Software engineering manager Jobs in Chicago, IL

Lead Director Of Software Engineering

We're building a world of health around every individual shaping a more connected, convenient and compassionate health experience. At CVS Health, you'll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger helping to simplify health care one person, one family and one community at a time.

Health100 is America's trusted front door to health and care. The Health100 platform integrates any participating health plan, PBM, pharmacy (retail and specialty), provider, digital health point solution provider, and employer, and addresses the top health care challenges for the consumer.

We are looking for a hands-on, passionate engineering leader to join a high-energy, mission-driven team on the forefront of digital health innovation reinventing how consumers engage with their health. As the Lead Director of Software Engineering, you will lead the strategic vision, development, and execution of our platform engineering roadmap. You will drive innovation, manage cross-functional teams, and ensure the delivery of high-quality products that exceed consumer expectations.

As a key strategic leader, you will own integration strategy and execution across multiple domains, managing partner requirements, technical constraints, and external commitments while advancing platform modernization initiatives. You will partner closely with external stakeholders, understand their technical constraints and success criteria, and communicate risks and feasibility clearly in both technical and business terms.

Responsibilities:

• Strategic & technology roadmap ownership: Define and drive multi-team product and technical roadmaps, aligning engineering investments, architectural direction, and delivery priorities with business outcomes
• Engineering excellence & delivery governance: Establish scalable engineering standards, operational frameworks, and risk management practices to ensure quality, efficiency, and reliable execution across teams
• Organizational leadership & talent strategy: Lead, mentor, and grow engineering managers and senior engineers, owning hiring, performance management, career development, succession planning, and a culture of accountability and high performance
• Cross-functional and external stakeholder alignment: Partner closely with Product, Business, Architecture, Design, Security, and external partners to translate strategy into executable programs with clear milestones, accountable ownership, and measurable outcomes
• Technical complexity and ambiguity navigation: Own architecturally complex initiatives across multiple domains, guiding teams through evolving requirements, tight dependencies, and external commitments that require disciplined execution and sound technical judgment
• Resource scaling and innovation: Manage vendor and contingent workforce strategies while leading technology research across AI, cloud, and distributed systems to inform long-term platform investments, optimize integrations, and improve operational outcomes

Required Qualifications

• 12+ years of hands-on software engineering experience in large-scale distributed platforms, including complex integration and interoperability challenges; 5+ years of experience leading managers and senior engineers through complex technical initiatives
• Proven delivery of large-scale, multi-team engineering programs, owning strategy through execution across complex integrations, platform modernization, and cloud migrations in fast-paced digital or healthcare technology environments
• Strong technical depth in distributed systems and cloud-native architectures, including microservices (Java/Spring Boot, Python), DevOps (CI/CD, Kubernetes/Docker), and cloud platforms (GCP preferred)
• Executive-level communication and influence skills and demonstrated success building and scaling high-performing engineering organizations, including distributed teams and vendor partnerships
• Hands-on experience delivering AI-enabled or generative AIintegrated software solutions that produced measurable business or operational outcomes

Preferred Qualifications

• Proven experience hiring and leading high-performing, distributed engineering teams, including multi-site and fully remote models
• Demonstrated data-driven problem solving, using quantitative analysis to guide decisions and improve outcomes
• Hands-on experience defining, tracking, and analyzing KPIs to measure engineering productivity, delivery health, and project success
• Experience delivering healthcare or wellness technology solutions, working effectively with both onshore and offshore teams

Education

• Bachelor's degree in Computer Science, Information Systems, Engineering, related field, or equivalent experience (High school diploma plus 4 years relevant work experience)

Pay Range

The typical pay range for this role is:

$144,200.00 - $288,400.00

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company's equity award program.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This full?time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well?being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.