Head of Digital & Strategy

Location: Remote (Executive Leadership Presence Preferred)
Department: Digital Transformation & Strategy
Reports To: Chief Executive Officer (CEO) &  President

GT Independence is seeking an experienced and visionary Head of Digital & Strategy to lead our evolution into a product-driven organization. This executive leadership role will establish and scale a modern Product Management function, align digital investments with strategic business priorities, and drive enterprise-wide transformation initiatives that deliver meaningful value to our customers, employees, and stakeholders.

As a strategic advisor to the CEO and executive leadership team, you will help shape the future of GT Independence by creating the frameworks, governance, and operating models necessary to deliver innovative, scalable, and customer-centric digital solutions across a complex, multi-state healthcare services environment.

The Head of Digital & Strategy leads GT Independence’s continued transformation toward a product-driven organization, establishing best-in-class product management practices while ensuring technology investments align with long-term business objectives.

This leader will develop and mature GTI’s product management capabilities, create scalable processes for prioritization and execution, and drive alignment across business, technology, and operational teams. The role will oversee the strategic planning, development, launch, and adoption of key digital initiatives that support organizational growth and operational excellence.

• Establish and lead a world-class Product Management function, including organizational structure, governance, operating models, and talent development.
• Define and evolve enterprise product strategy aligned with GTI’s business goals, customer needs, and long-term growth objectives.
• Develop and maintain product roadmaps that drive measurable business outcomes.
• Build prioritization frameworks that ensure strategic initiatives receive appropriate focus and investment.

• Lead enterprise-wide digital modernization and transformation initiatives.
• Drive the adoption of modern product management methodologies, including:
  • Product lifecycle management
  • Agile product development
  • Backlog management
  • Customer-centric design principles
  • Data-driven decision making
• Ensure digital initiatives deliver measurable value and support GTI’s operational and strategic objectives.

• Partner closely with executive leadership, technology teams, operations, and business stakeholders to align product development with business priorities.
• Foster strong collaboration across Product, Engineering, Operations, and Business teams to support coordinated execution and scalable delivery.
• Guide cross-functional teams through complex organizational initiatives and transformational change.

• Lead and support the Launch & Enablement function to ensure successful deployment and adoption of new products, platforms, and enhancements.
• Establish processes that promote organizational readiness, stakeholder engagement, and effective change management.

• Serve as a trusted strategic advisor to the CEO and Executive Leadership Team.
• Provide recommendations regarding product direction, technology investment priorities, and organizational transformation opportunities.
• Present business cases, strategic initiatives, and performance metrics to executive stakeholders.

• Bachelor’s degree in Business Administration, Project Management, Information Systems, Technology Management, or a related field.
• Equivalent combination of education and a minimum of 12 years of relevant experience will be considered.

• 12+ years of progressive leadership experience in Product Management, Digital Strategy, Business Transformation, or related disciplines.
• Proven success building and leading Product Management organizations and operating models.
• Experience developing and executing enterprise product strategies aligned with business goals.
• Demonstrated success leading large-scale digital transformation, modernization, or innovation initiatives.
• Strong expertise in roadmap development, portfolio prioritization, and delivery of complex cross-functional programs.
• Experience working across business, operations, and technology functions within matrixed environments.
• Exceptional communication, executive presence, and stakeholder management skills.
• Proven ability to influence senior leaders and drive alignment across diverse teams.

• Experience within healthcare, healthcare technology, Medicaid, managed care, or related regulated industries.
• Knowledge of enterprise platforms such as ERP, claims administration, payroll, tax, CRM, or customer-facing digital systems.
• Experience operating in multi-state, highly regulated, or complex service-delivery environments.
• Familiarity with Human-Centered Design, Agile frameworks, Product Operating Models, and Digital Transformation methodologies.

In this role, you will:

• Establish a scalable Product Management organization that drives innovation and business value.
• Create enterprise-wide prioritization and governance frameworks for digital initiatives.
• Improve alignment between strategic objectives and technology investments.
• Accelerate the delivery of customer-focused digital solutions.
• Strengthen collaboration across business, operations, and technology teams.
• Drive measurable improvements in organizational performance, efficiency, and customer experience.

At GT Independence, our mission is to support people who choose self-direction as their path to independence. You will have the unique opportunity to influence enterprise strategy, lead transformational initiatives, and shape the future of digital innovation within a growing organization dedicated to making a meaningful impact in the communities we serve.

Join us and help define the next chapter of GT Independence's digital transformation journey.

Apply today.