Executive Director, Enterprise Transformation & AI

Health Care Service Corporation; Chicago (IL); On-site; USD 192,000 - 356,000; Full time

Job summary

Health Care Service Corporation is seeking an Enterprise Transformation Leader to drive AI- and technology-enabled transformations across the organization from opportunity to value realization. You will partner with senior executives to align investments with enterprise priorities and lead a high-performing transformation team.

The role requires 15+ years in strategy or large-scale technology-enabled transformations, with strong executive presence and cross-functional leadership.

Qualifications

• Bachelor’s degree with extensive strategy and large-scale technology-enabled transformation experience.
• 10+ years leading teams and people leaders; executive-level influence.
• Senior leadership experience delivering enterprise-scale transformations in matrixed organizations.
• Proven ability to drive cross-functional initiatives with measurable business impact.
• Strong understanding of AI, data, and technology-enabled change.

Responsibilities

• Drive end-to-end execution of enterprise-wide transformation initiatives, including opportunity identification, prioritization, business case development, delivery, and value realization.
• Translate strategic priorities into actionable transformation roadmaps with clear financial and operational outcomes.
• Identify, design, and scale AI-, data-, and technology-enabled solutions that reshape how work gets done.
• Partner with technology and business leaders to integrate digital and AI capabilities into core operating models.
• Shape and govern the transformation portfolio, ensuring investments align to enterprise strategy and deliver value.
• Serve as a trusted thought partner to senior leaders, aligning stakeholders across the enterprise.
• Build, lead, and develop a team of transformation leaders; foster accountability and continuous improvement.
• Act as connective tissue between corporate strategy, business units, and technology teams.
• Ensure compelling business cases with ROI and rigorous benefit tracking.

Skills

Team leadership

Executive presence

Cross-functional leadership

Strategic leadership

AI foundation

Education

Bachelor’s degree

Advanced degree

Job description

Health Care Service Corporation is seeking an Enterprise Transformation Leader to drive AI- and technology-enabled transformations across the organization from opportunity to value realization. You will partner with senior executives to align investments with enterprise priorities and lead a high-performing transformation team.

The role requires 15+ years in strategy or large-scale technology-enabled transformations, with strong executive presence and cross-functional leadership.