Head of Digital & Strategy

Accountabilities: 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).