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, 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.
4. Communication, Messaging & Executive Storytelling
• 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.
5. Program Leadership & Special Initiatives
• 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.
6. Organizational Health & Culture Leadership
• 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.
7. Decision Support & Prioritization
• 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.
Required Qualifications
• 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.
Preferred Qualifications
• 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.
Leadership Competencies
• Executive Presence: Operates with discretion, maturity, and high trust.
• Strategic Thinking: Converts vision into clear plans, priorities, and measurable outcomes.
• Collaboration & Influence: Aligns multiple senior leaders and cross-functional teams.
• Operational Excellence: Obsessed with clarity, execution rigor, and predictable results.
• Communication Mastery: Elite storyteller capable of simplifying complex information.

Pay Range

The typical pay range for this role is:

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls.  The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors.  This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above.  This position also includes an award target in the company’s equity award program. 
 

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in our comprehensive and competitive mix of pay and benefits – investing in the physical, emotional and financial wellness of our colleagues and their families to help them be the healthiest they can be. In addition to our competitive wages, our great benefits include:

• 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.

For more information, visit https://jobs.cvshealth.com/us/en/benefits

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.