Head of Digital & Strategy

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Head of Digital & Strategy based in the United States.

This executive leadership role offers the opportunity to shape enterprise-wide digital transformation and establish a modern, product-driven operating model. You will lead strategic initiatives that align technology investments with long-term business objectives while driving innovation, operational excellence, and customer-focused digital experiences. Working closely with executive leadership and cross-functional teams, you will build scalable product management capabilities, oversee major transformation programs, and influence organizational strategy. This is an ideal opportunity for a visionary leader who excels at driving change, fostering collaboration, and delivering measurable business value within a complex, fast-paced environment.

• Establish and lead a high-performing Product Management organization, including governance frameworks, operating models, talent development, and best practices.
• Define and execute enterprise-wide digital and product strategies that align with long-term business objectives, customer needs, and organizational priorities.
• Develop strategic product roadmaps and portfolio prioritization frameworks that maximize business value and guide technology investments.
• Lead large-scale digital transformation and modernization initiatives, driving innovation, operational efficiency, and customer-centric solutions.
• Champion modern product management methodologies, including agile development, product lifecycle management, backlog prioritization, human-centered design, and data-driven decision-making.
• Partner closely with executive leadership, technology, operations, and business teams to ensure strategic alignment and successful execution of enterprise initiatives.
• Oversee launch and enablement activities to support successful deployment, organizational readiness, stakeholder engagement, and adoption of new products and digital capabilities.
• Serve as a trusted advisor to executive leadership by providing strategic recommendations on digital investments, product direction, organizational transformation, and business priorities.
• Present business cases, performance metrics, strategic initiatives, and transformation progress to executive stakeholders.
• Foster collaboration across multidisciplinary teams while driving continuous improvement, innovation, and scalable organizational growth.

Requirements:

• Bachelor's degree in Business Administration, Project Management, Information Systems, Technology Management, or a related field; equivalent experience may be considered.
• Minimum of 12 years of progressive leadership experience in Product Management, Digital Strategy, Business Transformation, or related disciplines.
• Proven success building, scaling, and leading Product Management organizations and product operating models.
• Demonstrated experience developing and executing enterprise product strategies aligned with business goals and customer outcomes.
• Extensive experience leading large-scale digital transformation, modernization, innovation, or enterprise change initiatives.
• Strong expertise in product roadmap development, portfolio management, prioritization frameworks, and cross-functional program delivery.
• Experience collaborating across business, technology, operations, and executive leadership within complex, matrixed organizations.
• Exceptional executive communication, stakeholder management, negotiation, and influencing skills.
• Strong strategic thinking, business acumen, and ability to align technology investments with organizational objectives.
• Experience presenting strategic recommendations, business cases, and performance insights to executive leadership.
• Preferred experience within healthcare, healthcare technology, Medicaid, managed care, or other highly regulated industries.
• Familiarity with ERP, CRM, payroll, claims administration, customer-facing digital platforms, Agile frameworks, Human-Centered Design, Product Operating Models, and Digital Transformation methodologies is highly desirable.

Benefits:

• Competitive annual salary ranging from $250,000 to $350,000, based on experience, qualifications, skills, and location.
• Executive-level leadership opportunity with significant strategic influence.
• Fully remote work environment with flexibility and executive collaboration.
• Opportunity to lead enterprise-wide digital transformation and innovation initiatives.
• Exposure to executive leadership and high-impact organizational decision-making.
• Collaborative culture focused on innovation, continuous improvement, and customer-centric solutions.
• Professional growth opportunities while shaping long-term business strategy and digital modernization.
• Comprehensive benefits package, including healthcare and additional employee programs (where applicable).