Chief of Staff - Caremark - Digital Technology

At CVS Health, we're building a world of health around every consumer and surrounding ourselves with dedicated colleagues who are passionate about transforming health care. As the nation's leading health solutions company, we reach millions of Americans through our local presence, digital channels and more than 300,000 purpose-driven colleagues - caring for people where, when and how they choose in a way that is uniquely more connected, more convenient and more compassionate.

And we do it all with heart, each and every day.

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/Dev Ops/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.

• 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, work streams, and targets for all Digital Technology pillars.
• Support enterprise-wide digital modernization initiatives by driving cross-functional clarity and alignment.

• 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.

• Serve as the connective tissue between Technology, Architecture, Product, HR, Security, Finance, and CDTO organizations.
• Ensure alignment on priorities, resource allocation, and dependencies across Digital Experience, Platform, AI, Integration, and SRE.
• Unblock cross-team issues and create predictability in execution across digital programs.

• Develop executive-level presentations, strategy documents, communications, and business narratives for internal and external audiences.
• Craft crisp messaging for digital transformation programs, leadership updates, operating model changes, and investment cases.
• Ensure consistent and high-quality communications across all levels of the organization.

• Lead high-impact, VP-sponsored initiatives spanning digital modernization, platform engineering, AI adoption, org design, and operational uplift.
• Drive program execution rigor, including milestones, timelines, risk management, and stakeholder alignment.
• Manage confidential and sensitive initiatives that require executive discretion and precision.

• Serve as a culture champion - driving clarity, transparency, collaboration, and continuous improvement across Digital Engineering.
• Monitor team morale, workload balance, role clarity, and leadership alignment.
• Partner with HR on talent strategy, staffing, onboarding, headcount planning, and succession pipelines.

• Triaging decisions, aligning stakeholders, and ensuring the VP focuses on the highest-leverage activities.
• Prepare briefing materials, analysis, insights, and recommendations for complex decision-making.
• Represent the VP in key meetings when needed to drive continuity and alignment.

• 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, Dev Ops, SRE, platform engineering, data, and AI.
• Exceptional…