Director, Operating Effectiveness Principal

Cigna Healthcare

$125K — $150K *
Healthcare
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor's degree
  • 10+ years in consulting, strategy, program management, or related leadership roles
  • Experience with executive-level support and leadership teams
  • Proven track record in complex organizational transformations
  • Strong skills in executive communications and presentations

Responsibilities

  • Develop change strategy and manage stakeholder engagement
  • Create and implement adoption plans for transformation initiatives
  • Lead organizational change and assess readiness
  • Design and execute engagement programs and executive communications
  • Facilitate town halls and establish feedback mechanisms
  • Provide leadership coaching to enhance team performance
  • Oversee strategic planning and leadership team governance

Benefits

  • Flexible work options including occasional remote work
  • Internet connection requirements for remote setup
  • Opportunities for professional development through exposure to high-level executives and transformative projects
Full Job Description
We are seeking a Director of Organizational Effectiveness to serve as a trusted strategic partner to the Vice President of Product and Delivery. This role combines chief of staff leadership, organizational transformation, change management, executive communications, and employee engagement to help drive alignment, execution, and organizational performance across a complex technology organization.

The ideal candidate is a highly influential leader who excels through collaboration rather than formal authority, effectively navigating ambiguity while turning strategy into measurable business outcomes.

Key Responsibilities:

Organizational Transformation & Change
  • Change strategy
  • Stakeholder management
  • Adoption planning
  • Transformation leadership
  • Readiness assessments


Culture, Engagement & Leadership Enablement
  • Engagement programs
  • Executive communications
  • Town halls
  • Feedback mechanisms
  • Leadership coaching


Strategic Operations & Chief of Staff
  • Strategic planning
  • Leadership team governance
  • Executive communications
  • Action tracking
  • Business reviews


Minimum Qualifications:
  • Bachelor's degree required
  • 10+ years of experience in consulting, strategy, program management, organizational effectiveness, change management, chief of staff, or related leadership roles.
  • Experience supporting executive-level leaders and leadership teams.
  • Proven success leading complex organizational transformations and enterprise initiatives.
  • Strong experience developing executive communications and presentations.


Additional Desired Qualifications
  • Experience within healthcare, technology, operations, or highly matrixed organizations.
  • Formal change management certification (Prosci, CCMP, or equivalent).
  • Experience supporting large-scale organizational redesign, mergers, integrations, or transformation programs.
  • Exceptional executive presence and written communication skills.
  • Strong facilitation and stakeholder management capabilities.
  • Experience navigating ambiguity and competing priorities.
  • Proven ability to build trusted relationships across all organizational levels


If you will be working at home occasionally or permanently, the internet connection must be obtained through a cable broadband or fiber optic internet service provider with speeds of at least 10Mbps download/5Mbps upload.

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