Executive Director, Business Transformation

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

At HCSC, our employees are the cornerstone of our business and the foundation to our success. We empower employees with curated development plans that foster growth and promote rewarding, fulfilling careers.

Join HCSC and be part of a purpose-driven company that will invest in your professional development.

This position is responsible for designing AI- and technology-enabled transformations that materially improve performance and position the enterprise for long-term success. This role is responsible for the full transformation lifecycle—from opportunity identification and operating model design through execution and sustained value realization. Operating as a trusted partner to Sr. Business and IT Leaders, the ED bridges strategy, business, and technology, ensuring transformation investments are tightly aligned to enterprise priorities and deliver measurable outcomes. The role also builds and leads a high-performing team of transformation and change management leaders and cultivates an innovation-led, execution-focused culture.

Job Responsibilities

Enterprise Transformation Leadership

• 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

AI & Technology-Enabled Change

• Identify, design, and scale AI-, data-, and technology-enabled solutions (including agentic and automation use cases) that fundamentally reshape how work gets done
• Partner closely with technology and business leaders to integrate digital and AI capabilities into core operating models

Value & Investment Management

• Shape and govern the transformation portfolio, ensuring investments are aligned to the enterprise strategy and deliver committed value
• Ensure compelling business cases, clear ROI, and rigorous benefit tracking across initiatives

Senior Executive Partnership

• Serve as a trusted thought partner to senior leaders, accelerating decisions, removing execution barriers, and aligning stakeholders across the enterprise
• Act as a connective tissue between corporate strategy, business units, and technology teams

People & Capability Building

• Build, lead, and develop a team of high-caliber transformation leaders
• Foster a culture of accountability, innovation, and continuous improvement

Required Job Qualifications

• Bachelor’s degree and 15 years professional work experience including experience at a top-tier consulting firm in strategy and/or large-scale Technology-enabled transformation roles or Advanced degree and 13 years professional work experience including experience at a top-tier consulting firm in strategy and/or large-scale Technology-enabled transformation roles
• 10 years’ Experience leading a team and other people leaders
• Senior leadership experience driving complex transformations within large, matrixed organizations
• Proven ability to lead cross-functional, enterprise-scale initiatives with measurable business impact
• Exceptional executive presence with a demonstrated ability to influence at the C-suite level

Preferred Job Qualifications

• Strong Technology and AI foundation, including experience with digital agents and agentic automation
• Healthcare, insurance, or highly regulated industry experience
• Track record of building and scaling transformation or innovation capabilities inside an enterprise

Compensation: $191,500.00 - $355,600.00

Exact compensation may vary based on skills, experience, and location

HCSC Employment Statement

We are an Equal Opportunity Employment employer dedicated to providing a welcoming environment where the unique differences of our employees are respected and valued. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, protected veteran status, or any other legally protected characteristics.

To learn more about available benefits, please click https://careers.hcsc.com/totalrewards