Executive Director, Engineering - AI Automation

CVS Health • Wellesley, MA

1d

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 Executive Director of Engineering - AI Automation will lead a 50+ person organization responsible for architecting, developing, and scaling enterprise AI-driven automation and augmentation solutions for contact centers. This team spans data engineering, software engineering, Generative AI implementation, and application integration. The role partners closely with Data Science, Product, and vertical IT organizations to deliver high-impact AI capabilities that improve customer experience, operational efficiency, and agent enablement. This leader sets the engineering strategy, drives execution excellence, and ensures delivery of high-quality, secure, and reliable platforms. The Executive Director is accountable for shaping engineering vision, developing high-performing leaders, and guiding teams through complex, large-scale AI product development in a fast-evolving technology landscape.

Requirements

• 10+ years of experience in software engineering, platform engineering, or AI/ML development, including 5+ years in senior engineering leadership roles.
• Hands-on experience delivering enterprise-scale AI systems in production environments.
• Proven ability to scale customer-facing platforms with strong reliability, resilience, and security best practices.
• Deep knowledge of modern engineering practices (cloud-native architectures, CI/CD automation, observability, SRE principles).
• Strong stakeholder influence skills, especially in partnering with Data Science and Product organizations.
• Demonstrated people leadership experience, building and growing high-performing engineering cultures.
• Bachelor’s degree in engineering, computer science, physics, mathematics, or a related quantitative discipline.

Nice To Haves

• Experience delivering AI-enabled contact center capabilities (Voice AI, NLP, ML platforms) in production environments.
• Background working in regulated industries with strong privacy and security requirements.
• Experience integrating AI technologies into large, distributed enterprise ecosystems.
• Graduate degree preferred.

Responsibilities

• Lead a multi-disciplinary engineering organization delivering AI-enabled automation and augmentation for enterprise contact centers.
• Define engineering strategy across AI platforms, data pipelines, software systems, and integration architectures.
• Partner with Data Science and Product teams to translate business outcomes into scalable, production-grade AI systems.
• Drive engineering excellence, including reliability, security, code quality, CI/CD, and observability/SRE standards.
• Oversee the execution of platform roadmaps, ensuring timely delivery, adoption, and operational performance.
• Develop and mentor engineering leaders, fostering a culture of innovation, accountability, and continuous improvement.
• Ensure alignment with enterprise architecture and successfully integrate AI solutions into broader IT ecosystems.
• Manage budgets, vendor partnerships, and resource planning across a large engineering portfolio.
• Engage senior stakeholders to influence strategy, negotiate trade-offs, and drive alignment across complex organizational structures.

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: Executive