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Careers at Castlight Health
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Senior Director, Strategy & Operations

$156,400 - $217,000/year
23 Oct 2025
California, USA
Verified by Turrior

Content + Source + Freshness • 12 Dec 2025 • 95% confidence

88 / 100

Offer value

High value due to leadership role in a reputable healthcare organization, competitive salary, and opportunities for strategic influence.

  • Competitive salary: $156,400 – $217,000/year
  • Influence major strategic decisions in a healthcare company
  • Work in a reputable organization focused on healthcare improvement
  • Extensive experience required (10+ years)
Pros
  • Competitive annual salary range of $156,400 – $217,000 plus bonuses
  • Leadership role with significant influence on healthcare strategy and operations
  • Comprehensive wellness programs and a commitment to employee development
Cons
  • High expectations could lead to a demanding work environment
  • Requires extensive experience (10+ years) which may limit candidate pool
  • Involves navigating complex regulatory compliance issues

Who it's for

Senior / Executive • Hybrid / Remote options may be available

Good fit
  • Experienced healthcare executives
  • Those passionate about healthcare innovation
  • Candidates with strong strategic planning skills
Not recommended for
  • Individuals with limited experience in healthcare strategy
  • Candidates who prefer strict operational roles
  • Job seekers with an interest in entry-level positions

Motivation fit

Desire to lead strategic initiatives in healthcareInterest in working in a fast-paced, impact-driven environmentCommitment to improving healthcare quality and efficiency

Key skills

Strategic planningRegulatory complianceData analyticsCross-functional collaborationLeadership and mentorship
Score: 88/100 AI verified analysis

About the job

Job Description Summary

The Senior Director, Strategy & Operations will be responsible for driving enterprise-wide strategic planning, operational excellence, and critical initiatives for CareMore Health. This leader will play a central role in aligning clinical, administrative, and shared services functions with business objectives, ensuring scalable growth and performance optimization across Medicare and Medicaid populations.

How will you make an impact & Requirements

Enterprise Strategy & Operations

    • Lead the annual and multi-year strategic planning process, aligning with enterprise objectives and investor expectations.

    • Serve as a strategic advisor to the VP, Strategy & Operations and executive leadership, preparing board-level updates and enterprise communication materials.

    • Manage cross-functional strategic initiatives such as new care model design, integration of acquired assets, and technology-enabled transformation.

    • Drive operational excellence by partnering with leaders across Care Management, Utilization Management, Pharmacy, and Provider Networks to improve quality, efficiency, and financial outcomes.

Data Strategy & Analytics Leadership

    • Spearhead enterprise-wide data strategy, ensuring analytics initiatives align with both clinical and administrative business objectives.

    • Design and implement scalable architecture and governance frameworks that improve data quality, accessibility, and standardization across all business units.

    • Partner with executive leadership to define KPIs and decision frameworks, enabling faster, insight-driven strategic planning.

    • Oversee enterprise performance dashboards and metrics to measure progress against strategic and operational priorities.

Cross-Functional Collaboration

    • Drive collaboration between clinical teams, shared services, and administrative functions to align priorities and ensure consistent execution.

    • Foster a culture of accountability, transparency, and data-driven decision-making across the enterprise.

    • Lead and mentor a team of strategy, operations, and analytics professionals.

Regulatory & Compliance Alignment

    • Ensure all activities comply with CMS, NCQA, and other applicable regulatory and accreditation standards.

    • Maintain strong governance practices that balance regulatory requirements with innovation and operational agility.

Qualifications

  • Bachelor’s degree in healthcare administration, business, economics, data science, or related field required; Master’s degree (MBA, MHA, MPH, or MS in Analytics/Health Informatics) strongly preferred.

  • 10+ years of progressively responsible experience in healthcare strategy, operations, or analytics within payer, provider, or value-based care organizations.

  • Proven track record of leading enterprise-level data strategy and governance frameworks in healthcare.

  • Strong knowledge of CMS regulations, Medicare/Medicaid programs, and value-based care models.

  • Exceptional leadership, communication, and executive presence; able to influence board and senior executives.

  • Demonstrated ability to thrive in a private equity-owned or fast-growth healthcare environment.

Compensation: $156,400K - $217,000K & bonus eligible

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