COO Jobs in Chicago, IL

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.

Position Summary

CVS Health is seeking a highly strategic Executive Director, Chief of Staff, reporting to the Senior Vice President, Chief Operating Officer for Pharmacy Services. This leader will be responsible for shaping, and advancing key business priorities, translating strategy into coordinated execution, and strengthening accountability and operating discipline across the organization.

The Chief of Staff will serve as a strategic thought partner to the Chief Operating Officer for Pharmacy Services and his direct leadership team. This leader will play a critical role in driving clarity, alignment, and execution on initiatives of substantial scale, visibility and complexity. This individual will bring structure to complex business issues, anticipate risks and opportunities, and help ensure focus on the initiatives with the greatest operational, financial, client, and enterprise impact.

Key Responsibilities

Strategy Development and Execution

• Partner with the Chief Operating Officer to shape strategic priorities and translate them into actionable plans and measurable business outcomes.
• Lead complex, high-visibility, cross-functional initiatives spanning multiple teams and business areas.
• Ensure organizational priorities align with broader Pharmacy Services and enterprise objectives.
• Anticipate barriers, identify risks, and coordinate timely resolution of issues affecting business performance.
• Monitor progress against strategic commitments and drive corrective action when priorities or outcomes are at risk.

Business Management and Governance

• Establish and manage operating cadence, governance, and decision-making processes.
• Maintain visibility into strategic priorities, dependencies, risks, and performance.
• Establish reporting and performance management routines that strengthen accountability and execution.
• Partner with finance and analytics teams to support business planning, budgeting, investment prioritization, and resource allocation.
• Identify opportunities to improve processes, organizational effectiveness, and operating performance.
• Lead planning for leadership meetings, business reviews, town halls, and other key forums, ensuring clear decisions and follow-through.

Executive Communications, Insights, and Decision Support

• Serve as a trusted advisor and thought partner to the Chief Operating Officer.
• Frame complex business issues, evaluate options, and develop clear recommendations for executive decision-making.
• Develop executive-level presentations, briefings, communications, and other materials for senior leadership and key stakeholders.
• Connect leaders with functional and delivery teams to support alignment, accountability, and execution.
• Build strong relationships across Pharmacy Services and the enterprise to advance shared priorities.
• Support the Chief Operating Officer in key meetings and cross-functional forums, as appropriate.
• Handle sensitive business matters with sound judgment, discretion, and confidentiality.

Required Qualifications

• 10+ years of leadership experience in business operations, strategy, management consulting, transformation, program leadership, or a related discipline.
• Demonstrated experience shaping strategy and translating priorities into coordinated execution and measurable business results.
• Proven success leading complex, enterprise-wide, cross-functional initiatives in a large, matrixed organization.
• Strong business, financial, operational, and analytical acumen.
• Experience establishing governance, management routines, and accountability across a complex organization.
• Demonstrated ability to partner with senior executives and influence across organizational boundaries.
• Exceptional written and verbal communication skills, including developing executive-level presentations and recommendations.
• Strong judgment and problem-solving capabilities, with the ability to bring clarity and structure to complex or ambiguous situations.
• Ability to build effective relationships and work across all levels of the organization.
• Experience within pharmacy services, pharmacy benefit management, healthcare, regulated industries, or complex service operations highly valued.
• Bachelor’s degree required; advanced degree preferred.

Preferred Qualifications:

• Advanced degree (Masters or MBA).
• Prior experience in Management Consulting, a Chief of Staff role, or internal strategy team.
• Experience supporting or advising SVP+ leadership.

Pay Range

The typical pay range for this role is:

$131,500.00 - $303,195.00

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 offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 10/09/2026

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