Chief of Staff - Caremark Digital Technology

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. Key Responsibilities 1. Executive Enablement & Strategic Advisory • Serve as a trusted advisor to the VP, providing insight, analysis, and recommendations on priorities, risks, and organizational effectiveness. • Translate the VP’s strategic vision into executable plans, workstreams, and targets for all Digital Technology pillars. • Support enterprise-wide digital modernization initiatives by driving cross-functional clarity and alignment. 2. Operating Rhythm & Leadership Cadence • Design, implement, and continuously optimize the operating rhythm for Digital Technology. • Lead preparation and follow-ups for leadership meetings, QBRs, MBRs, program reviews, and executive discussions. • Own the management of OKRs, KPIs, dashboards, and performance tracking across all digital domains. 3. Cross-Functional Orchestration • Serve as the connective tissue between Technology, Architec...