Senior Manager Software Development Engineering Modernization

CVS Health•Northbrook, IL

8d•$118,450 - $260,590

About The Position

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. Position Summary The Senior Manager Modernization will lead Integration Engineering Platform modernizations by transforming legacy applications into scalable, cloud-native solutions using AI-assisted, automation-first approaches. The role drives end-to-end initiatives including certificate management, refactoring, re-platforming, and microservices decomposition, leveraging GenAI for code analysis, dependency mapping, and accelerated migration. It ensures modernization improves scalability, resilience, performance, and cost efficiency while aligning with enterprise standards. The function embeds automation and AI across the SDLC to enhance speed, quality, and reduce technical debt. It also advances AIOps, observability, and operational stability, delivering resilient systems and measurable business value through sustained modernization outcomes.

Requirements

7+ years of software engineering experience, with people and delivery leadership
5+ years leading large‑scale modernization or platform transformation programs.
Strong experience modernizing legacy systems using cloud, automation, and AI‑assisted techniques
Solid understanding of microservices, event‑driven systems, API design, and integration patterns
Hands‑on experience with Azure, AWS, or GCP, and platforms such as Kafka, API Management, containers, and CI/CD pipelines
Experience applying automation and AI across development, testing, and operations
Proven ability to lead teams in Agile and DevOps environments

Nice To Haves

Experience using GenAI/LLMs for code analysis, refactoring, documentation, or test generation
Background in healthcare, PBM, or other regulated enterprise environments
Experience modernizing middleware platforms such as IBM ACE, MQ, DataPower, or API Integrated systems
Exposure to AIOps, intelligent monitoring, and automated incident management
Experience managing globally distributed engineering teams

Responsibilities

Lead and manage software development teams modernizing legacy applications using AI‑assisted and automation‑driven workflows
Manage the Work Intake from Business teams and ensure timely delivery of projects that will meet their business needs
Own end‑to‑end delivery of modernization initiatives, including re‑platforming, re‑factoring, strangler patterns, and selective rewrites, accelerated through automation
Drive predictable, high‑quality delivery using Agile and DevOps practices enhanced with automated pipelines and AI insights
Ensure modernization outcomes improve scalability, resiliency, performance, and developer productivity
Define and execute AI‑driven modernization strategies, including: GenAI‑assisted code analysis, refactoring, and documentation. Automated dependency discovery and application decomposition. AI‑supported framework upgrades and language modernization.
Leverage automation and AI tools to accelerate migration of legacy middleware, batch, and monolithic applications to cloud‑native and microservices architectures
Apply intelligent testing and validation techniques to reduce regression risk during large‑scale transformations
Partner with architecture and platform teams to ensure AI usage aligns with enterprise standards, security, and governance
Lead adoption of modern platforms across Azure, AWS, and GCP
Promote API‑first and event‑driven designs enhanced by automation for provisioning, scaling, and deployment
Drive pipeline automation to standardize cloud environments and reduce manual effort
Manage the Software footprint with Security & Compliance upgrades and Framework updates
Ensure new solutions meet enterprise requirements for security, compliance, performance, and cost optimization
Champion automation across the SDLC, including build, test, deployment, and runtime operations
Collaborate with SRE and operations teams to introduce AIOps capabilities for proactive monitoring, anomaly detection, and faster incident resolution
Improve observability using AI‑driven insights across logs, metrics, and traces
Ensure modernization efforts improve production stability and operational resilience
Partner with product owners and business leaders to align AI‑driven modernization roadmaps with enterprise priorities
Communicate progress, risks, and outcomes using metrics, KPIs, and automation‑derived insights
Balance speed of delivery with risk management in highly regulated environments
Support budgeting, capacity planning, and vendor execution related to modernization and automation initiatives
Build and lead high‑performing teams skilled in cloud engineering, integration, AI‑assisted development, and automation
Coach engineers and tech leads on modern engineering practices and responsible AI usage
Drive skills transformation through upskilling plans focused on cloud, automation, and AI technologies
Lead hiring for full‑time and contract roles and manage onshore/offshore vendor partnerships