Full Time Remote Lead Software Engineer Jobs in Chicago, IL

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Why Join Enterprise Observability Engineering?
The Enterprise Observability Engineering team is a high-impact, high-autonomy group focused on building intelligent, scalable, and resilient observability solutions. We foster a culture of innovation, agility, and ownership-empowering engineers to solve complex problems, drive strategic initiatives, and shape the future of how we monitor and operate distributed systems.
If you're passionate about building tools engineers love, solving unscoped challenges, and leading with technical excellence-this is the team for you.

About the Role

We're looking for a Lead Software Engineer with deep expertise in logging and observability engineering. You should be fluent in the principles of open telemetry, log ingestion, and event correlation across distributed systems. While familiarity with platforms like Splunk or Dynatrace is a plus, we value platform-agnostic thinking and the ability to design resilient, scalable logging solutions using the best-fit tools for the environment.

As a Lead Software Engineer, you will drive the design, implementation, and evolution of our observability and logging platforms. You'll lead enterprise-scale initiatives, mentor engineers, and collaborate across disciplines to ensure our systems are reliable, scalable, and performant. Applying deep technical expertise to solve real-world challenges. You'll work closely with SRE, Security, Networking, Platform Engineering, and Data Science teams to evolve our observability strategy using AI/ML and cloud-native technologies.

Key Responsibilities

Architect and optimize observability environments through software engineering best practices.

Build automation scripts and tools to streamline observability instrumentation and deployment.

Integrate observability into CI/CD pipelines using infrastructure-as-code (IaC) and configuration management tools.

Conduct observability code reviews and implement automated validation checks.

Build AI-native tools for autonomous issue detection and resolution.

Lead the design of distributed systems focused on reliability, scalability, and performance.

Manage data routing, transformation, and endpoint monitoring integrations.

Mentor junior engineers and foster a culture of continuous improvement.

Collaborate across teams to align observability strategies with business goals.

Communicate technical insights and recommendations to leadership.

Use your skills to make an impact

Required Qualifications

• Associate degree in Computer Science, Engineering, or related field.
• 7+ years in software/infrastructure engineering with observability/logging focus.
• Strong foundation in operating systems, networking, algorithms, and distributed systems.
• Expertise in:

o Programming (eg. Python, .Net, Java, Go, Node.js)

o System architecture and AI Ops

o CI/CD (eg. GitHub Actions, Azure DevOps)

o Infrastructure as Code (eg. Terraform, Ansible)

o Cloud-native development (eg. Azure, AWS, GCP)

o API design (eg. REST, gRPC)

• Proven leadership and mentoring experience.
• Agile delivery experience and strategic thinking around observability maturity.

Preferred Qualifications

• 5+ years with a technical bachelor's degree
• Open telemetry
• Experience with Splunk Enterprise & ES (SPL, dashboards, correlation searches, data models)
• Scaled and complex Data onboarding (HEC, UF, TA development)
• Integration with SNOW, SOAR, ITSM/SecOps tools
• Experience with Dynatrace, Cribl, Grafana
• Monitoring and alerting strategy design
• Budget management and cost optimization
• Automation and continuous delivery practices
• Leading cross-functional programs across technologies
• Certified Splunk Admin and Advanced Power User

Additional Information

This position follows a remote work style however the candidate must live a commutable distance to one of our designated IT locations: Louisville, KY; Tampa, FL; Fort Laurderdale FL; Dallas, TX; Boston, MA; New York City; Washington, D.C; Atlanta, GA; Nashville, TN; Chicago, IL or Charlotte, NC.

Work at Home Requirements: To ensure Home or Hybrid Home/Office employees' ability to work effectively, the self-provided internet service of Home or Hybrid Home/Office employees must meet the following criteria: At minimum, a download speed of 25 Mbps and an upload speed of 10 Mbps is required; wireless, wired cable or DSL connection is suggested. In certain roles, the minimum recommended internet speed required by Humana may not be sufficient for business needs. Humana reserves the right to require associates to upgrade their internet service if necessary. Work from a dedicated space lacking ongoing interruptions to protect member PHI / HIPAA information.Travel: While this is a remote position, occasional travel to Humana's offices for training or meetings may be required.

Scheduled Weekly Hours

40

Pay Range

The compensation range below reflects a good faith estimate of starting base pay for full time (40 hours per week) employment at the time of posting. The pay range may be higher or lower based on geographic location and individual pay will vary based on demonstrated job related skills, knowledge, experience, education, certifications, etc.

$129,300 - $177,800 per year

This job is eligible for a bonus incentive plan. This incentive opportunity is based upon company and/or individual performance.

Description of Benefits

Humana, Inc. and its affiliated subsidiaries (collectively, "Humana") offers competitive benefits that support whole-person well-being. Associate benefits are designed to encourage personal wellness and smart healthcare decisions for you and your family while also knowing your life extends outside of work. Among our benefits, Humana provides medical, dental and vision benefits, 401(k) retirement savings plan, time off (including paid time off, company and personal holidays, paid parental and caregiver leave), short-term and long-term disability, life insurance and many other opportunities.
About us
About Humana: Humana Inc. (NYSE: HUM) is a leading U.S. healthcare company. Through our Humana insurance services and our CenterWell healthcare services, we make it easier for the millions of people we serve to achieve their best health - delivering the care and service they need, when they need it. These efforts are leading to a better quality of life for people with Medicare and Medicaid, families, individuals, military service personnel, and communities at large. Learn more about what we offer atHumana.comand atCenterWell.com.

Equal Opportunity Employer

It is the policy of Humana not to discriminate against any employee or applicant for employment because of race, color, religion, sex, sexual orientation, gender identity, national origin, age, marital status, genetic information, disability or protected veteran status. It is also the policy of Humana to take affirmative action, in compliance with Section 503 of the Rehabilitation Act and VEVRAA, to employ and to advance in employment individuals with disability or protected veteran status, and to base all employment decisions only on valid job requirements. This policy shall apply to all employment actions, including but not limited to recruitment, hiring, upgrading, promotion, transfer, demotion, layoff, recall, termination, rates of pay or other forms of compensation and selection for training, including apprenticeship, at all levels of employment.