Chief of Staff - Caremark Digital Technology

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. The Chief of Staff, Digital Technology serves as the strategic partner and right hand to the VP of Digital Engineering, enabling alignment, execution, and operational excellence across Caremark’s digital transformation agenda. This role orchestrates the Digital Technology operating model — spanning Digital Experience, Digital Platform Engineering, Digital AI Platform, Digital Client Integrations, SRE/DevOps/Automation, and Digital Architecture. The Chief of Staff drives prioritization, communication, cross-functional collaboration, and strategic program management. This ensures that the VP and the organization operate at maximum clarity, velocity, and impact.

Requirements

• 12+ years of experience in digital product, engineering, technology strategy, program leadership, or operations.
• Experience supporting senior executives or leading cross-functional technology programs.
• Deep understanding of modern digital engineering, including cloud, APIs, DevOps, SRE, platform engineering, data, and AI.
• Exceptional written and verbal communication skills with the ability to synthesize complexity.
• Proven ability to lead through influence in large, matrixed organizations.
• Strong analytical, problem-solving, and strategic planning skills.

Nice To Haves

• MBA or master’s degree in engineering, technology management, or related field.
• Experience in healthcare, PBM, insurance, or financial services.
• Familiarity with digital modernization, cloud migration, or enterprise-scale platform initiatives.

Responsibilities

• Executive Enablement & Strategic Advisory
• Operating Rhythm & Leadership Cadence
• Cross-Functional Orchestration
• Communication, Messaging & Executive Storytelling
• Program Leadership & Special Initiatives
• Organizational Health & Culture Leadership
• Decision Support & Prioritization

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