Senior Director Program Management

Simplify Recruiting; United States; Remote; USD 180,000 - 260,000; Full time

Job summary

Simplify Recruiting is seeking a Senior Director – Program Management to provide executive-level leadership across a portfolio of large health plan technology programs. This remote role oversees multiple workstreams spanning software engineering, data & integration, AWS/cloud, DevOps, and AI-enabled engineering.

You will own end-to-end delivery governance, lead Technical Program Managers and technology leaders across distributed teams, and serve as a Delivery Executive for VP and C-suite

Qualifications

• 18+ years of technology program/delivery management experience.
• 5+ years in senior delivery/program leadership managing large technology portfolios.
• Experience delivering large, complex software engineering programs.
• Consulting, professional services, health tech, or managed services experience.
• Strong understanding of AWS/cloud architecture and distributed systems.
• Experience leading large onshore/offshore delivery organizations.
• Executive-level client and stakeholder management experience.
• Strong knowledge of Agile, Scrum, SAFe, Kanban, and hybrid delivery methodologies.

Responsibilities

• Provide executive-level leadership across a portfolio of health plan technology programs.
• Own end-to-end delivery governance and integrated plans across multiple workstreams.
• Lead Technical Program Managers and technology leaders across distributed teams.
• Establish governance, delivery metrics, RAID management, dashboards, and dependency management.
• Govern Agile, SAFe, and hybrid delivery models; manage budgets and forecasts.
• Ensure HIPAA-aware delivery, security, quality, and client governance standards.
• Act as Delivery Executive for VP and C-suite client stakeholders; lead executive reviews.

Skills

Executive-level leadership

Program management

Stakeholder management

Agile/SAFe delivery

AWS/cloud architecture

Cross-functional leadership

Governance & metrics

AI-enabled delivery

HIPAA awareness

Tools

GitHub Copilot

Claude Code

Cursor

Job description

Domain: US Health Plan / Payer Technology (Currently working with Healthcare Payer Account)

Location: Remote – USA

Employment: Full-Time

Experience: 18+ years

About the Role

We are seeking a Senior Director – Program Management to provide executive-level leadership across a portfolio of complex health plan technology programs.

This is a senior, client-facing delivery leadership role at the intersection of technology, program execution, client engagement, and AI-first transformation.

You will own end-to-end delivery governance across multiple concurrent workstreams spanning software engineering, data & integration, AWS/cloud, DevOps, and AI-enabled engineering, while serving as a key point of accountability with senior client stakeholders and internal executive leadership.

What You’ll Lead

• Own end-to-end delivery across large, multi-team technology programs within the US health plan/payer domain.
• Lead Technical Program Managers and Technology Leaders across distributed onshore/offshore teams.
• Establish program governance, integrated plans, delivery metrics, RAID management, executive dashboards, and dependency management.
• Govern Agile, SAFe, and hybrid delivery models.
• Manage program budgets, forecasts, resource plans, and cost-to-complete.
• Ensure HIPAA-aware delivery, security, quality, and client governance standards.
• Serve as a Delivery Executive for VP and C-suite client stakeholders.
• Lead executive steering committees, QBRs, delivery reviews, and critical escalations.
• Partner with engineering and architecture leadership across AWS, distributed systems, data engineering, integration, and DevOps.
• Champion AI-assisted engineering, testing, documentation, operations, and program delivery.
• Establish measurable AI adoption and productivity goals across programs.
• Bring practical familiarity with GitHub Copilot, Claude Code, Cursor, or similar AI tools.
• Understand RAG, embeddings, prompt engineering, agentic workflows, and responsible AI.
• Establish AI governance appropriate for regulated healthcare environments, including protection of PHI and sensitive client/member data.
• Identify AI-driven automation opportunities throughout the delivery lifecycle.

What We’re Looking For

• 18+ years of technology program/delivery management experience.
• 5+ years in senior delivery/program leadership managing large technology portfolios.
• Experience delivering large, complex software engineering programs.
• Consulting, professional services, health tech, or managed services experience.
• Strong understanding of AWS/cloud architecture and distributed systems.
• Experience leading large onshore/offshore delivery organizations.
• Executive-level client and stakeholder management experience.
• Strong knowledge of Agile, Scrum, SAFe, Kanban, and hybrid delivery methodologies.