Urgently Hiring Python Developer Apprenticeship Jobs in Chicago, IL

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 an AI‑native health technology platform that unifies pharmacies, providers, insurers, PBMs, and digital health solutions into a single, consumer‑focused ecosystem. Powered by Google Cloud AI, we're reimagining personalized and connected health experiences.

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 partner deeply with stakeholders across Health100 and CVS Health to understand consumers, current product landscape, operational needs, and business goals - developing long‑term visions, technical strategies, and roadmaps that deliver value. Design thinking is at the center of all you do, ensuring consumer centricity is the core of everything we build so that we deliver the right value to the right person at the right time.

*Preference is for candidates to work hybrid out of our corporate headquarters in Woonsocket, RI; remote will be considered for candidates not in close proximity to an office.

• 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.
• Stakeholder & cross‑functional alignment: Partner closely with Product, Business, Architecture, Design, Security, and executive leaders to translate strategy into executable programs with clear milestones and measurable outcomes.
• Resource scaling & innovation: Manage vendor and contingent workforce strategies while leading technology research and innovation across AI, cloud, and distributed systems to inform long‑term platform investments.

• 12+ years of software engineering experience, including 5+ years leading managers and senior engineers in Agile, cloud‑native environments.
• Proven delivery of large‑scale, multi‑team engineering programs, owning strategy through execution in fast‑paced digital or healthcare technology organizations.
• 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).
• Demonstrated success building and scaling high‑performing engineering organizations, including distributed teams (onshore/offshore/nearshore) and vendor partnerships.
• Executive‑level communication and influence skills, with hands‑on or applied experience (1+ year) delivering AI-enabled or generative AI‑integrated software solutions.

• 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.
• Practical experience with AI/ML technologies, including algorithms, frameworks, or applied tools in production or near‑production environments.
• Experience delivering healthcare or wellness technology solutions, working effectively with both onshore and offshore vendor teams.

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

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.

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.

We anticipate the application window for this opening will close on: 08/04/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.