Executive Director Business Transformation

HCSC; Chicago (IL); On-site; USD 192,000 - 356,000; Full time

Job summary

Health Care Service Corporation (HCSC) in Chicago, IL, is seeking an Enterprise Transformation Leader to design and drive AI- and technology-enabled transformations across the full lifecycle, from opportunity identification to value realization, in collaboration with senior business and IT leaders.

You will build and guide a high-performing transformation team, govern the portfolio, secure ROI, and ensure initiatives align to enterprise priorities while shaping the organization’s strategy and

Qualifications

• Bachelor’s degree and 15 years professional work experience in strategy or large-scale technology-enabled transformations, or an advanced degree with 13 years of experience.
• 10 years’ experience leading a team and people leaders.
• Senior leadership experience driving complex transformations in large, matrixed organizations.
• Proven ability to lead cross-functional, enterprise-scale initiatives with measurable business impact.
• Exceptional executive presence with ability to influence at the C-suite level.

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 deliver value and ROI.
• Serve as a trusted thought partner to senior leaders and align stakeholders across the enterprise.
• Build, lead, and develop a team of transformation leaders; foster accountability and innovation.

Skills

Executive leadership

Cross-functional leadership

Strategic transformation

C-suite influence

People leadership

Education

Bachelor’s degree with 15 years experience

Advanced degree with 13 years experience

Job description

Flex

IL - Chicago

Full time

R0049375

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.

Job Summary

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

Pay Transparency Statement:

At Health Care Service Corporation, you will be part of an organization committed to offering meaningful benefits to our employees to support their life outside of work. From health and wellness benefits, 401(k) savings plan, pension plan, paid time off, paid parental leave, disability insurance, supplemental life insurance, employee assistance program, paid holidays, tuition reimbursement, plus other incentives, we offer a robust total rewards package for employees. Learn more about our benefit offerings by visiting https://careers.hcsc.com/totalrewards.

The compensation offered will vary depending on your job-related skills, education, knowledge, and experience. This role aligns with an annual incentive bonus plan subject to the terms and the conditions of the plan.

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.

Base Pay Range

$191,500.00 - $355,600.00

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

For more than 80 years, HCSC has been dedicated to expanding access to high-quality, cost-effective health care and equipping our members with information and tools to make the best health care decisions for themselves and their families. As an industry leader, HCSC also has been helping to make the health care system work better for all Americans. To remain a leader, we offer compelling careers that encourage resourcefulness, strategic thought and empower you to make a difference in the lives of our members and their communities.

Today, with the industry at an important crossroad, HCSC is reimagining health care and looking for original thinkers who aren’t afraid to make innovative contributions. We are an Equal Opportunity Employment employer dedicated to workforce diversity and a drug-free and smoke-free workplace. Learn more about HCSC, our commitment to our members and the opportunity you’ll have to improve health care delivery in an open, collaborative environment.

HCSC is committed to diversity in the workplace and to providing equal opportunity to employees and applicants.

If you are an individual with a disability or a disabled veteran and need an accommodation or assistance in either using the Careers website or completing the application process, you can call us at 1-866-977-7378 to request reasonable accommodations.

Please note that only requests for accommodations in the application process will be returned. All applications, including resumes, must be submitted through HCSC's Career website on-line application process. If you have general questions regarding the status of an existing application, navigate to "candidate home" to view your job submissions.

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