Sr. Director, IT Chief of Staff & Portfolio Management

Alignment Health is breaking the mold in conventional health care, committed to serving seniors and those who need it most: the chronically ill and frail. It takes an entire team of passionate and caring people, united in our mission to put the senior first. We have built a team of talented and experienced people who are passionate about transforming the lives of the seniors we serve. In this fast-growing company, you will find ample room for growth and innovation alongside the Alignment Health community. Working at Alignment Health provides an opportunity to do work that really matters, not only changing lives but saving them. Together.

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 / Responsibilities

• 1. 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 Responsibilities

Fulfill 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 Requirements

Experience

Required:

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

Education

Required:

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

Training

Required:

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 & Competencies

Technical / Role-Specific Skills

• 1. 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.

Licensure

Required:

None

Preferred:

Project Management Professional (PMP) — Project Management Institute

Certified Scrum Master (CSM), SAFe Program Consultant (SPC), or eq