CVS Health · 2 days ago
Chief of Staff - Caremark - Digital Technology
United States
Full-time
Remote
Director/Executive
$144K/yr - $288K/yr
12+ years expCVS Health is the nation’s leading health solutions company, dedicated to transforming health care. The Chief of Staff for Digital Technology will serve as a strategic partner to the VP of Digital Engineering, driving alignment and operational excellence across the digital transformation agenda.
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Responsibilities
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
Qualification
Required
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
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
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.
Company
CVS Health
CVS Health is a health solutions company that provides an integrated healthcare services to its members.
10001+ employees
H1B Sponsorship
CVS Health has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2022 (1)
Funding
Current Stage
Public CompanyTotal Funding
$4BKey Investors
Michigan Economic Development CorporationStarboard Value
2025-08-15Post Ipo Debt· $4B
2025-07-17Grant· $1.5M
2019-11-25Post Ipo Equity
Leadership Team
David Joyner
President and Chief Executive Officer, CVS Health
Chandra McMahon
SVP & CISO
Recent News
Maryland Daily Record
2026-01-19
bloomberglaw.com
2026-01-16
Company data provided by crunchbase