Senior Analyst - Medical Cost Strategy and Field Support

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.

Company: Oak Street Health 

Title: Senior Analyst - Medical Cost Strategy & Field Support

Location: Remote

Role Description:

At Oak Street Health, Population Health is central to our clinical outcomes and economic model, focused on delivering high‑quality, cost‑effective care. The Population Health Senior Analyst, Medical Cost Strategy & Field Support plays a key role in advancing Population Health priorities through the design and execution of high‑impact initiatives.

This role partners closely with clinicians, care teams, operations, and Treehouse teams (including Data Science and Finance) to implement targeted programs that improve quality and reduce medical costs. Focus areas include admission prevention, transitions of care, pharmacy and medication adherence, HEDIS/Stars performance, preferred partner strategies, and medical cost management.

The Senior Analyst acts as a cross‑functional leader, helping bridge centralized Population Health strategy with frontline execution across regions and centers. This is a fast‑paced, high‑visibility role requiring strong analytical skills, collaboration, and a bias toward execution and improvement.

This role reports to the Executive Director, Medical Cost Strategy & Field Support and partners closely with the Lead Directors leading field engagement and building a central program for Oak Street's highest-priority patients

Key Responsibilities

• Support medical cost management initiatives through data-driven analysis and performance tracking

• Develop executive-ready presentations and written analyses to communicate insights, progress, and recommendations

• Track progress against key initiatives, milestones, and outcomes; surface risks and opportunities proactively

• Provide general project and workstream management to ensure priorities are clearly defined and executed

• Identify workflow bottlenecks across field-based and central patient support teams; design practical solutions to improve efficiency and effectiveness

• Present workflow improvement recommendations and progress updates to senior leaders

• Act as a bridge between field support teams and centralized patient support functions to ensure alignment and smooth transitions

• Partner closely with leaders to build analyses and presentations for leadership and leadership support teams

Required Qualifications

• 2–5 years of relevant experience in consulting, healthcare, population health, provider-facing operations, or related fields

• Proven ability to build trust and credibility with diverse stakeholder groups across levels and functions

• Demonstrated track record of solving complex, ambiguous problems with practical, results-oriented solutions

• Strong financial and analytical skills, including experience developing business cases, ROI, and financial analyses

• Exceptional ability to synthesize large volumes of information into clear, concise insights and recommendations

• Proactive communicator who connects individual projects to broader organizational goals and cross‑functional priorities

• Highly organized, with the ability to manage multiple priorities simultaneously while maintaining a positive, professional attitude

• Comfortable working in fast-paced, ambiguous environments; quick learner with intellectual curiosity

• Advanced proficiency in MS Office, Google Workspace, and project management tools

• Persistent, thoughtful follow‑through with a collaborative and solutions-focused approach

• Embodies “Oaky” values

Preferred Experience & Skills

• Experience in value-based care models and medical cost management

• Strong background in population health strategy and operations

• Advanced PowerPoint skills, with the ability