Director Digital Delivery

Director, Digital Delivery

The Director, Digital Delivery provides enterprise leadership in translating business strategy into scalable, measurable digital outcomes across the health plan. This role owns the strategy, roadmap, delivery, performance, and continuous evolution of customer-facing digital platforms (Web and Mobile), ensuring investments deliver differentiated customer experiences, operational efficiency, compliance, and measurable business value. This role drives digital transformation through an AI-first approach, embedding generative, agentic, and predictive AI across customer experiences, operational workflows, and the product lifecycle, while scaling AI-assisted engineering to improve velocity, quality, and speed-to-market.

The Director oversees cross-functional digital capabilities, including product management, UX, engineering, testing, architecture, and operations, ensuring teams operate with modern, cloud-native, and AI-enabled delivery practices. This role also champions a culture of innovation, experimentation, and continuous improvement while ensuring strong governance, financial discipline, and regulatory compliance in a healthcare environment.

Essential Accountabilities

• Partners with senior leadership to translate enterprise strategy into a multi-year digital roadmap and delivery plan aligned to customer needs, business priorities, and measurable outcomes.
• Owns the end-to-end strategy, lifecycle, performance, reliability, and continuous evolution of customer-facing Web and Mobile platforms, ensuring a secure, scalable, and high-performing digital ecosystem.
• Leads the integration of generative, agentic, and predictive AI across digital experiences, personalization, self-service, and operational workflows, while scaling AI-assisted engineering to accelerate innovation and delivery speed.
• Accountable for end-to-end digital delivery across scope, timeline, budget, quality, and compliance, advancing Agile, Dev Ops, CI/CD, API-first, and cloud-native practices across Azure and AWS environments.
• Leads and develops cross-functional teams spanning product, UX, engineering, testing, and architecture; builds organizational capability through AI-assisted engineering practices, upskilling, and adoption of best-in-class delivery standards.
• Establishes KPIs and leverages analytics, experimentation (A/B testing), and AI-driven insights to optimize customer experience, platform performance, and business outcomes.
• Oversees digital financials, vendor partnerships, and investment prioritization while establishing governance frameworks, responsible AI guardrails, and compliance with healthcare regulations, privacy, security, and audit requirements.
• Consistently demonstrates high standards of integrity by supporting the Lifetime Healthcare Companies' mission and values, adhering to the Corporate Code of Conduct, and leading to the Lifetime Way values and beliefs.
• Models the Lifetime Way behaviors and values on a consistent basis and promotes these behaviors across the organization while developing high-performing leaders and teams.
• Maintains knowledge of all relevant legislative and regulatory mandates and ensures that all activities are compliant with these requirements.
• Regular reliable attendance is expected and required.
• Maintains high regard for member privacy in accordance with the corporate privacy policies and procedures.
• Performs other functions assigned by management.

Minimum Qualifications

• Ten (10) years of related experience in digital products, technology delivery in regulated industries, of which three (3) years of defined leadership experience managing across the digital technology function.
• Bachelor's degree in technology, business or related field. In lieu of a degree, six (6) years of experience required.
• Demonstrated expert experience leading digital product and technology delivery within a healthcare payer environment, including member-facing platforms, regulatory compliance requirements, and industry standards (e.g., HIPAA, CMS).
• Demonstrated advanced experience driving AI-enabled transformation and cloud platform modernization initiatives, including scaling AI-assisted software…