The Director, Operations and Chief of Staff serves as a senior strategic operating partner and trusted advisor to the COO, enabling focused, aligned, and effective leadership across a complex, matrixed, highly regulated health insurance operations organization. This role translates COO priorities into disciplined operating rhythms, actionable plans, measurable outcomes, and sustained enterprise follow-through.
The Director partners with the COO's direct reports, senior leadership, finance, compliance, legal, IT, operational leaders, external partners, and enterprise stakeholders to accelerate decision-making, strengthen accountability, surface risks early, and advance strategic, regulatory, financial, operational, and transformation priorities across a 1,000+ employee operational organization.

Job Duties/Responsibilities:

Enterprise Operating Rhythm, Governance, and Executive Decision Support

• Lead the COO's enterprise operating cadence, including executive leadership meetings, operational reviews, business reviews, board preparation, leadership offsites, and cross-functional decision forums.
• Ensure senior leaders have the right information at the right time by developing agendas, briefing materials, executive presentations, decision documents, follow-up summaries, and action tracking tools.
• Translate COO priorities into structured plans with clear owners, milestones, measures, dependencies, timelines, and executive-level accountability.
• Serve as a senior extension of the COO by helping filter, prioritize, and route issues, requests, escalations, and opportunities based on urgency, risk, strategic value, and business impact.

Strategic Planning, Enterprise Execution, and Transformation Leadership

• Partner with the COO and senior leadership team to define, operationalize, and monitor strategic priorities aligned with enterprise goals, operational performance expectations, regulatory obligations, and transformation objectives.
• Lead annual, quarterly, and ad hoc operational planning processes, ensuring priorities are translated into practical roadmaps with clear outcomes and leadership ownership.
• Own or sponsor complex cross-functional initiatives spanning multiple business units or leadership domains, including operational efficiency, cost optimization, digital transformation, automation, vendor transitions, process redesign, and scalability efforts.
• Establish governance routines, executive reporting, risk escalation, stakeholder alignment, and milestone tracking to ensure enterprise-critical initiatives advance with urgency and discipline.

Operational Performance, Business Insights, Risk, and Regulatory Readiness

• Oversee executive-level dashboards, reporting frameworks, scorecards, and performance management routines that track key operational, financial, service, quality, compliance, and transformation metrics.
• Analyze performance across core health insurance operations, including claims, provider operations, customer service, enrollment and billing, utilization management, case management, compliance, IT enablement, and vendor operations.
• Synthesize trends, risks, dependencies, bottlenecks, and opportunities into concise, decision-grade recommendations for the COO and senior leadership.
• Partner with Compliance, Legal, Audit, Finance, IT, and operational leaders to monitor priorities related to CMS requirements, state regulatory requirements, HIPAA, privacy standards, operational controls, audit findings, and remediation commitments.

Executive Communications, Stakeholder Alignment, and Organizational Effectiveness

• Prepare the COO for executive leadership meetings, board discussions, regulatory or external engagements, vendor meetings, and high-stakes internal conversations by synthesizing context, anticipating questions, and developing briefing materials.
• Develop executive communications, strategic updates, leadership messages, board-level presentations, talking points, and analytical reports on behalf of the COO.
• Facilitate alignment across operational functions and enterprise stakeholders by establishing communication frameworks, relationship management systems, and meeting structures that support disciplined execution.
• Partner with Human Resources and senior leaders on organizational design, workforce planning, leadership effectiveness, succession planning, talent reviews, change readiness, and operating model improvements.

Supervisory Responsibilities

• Provides leadership, direction, coaching, prioritization, and accountability for assigned initiatives, workstreams, and matrixed contributors.

Job Requirements:

Experience - Required

• 10+ years of progressive experience in healthcare operations, health insurance, managed care, business operations, executive operations, strategic consulting, enterprise program management, transformation leadership, chief of staff, or a closely adjacent function.
• Demonstrated experience supporting C-suite or senior enterprise leaders in a fast-paced, complex, matrixed environment.
• Proven track record leading enterprise-level, cross-functional initiatives from strategy through execution with significant influence across senior stakeholders.
• Strong understanding of health insurance operations, including claims, customer service, provider operations, enrollment and billing, utilization management, case management, compliance, regulatory expectations, IT enablement, and vendor operations.
• Experience developing executive-level communications, business reviews, analytical materials, board-level presentations, decision documents, and recommendations for senior leadership.

Experience - Preferred

• Experience in Medicare Advantage, Medicaid, Commercial health plans, MSO, value-based care, or complex services organizations preferred.
• Prior experience supporting a COO, President, business unit leader, or enterprise operations executive preferred.
• Background in management consulting, business transformation, healthcare operations leadership, enterprise PMO, or large-scale operational transformation preferred.

Education

• Bachelor's degree in Business Administration, Finance, Healthcare Administration, Public Health, Operations, or a related field required; equivalent combination of education and relevant experience may be considered.
• MBA, MHA, MPH, or other relevant graduate degree preferred.

Training and Certifications

• Advanced proficiency with executive communication tools, including PowerPoint or presentation design tools, Excel, Teams, Outlook, SharePoint, dashboards, and collaboration platforms.
• Familiarity with project tracking, OKR frameworks, KPI dashboards, operating reviews, scorecards, or similar goal-management methodologies required.
• Project Management Professional, Lean Six Sigma, change management, process improvement, facilitation, or leadership development training preferred.

Specialized Skills and Key Competencies

• Executive Presence and Influence: Ability to engage credibly with senior leaders, operational executives, external partners, vendors, and enterprise stakeholders while representing the COO's office effectively.
• Strategic Analysis and Business Acumen: Ability to synthesize operational, financial, regulatory, and organizational information into decision-ready recommendations.
• Enterprise Execution Leadership: Demonstrated ability to lead complex initiatives across functions with disciplined tracking, risk management, accountability, and follow-through.
• Executive Communication: Exceptional written, verbal, and visual communication skills for executive briefings, board-level presentations, leadership messages, and strategic narratives.
• Healthcare Operations Acumen: Strong understanding of payer operations, managed care, service delivery, member and provider experience, regulatory obligations, and operational performance drivers.
• Organizational Navigation: Strong emotional intelligence, discretion, judgment, relationship-building, and ability to lead through influence in a matrixed environment.

Essential Physical Functions:

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

1. While performing the duties of this job, the employee is regularly required to talk or hear. The employee regularly is required to stand, walk, sit, use hand to finger, handle or feel objects, tools, or controls; and reach with hands and arms.

2. The employee frequently lifts and/or moves up to 10 pounds. Specific vision abilities required by this job include close vision and the ability to adjust focus.
Pay Range: $149,882.00 - $224,823.00
Pay range may be based on a number of factors including market location, education, responsibilities, experience, etc.