[Hiring] Director of Sales AI Transformation @UnitedHealth Group

Role Description

The Director, AI Transformation, Medicare Sales Digital & Technology Experience will lead the transformation and delivery of a core suite of established and emerging AI products across the Medicare shopping and sales ecosystem. The role will connect experiences serving consumers, field agents, external distribution partners, internal telesales representatives, and Producer Help Desk teams into a cohesive, intelligent product portfolio.

This leader will shape how AI capabilities share trusted knowledge, apply persona-specific context and skills, preserve journey state, and support seamless transitions from one channel or tool to another. The goal is a simpler shopping experience that reduces repeated work, accelerates answers, improves consistency, and enables timely next-best-action recommendations while retaining appropriate human judgment and control.

This is not an innovation lab role. It is an enterprise product transformation and delivery role accountable for moving a portfolio of AI-enabled experiences from fragmented capabilities toward a unified, scalable operating model. The successful candidate will combine modern digital product leadership, technical fluency, engineering partnership, and user-first experience judgment with a bias toward shipping, measurement, and continuous improvement.

You’ll enjoy the flexibility to work remotely from anywhere within the U.S. as you take on some tough challenges.

Qualifications

• Bachelor's degree or equivalent practical experience
• 5+ years of demonstrated experience in artificial intelligence (AI), machine learning, generative AI, AI agents, or related technologies
• Demonstrated success transforming a digital product organization or complex product portfolio within a modern, technology-enabled company
• Experience leading multiple customer-facing and employee-facing digital products through strategy, delivery, adoption, optimization, and lifecycle decisions
• Proven ability to connect product experience, platform architecture, data, AI, and engineering delivery into a cohesive roadmap
• Solid technical fluency with modern software delivery, APIs, cloud platforms, data products, AI architectures, product telemetry, experimentation, and quality practices
• Working knowledge of conversational AI and voice experience concepts
• Hands-on familiarity with AI-assisted development tools and agentic engineering workflows
• Experience leading cross-functional product, design, engineering, data, and operations teams in a large, matrixed environment
• Exceptional ability to simplify complexity, make decisions with incomplete information, and communicate clearly with executives and delivery teams
• Demonstrated user-first product judgment, delivery discipline, and success improving speed without sacrificing quality or trust

Requirements

• 10+ years of experience in digital product management, software product development, technology transformation, platform leadership, or related roles
• Experience in healthcare, Medicare, insurance, financial services, travel, retail, or another complex and highly regulated consumer industry
• Experience modernizing digital shopping, marketplace, commerce, customer service, contact center, CRM, or sales enablement ecosystems
• Experience building multi-persona platforms that adapt context, permissions, workflows, and recommendations by user type
• Experience with conversational AI, retrieval-augmented generation, agentic workflows, shared knowledge platforms, recommendation systems, or next-best-action capabilities
• Experience designing seamless digital-to-human and human-to-digital handoffs across channels
• Experience with AI Voice, conversational IVR, browser or app-initiated calling, contact center platforms, telephony integration, and voice-to-agent escalation patterns
• Experience leading platform consolidation, capability reuse, shared services, or migration from fragmented product stacks
• Experience establishing AI evaluation, observability, human-in-the-loop, or model and content quality practices
• Experience operating high-volume or peak-season digital and contact-center experiences
• Passion for improving health care simplicity at scale, even if prior health care experience is limited

Benefits

• Comprehensive benefits package
• Incentive and recognition programs
• Equity stock purchase
• 401k contribution

Application Deadline

This will be posted for a minimum of 2 business days or until a sufficient candidate pool has been collected. Job posting may come down early due to volume of applicants.