Lead Director, Software Engineering

CVS Health

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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. Job Summary We are seeking a seasoned Lead Director of Software Engineering to oversee the strategy, delivery, and modernization of our Sales Enablement Platform. This leader will drive the evolution of key components supporting Medicare sales operations, managing hybrid engineering teams responsible for on‑premise systems and guiding the migration toward a modern, cloud‑based technology stack. The role requires strong technical leadership, people management, and the ability to partner closely with business stakeholders to ensure platforms meet the needs of Medicare sales, field agents, and internal sales channels.

Requirements

• 10+ years of experience in software engineering, software delivery, or technical leadership roles.
• 3–5 years of direct leadership experience managing managers and hybrid engineering teams.
• Demonstrated success leading modernization programs, including migration of on‑prem applications to cloud platforms.
• Experience running large‑scale platforms supporting sales, operations, or similarly critical enterprise functions.
• Strong understanding of modern delivery practices including Agile, DevOps, automation, and continuous improvement.
• Excellent communication skills with the ability to influence technical and business stakeholders across the organization.
• Experience managing budgets, vendor relationships, and enterprise‑level delivery commitments.
• Bachelor’s degree in Computer Science, Engineering, Information Systems, or a related technical field required.

Nice To Haves

• Experience supporting agent‑facing or sales enablement platforms in regulated industries.
• Familiarity with customer data platforms (CDPs), enterprise data strategy, or marketing/sales data ecosystems.
• Background in modernization of legacy systems, microservices, or cloud‑native architectures.
• Experience leading distributed or cross‑time‑zone engineering teams.
• Master’s degree in Computer Science, Engineering, or related field.

Responsibilities

• Provide strategic and hands‑on leadership for engineering teams supporting the Sales Enablement Platform, including on‑premise systems and planned cloud migration initiatives.
• Lead a hybrid, cross‑time‑zone engineering organization, managing managers, contractors, and full‑time engineers.
• Define, plan, and execute modernization roadmaps in partnership with product, architecture, security, compliance, and Medicare sales business stakeholders.
• Ensure delivery excellence through modern engineering and delivery practices, including Agile, DevOps, CI/CD, and quality automation.
• Drive platform stability, scalability, and performance across sales workflows, agent-facing tools, and supporting services.
• Oversee budget planning, vendor management, resource allocation, and long‑term capacity planning.
• Ensure compliance with enterprise policies, Medicare regulatory requirements, HIPAA, and other applicable standards.
• Promote engineering best practices, talent development, and a culture of accountability and continuous improvement.
• Partner with enterprise data teams to align platform capabilities with broader data strategy; experience with CDP ecosystems considered a plus.
• Participate in roadmap planning, portfolio management, and cross‑functional leadership forums to ensure strong alignment with business objectives.

Benefits

• Affordable medical plan options, a 401(k) plan (including matching company contributions), and an employee stock purchase plan.
• No-cost programs for all colleagues including wellness screenings, tobacco cessation and weight management programs, confidential counseling and financial coaching.
• Benefit solutions that address the different needs and preferences of our colleagues including paid time off, flexible work schedules, family leave, dependent care resources, colleague assistance programs, tuition assistance, retiree medical access and many other benefits depending on eligibility.

What This Job Offers

• Job Type: Full-time
• Career Level: Director