About The Position

The Lead Director, Provider Operations and Strategy serves as the principal strategic and operational advisor to the Chief Medical Officer (CMO), helping advance enterprise clinical priorities through strategic planning, executive communications, cross-functional leadership, and disciplined execution. The role promotes alignment across the provider organization, facilitates key initiatives, and helps maintain focus on important clinical and business priorities. It collaborates with physician leaders, operational partners, and corporate stakeholders to turn strategy into action, monitor progress, and support organizational effectiveness. As an extension of the CMO, the Lead Director contributes to executive communications, strategic planning, governance, and special projects in support of Oak Street Health’s clinical mission and organizational goals. The role partners with clinical, operational, finance, technology, people, and transformation teams, and serves as a thought partner to the CMO and senior clinical leaders. The position requires a bachelor’s degree and at least 10 years of progressive experience in healthcare strategy, clinical operations, provider operations, management consulting, healthcare transformation, or related fields. A relevant master’s degree and experience supporting executive leaders, strategic planning, or organizational transformation are preferred. The listed base pay range is $100,000 to $231,540, and the position may also be eligible for a CVS Health bonus, commission, or short-term incentive program and an equity award target. This full-time position is eligible for a comprehensive benefits package, subject to eligibility.

Requirements

  • Bachelor’s degree required.
  • 10+ years of progressive experience in healthcare strategy, clinical operations, provider operations, management consulting, healthcare transformation, or related fields.
  • Experience leading complex cross-functional initiatives and influencing leaders in a matrixed organization.
  • Strong understanding of healthcare delivery models, provider operations, value-based care, and clinical performance improvement.
  • Demonstrated ability to manage multiple high-priority initiatives simultaneously in a fast-paced environment.
  • Exceptional written and verbal communication skills, including development of executive-level presentations and strategic communications.
  • Experience facilitating senior leadership discussions and driving alignment among diverse stakeholder groups.
  • Ability to influence without direct authority and build trusted partnerships across functions and organizational levels.

Nice To Haves

  • Master’s degree in Healthcare Administration, Business Administration, Public Health, Healthcare Management, or a related field.
  • Experience supporting executive leaders, strategic planning efforts, or organizational transformation initiatives.
  • Strategic planning, project management, and change management experience.

Responsibilities

  • Partner with the CMO to advance provider-organization strategic priorities, providing analysis, recommendations, and execution support for clinical and operational initiatives.
  • Coordinate and drive cross-functional initiatives supporting provider operations, workforce engagement, clinical excellence, and organizational performance.
  • Support development and execution of strategic plans, annual goals, and enterprise clinical priorities, aligning organizational objectives with operational activities.
  • Lead complex projects on behalf of the CMO from concept through implementation, establishing timelines, stakeholder engagement plans, success metrics, and accountability mechanisms.
  • Collaborate with clinical, operational, finance, technology, people, and transformation teams to execute strategic initiatives and address organizational challenges.
  • Develop executive communications, presentations, leadership updates, and strategic materials for senior leadership meetings, governance forums, and organizational communications.
  • Synthesize data from multiple sources to identify trends, opportunities, and risks related to provider performance, engagement, workforce effectiveness, and clinical operations.
  • Support leadership governance processes, including preparation for executive meetings, strategic reviews, and decision-making forums.
  • Build stakeholder relationships and facilitate shared ownership and alignment around organizational priorities and outcomes.
  • Monitor initiative progress, identify execution barriers, and work with organizational leaders to develop solutions and drive accountability.
  • Partner with clinical leadership to establish key performance indicators and measurement frameworks supporting organizational goals and provider excellence.
  • Assess external market trends, healthcare industry developments, and regulatory changes to inform strategic recommendations and organizational planning.
  • Support change management and communications for provider-facing initiatives, organizational transformation, and clinical operational improvements.
  • Identify opportunities to improve organizational effectiveness, leadership communication, and execution capabilities across the provider organization.
  • Serve as a trusted thought partner to the CMO and senior clinical leaders, helping prioritize initiatives and focus resources on high-impact opportunities.

Benefits

  • Paid vacation and sick time.
  • 401(k) match options and retirement savings options.
  • Health insurance, including medical, vision, and dental coverage.
  • Leadership development opportunities.
  • Continuing education stipends.
  • Flexible work environments.
  • Opportunities for high levels of responsibility and rapid advancement.
  • Wellness programs and other resources, based on eligibility.
  • CVS Health bonus, commission, or short-term incentive program eligibility.
  • Equity award target.
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