Head of Digital & Strategy

GT Independence

$130K — $180K *
US-AnywhereRemote in United States
Healthcare
11 - 15 years of experience
Job Overview by Ladders

Qualifications

  • 12+ years of leadership experience in Product Management or Digital Strategy.
  • Proven track record in building and managing Product Management organizations.
  • Experience in developing enterprise product strategies that align with business goals.
  • Demonstrated success in executing large-scale digital transformation initiatives.
  • Strong expertise in roadmap development and portfolio prioritization.
  • Ability to influence senior leaders and align diverse teams across functions.
  • Exceptional communication and stakeholder management skills.

Responsibilities

  • Establish a world-class Product Management function including structure and governance.
  • Define and evolve product strategy aligned with business growth goals.
  • Develop product roadmaps that drive measurable outcomes.
  • Build prioritization frameworks for strategic initiatives.
  • Lead enterprise-wide digital transformation initiatives.
  • Promote modern product management methodologies and practices.
  • Guide cross-functional teams through complex organizational change.

Benefits

  • Remote work flexibility; Executive leadership presence preferred.
  • Opportunity to lead and make a significant impact in digital transformation.
  • Access to professional development and training.
  • Collaborative work environment with executive mentorship.
  • Potential for influencing the organization's strategic direction.
Full Job Description
Location: Remote (Executive Leadership Presence Preferred)
Department: Digital Transformation & Strategy
Reports To: Chief Executive Officer (CEO) & President

Position Summary

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.

Key Responsibilities

Product Strategy & Leadership

  • 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.

Digital Transformation & Innovation

  • 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.

Cross-Functional Leadership

  • 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.

Launch & Enablement Oversight

  • 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.

Executive Partnership

  • 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.

Required Education

  • 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.

Qualifications & Experience

Required

  • 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.

Preferred

  • 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.

What Success Looks Like

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.

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