (e.g., D.0 and/or vF6) or experience delivering large scale standards migrations
• Cloud & Platform Depth
  • Experience operating in multi cloud environments (Azure AWS) with an understanding of resiliency and cost considerations at scale
  • Knowledge of infrastructure as code and automated environment provisioning used in OptumRx platforms
• Technical Leadership
  • Experience mentoring engineers and elevating technical quality across a team without formal people management responsibilities
  • Demonstrated ability to act as a technical leader or senior individual contributor, influencing architecture, design standards, and engineering best practices.
  • Proven ability to clearly communicate technical decisions, risks, and trade offs to both engineering and non engineering stakeholders
• Advanced AI Utilization
  • Experience designing repeatable, production safe AI agents for engineering or platform workflows.
  • Familiarity with applying AI tools to:
  • Code modernisation
  • Standards analysis and mapping
  • Documentation and knowledge acceleration
  • Test generation or validation

*All employees working remotely will be required to adhere to UnitedHealth Group's Telecommuter Policy

Pay is based on several factors including but not limited to local labor markets, education, work experience, certifications, etc. In addition to your salary, we offer benefits such as, a comprehensive benefits package, incentive and recognition programs, equity stock purchase and 401k contribution (all benefits are subject to eligibility requirements). No matter where or when you begin a career with us, you'll find a far-reaching choice of benefits and incentives. The salary for this role will range from $112,700 - $193,200 annually based on full-time employment. We comply with all minimum wage laws as applicable.

Application Deadline: This will be posted for a minimum of 2 business days or until a sufficient candidate pool has been collected. Job posting may come down early due to volume of applicants.

At UnitedHealth Group, our mission is to help people live healthier lives and make the health system work better for everyone. We believe everyone-of every race, gender, sexuality, age, location and income-deserves the opportunity to live their healthiest life. Today, however, there are still far too many barriers to good health which are disproportionately experienced by people of color, historically marginalized groups and those with lower incomes. We are committed to mitigating our impact on the environment and enabling and delivering equitable care that addresses health disparities and improves health outcomes - an enterprise priority reflected in our mission.    

UnitedHealth Group is an Equal Employment Opportunity employer under applicable law and qualified applicants will receive consideration for employment without regard to race, national origin, religion, age, color, sex, sexual orientation, gender identity, disability, or protected veteran status, or any other characteristic protected by local, state, or federal laws, rules, or regulations.

UnitedHealth Group is a drug - free workplace. Candidates are required to pass a drug test before beginning employment.