Head of Digital & Strategy

About the Role

This executive leadership position is based in the United States, aiming to drive enterprise-wide digital transformation and establish a modern, product-focused operational framework. The Head of Digital & Strategy will guide strategic initiatives to synchronize technology assets with long-term business goals, fostering innovation, operational excellence, and enhanced digital customer experiences. Collaborating with senior executives and cross-disciplinary teams, the role involves building scalable product management practices, steering key transformation programs, and influencing organizational direction in a dynamic environment.

Key Responsibilities

• Lead a high-performance Product Management team by implementing governance models, operational frameworks, talent cultivation, and industry best practices.
• Craft and implement comprehensive digital and product strategies aligned with business aims, customer expectations, and company priorities.
• Design strategic product roadmaps and apply portfolio prioritization techniques that optimize business value and guide technology spending.
• Oversee large digital modernization efforts, encouraging innovation, operational efficiency, and customer-centric product solutions.
• Advocate for advanced product management approaches including agile methodologies, product lifecycle oversight, backlog management, human-centered design, and decisions driven by data analytics.
• Work closely with executive leadership, IT, operations, and business units to guarantee alignment and successful delivery of significant enterprise projects.
• Manage product launches and organizational enablement to ensure readiness, engagement of stakeholders, and adoption of new digital tools and capabilities.
• Act as a strategic advisor to top executives by delivering insight on digital investments, product direction, organizational changes, and business priorities.
• Communicate business cases, performance indicators, strategic projects, and progress reports to executive stakeholders.
• Promote collaboration among diverse teams while encouraging continuous innovation and scalable organizational growth.

Required Qualifications and Experience

• A Bachelor’s degree in Business Administration, Project Management, Information Systems, Technology Management, or a related discipline; equivalent professional experience is considered.
• At least 12 years of progressive leadership experience in Product Management, Digital Strategy, or Business Transformation roles.
• Proven track record of building, expanding, and leading Product Management functions and operational models.
• Demonstrable experience in establishing and executing enterprise-level product strategies aligned with business outcomes and customer satisfaction.
• Substantial expertise in leading extensive digital transformation, modernization projects, and enterprise-wide innovative initiatives.
• Strong capabilities in product roadmap creation, portfolio oversight, prioritization methodologies, and cross-functional program leadership.
• Experience navigating complex matrixed organizations through collaboration with business, technology, operations, and senior leadership.
• Exceptional communication, stakeholder engagement, negotiation, and influencing skills at the executive level.
• Strategic mindset combined with business insight to align technology investments with corporate objectives.
• Experience preparing and delivering strategic recommendations, business cases, and performance data to executive teams.
• Preferred background includes healthcare, healthcare technology, Medicaid, managed care, or comparable regulated sectors.
• Familiarity with ERP, CRM, payroll systems, claims administration, customer-facing digital platforms, Agile frameworks, Human-Centered Design, and digital transformation practices is highly advantageous.

Compensation and Benefits

• A competitive annual salary ranging from 250000 to 350000 USD, depending on experience, qualifications, skills, and location.
• Leadership role at the executive level with substantial influence over strategic initiatives.
• Fully remote work setup providing flexibility and collaboration with senior leadership.
• Opportunity to spearhead large-scale digital transformation and innovation programs.
• Direct exposure to organizational leadership and impactful decision-making processes.
• A culture fostering innovation, ongoing enhancement, and customer-focused solutions.
• Opportunities for professional advancement while shaping strategic business direction and digital modernization.
• Comprehensive benefits including healthcare and relevant employee programs where applicable.

Additional Information

The recruitment process involves an AI-driven candidate matching system that objectively reviews applications against core role requirements. Top candidates are forwarded directly to the hiring organization, which manages further selection steps such as interviews and assessments. Applicants should note data privacy policies complying with applicable regulations and the use of AI tools supporting the hiring process, although final decisions rest with human evaluators.