Director Web Engineering

CVS Health • Denver, CO

7d

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. Bring your heart to CVS Health At CVS Health, we put people first, not just the millions of members we serve, but the teams who build the technology that supports them. As a Director of Web Engineering, you’ll lead high-impact engineering teams responsible for delivering reliable, accessible, and scalable digital experiences that help people navigate their health with confidence. This role blends strategic leadership, technical judgment, and people-first management. You’ll partner closely with Product, Design, Mobile, Platform, and AI teams to deliver outcomes, not just output, while building an environment where engineers can do the best work of their careers. The web experiences you help deliver will directly impact how millions of people access care, understand their benefits, and make informed decisions about their health. This role is an opportunity to shape not just technology, but the way teams work together with empathy, clarity, and purpose. Role overview The Director of Web Engineering is responsible for leading multiple web engineering teams across multiple product portfolios. You’ll own delivery, technical quality, and team health, while helping shape longer-term strategy and execution across the broader digital ecosystem. You will operate at both the systems level (org design, capacity planning, risk management) and the human level (coaching leaders, building trust, and developing talent). This role requires comfort navigating ambiguity, cross-team dependencies, and complex delivery environments, especially during high-stakes moments like Open Enrollment.

Requirements

• 10+ years of experience in software engineering, with significant experience building and delivering modern web applications.
• 5+ years of people leadership experience, including managing managers and senior technical leaders.
• Strong understanding of modern web architectures (e.g., component systems, micro-frontends, CI/CD pipelines).
• Proven ability to lead teams through complex delivery cycles, including high-visibility or time-sensitive initiatives.
• Experience partnering with Product, Design, and Platform teams in large, matrixed organizations.
• Demonstrated ability to balance technical excellence, delivery accountability, and people leadership.
• Comfort operating with ambiguity and evolving priorities, while maintaining clarity for your teams.
• Strong communication skills, with the ability to explain complex topics to both technical and non-technical audiences.

Nice To Haves

• Experience working in regulated or highly available environments (e.g., healthcare, finance, large-scale consumer platforms).
• Experience supporting large-scale redesigns, platform modernization, engineering processes, and system optimization.
• Familiarity with observability, experimentation, and feature flagging tools.
• Passion for mentorship, leadership development, and building inclusive teams.
• Excellent collaboration skills required to ideate solutions that are sufficient and feasible to both the business leads and the technical teams.
• Exceptional organizational, analytical, problem-solving, strategic thinking, and time management abilities.
• Experience with optimization skills to improve performance, scalability, and usability of our applications.
• Open-minded to new ideas & approaches, and ability to implement the ideas using various technologies.
• A self-starter that is naturally inquisitive.
• Experience with agile development, SAFe Agile experienced preferred

Responsibilities

• Lead and develop engineering managers and staff level engineers, fostering a culture of trust, accountability, and continuous improvement.
• Own delivery outcomes for web initiatives, ensuring commitments are based on realistic capacity, clear dependencies, and sound technical plans.
• Partner closely with Product and Design leaders to align on priorities, scope, and sequencing - translating strategy into executable plans.
• Guide technical direction across our tech stack (e.g., TypeScript, React, Redux, playwright), balancing innovation with stability.
• Drive operational excellence through strategic planning, observability, security, and post-incident learning
• Anticipate and manage delivery risk, especially in complex, cross-team environments with shared services and dependencies.
• Support hiring, onboarding, and talent development, while ensuring teams are structured to scale sustainably.
• Represent web engineering in executive and cross-functional forums, communicating clearly, calmly, and with credibility.
• Champion inclusive, accessible, and member-centric digital experiences that align with CVS Health values.

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
• Number of Employees: 5,001-10,000 employees