The Senior Director, Chief of Staff & Portfolio Management serves as the strategic operating partner to the Chief Digital Officer, translating digital vision into disciplined execution across a complex Medicare Advantage technology and operations portfolio. This role works directly with the CDO, executive leadership team, clinical, finance, compliance, and operational stakeholders to align priorities, govern investments, and drive outcomes across the organization's most critical digital programs. The role owns the Technology portfolio program management function - including project management, performance reporting, and initiative execution - and serves as the senior accountability point for organizational operating rhythms and cross-functional program delivery. Success is measured by the health and pace of technology initiatives, quality of executive decision-making support, and the maturity of portfolio governance practices across the Technology function.
Job Duties / Responsibilities1. Advise and Enable CDO Decision-Making.
Partner with the CDO as a primary strategic thought partner - synthesizing data, preparing executive communications, and coordinating leadership priorities to accelerate informed decisions.
2. Lead Technology Portfolio Governance.
Own the portfolio management function, including initiative intake, prioritization, governance frameworks, and status reporting, to ensure investments stay aligned with technology and organizational strategy.
3. Drive Cross-Functional Program Execution.
Direct the execution of complex, cross-functional initiatives spanning technology, clinical operations, regulatory compliance, and business functions, resolving blockers and maintaining delivery momentum.
4. Govern Technology Investment & Capital Planning.
Manage the annual and multi-year technology investment planning process in partnership with Technology, Finance, and business leaders, while building tooling and processes to track spend performance, value realization, and build-versus-buy decisions.
5. Establish and Drive Operating Rhythms.
Build and maintain the CDO organization's operating cadences - leadership meetings, governance forums, planning cycles - fostering accountability, transparency, and continuous improvement.
6. Deliver Executive Performance Reporting.
Develop and manage scorecards, KPIs, and operational dashboards that provide the CDO, CEO, and Board Committees with timely visibility into portfolio health, risks, and decision requirements.
7. Lead Organizational Effectiveness Initiatives.
Support operating model adoption, transformation programs, and execution maturity improvements that strengthen how the digital organization delivers at scale in a Medicare Advantage regulated environment.
Supervisory ResponsibilitiesFulfill supervisory responsibilities in accordance with organization policies and applicable laws. Responsibilities include interviewing, hiring, and training employees; planning, assigning, and directing work; appraising performance; rewarding and disciplining employees; addressing complaints and resolving problems.
Job RequirementsExperienceRequired:
- 8-12 years of progressive experience in digital strategy, program management, technology portfolio governance, or a related strategic operations function
- 3+ years of experience in a healthcare payer, managed care, or Medicare Advantage environment, with demonstrated understanding of CMS regulatory requirements, HIPAA compliance, and health plan operations
- Demonstrated experience leading and governing complex, cross-functional technology or digital portfolios with measurable outcomes
- Proven track record as a strategic advisor or operating partner to C-suite or senior executive leaders, including preparation of board-level communications and executive decision support
- Experience establishing and operationalizing PMO governance frameworks, portfolio management methodologies, and organizational operating cadences
Preferred:
- Prior experience in a Chief of Staff, Strategy & Operations Director, or Senior Program Director role supporting a CDO, CTO, or equivalent digital executive in a health insurance or health technology organization
- Experience leading operating model transformation or product-centric organizational adoption in a regulated healthcare environment
- Background in Lean, Six Sigma, or equivalent process improvement and operational excellence disciplines
EducationRequired:
- Bachelor's degree in Business Administration, Information Technology, Healthcare Administration, Health Informatics, or a related field; 4 years of additional relevant experience may be considered in lieu of a degree
Preferred:
- Master's degree (MBA, MHA, MIS, or equivalent) with a focus on strategy, operations, or healthcare management
TrainingRequired:
- Familiarity with structured program and project management methodologies (e.g., PMI/PMP, Agile, SAFe, or equivalent); formal training or applied experience is acceptable
- Working knowledge of HIPAA compliance requirements and CMS regulatory frameworks applicable to Medicare Advantage plan operations
Preferred:
- Project Management Professional (PMP) certification or equivalent portfolio/program management credential
- Agile or SAFe certification (e.g., SAFe Program Consultant, Certified Scrum Master) where applicable to the delivery model
- Training in healthcare IT governance, operational frameworks, or value-based care management
Skills & CompetenciesTechnical / Role-Specific Skills1. Portfolio & Program Governance
Ability to design and operate governance structures, manage multi-initiative portfolios, and ensure strategic alignment, investment discipline, and delivery accountability at scale.
2. Executive Communication & Stakeholder Influence
Proven ability to build board-ready materials, translate complex technology portfolios into business narratives, and influence senior leaders across technology, clinical, finance, and compliance functions.
3. Digital Strategy & Operating Model Design
Deep understanding of digital transformation principles, product-centric operating models, and the organizational changes required to sustain them in a regulated Medicare Advantage environment.
4. Medicare Advantage / Healthcare Payer Domain Knowledge
Working knowledge of Medicare Advantage plan operations, CMS regulations, Stars programs, risk adjustment, and HIPAA compliance as they relate to digital and technology initiatives.
5. Performance Measurement & Executive Reporting
Ability to build and maintain scorecards, KPIs, and dashboards that provide actionable visibility into portfolio health, organizational risk, and strategic initiative performance.
6. Cross-Functional Program Execution
Demonstrated ability to orchestrate delivery across vendor partners, product teams, engineering, clinical operations, and business units in a complex, matrixed organization.
7. AI & Digital Health Awareness
Familiarity with AI/ML use cases applicable to healthcare operations and ability to incorporate digital innovation priorities into portfolio planning and governance processes.
LicensureRequired:
Preferred:
- Project Management Professional (PMP) - Project Management Institute
- Certified Scrum Master (CSM), SAFe Program Consultant (SPC), or equivalent Agile delivery credential
Essential Physical FunctionsThe 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 accommodation may be made to enable individuals with disabilities to perform the essential functions.
- 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.
- 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: $172,364.00 - $258,547.00
Pay range may be based on a number of factors including market location, education, responsibilities, experience, etc.
