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CVS Health logo
CVS Health

CVS Health is a leading healthcare company operating CVS Specialty, CVS Pharmacy, CVS MinuteClinic, and CVS Caremark. In 2018, CVS combined forces with healthca

Chief of Staff – Digital Technology

Location

Arizona + 2 moreAll locations: Arizona | California | New Jersey

Posted

106 days ago

Salary

$144.2K - $288.4K / year

Seniority

Lead

Bachelor Degree12 yrs expEnglishCloud

Job Description

Chief of Staff – Digital Technology

CVS Health

• 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. • 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.

Job 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.
  • MBA or master’s degree in engineering, technology management, or related field is preferred.
  • Experience in healthcare, PBM, insurance, or financial services is preferred.

Benefits

  • medical, dental, and vision coverage
  • paid time off
  • retirement savings options
  • wellness programs

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United States
Job Closed