VP Engagement Technology

The Vice President of Engagement Technology owns the strategy, product roadmap, and business outcomes for the member, broker, and provider engagement layer – digital, mobile, CRM/Mar Tech, contact center orchestration, and provider-facing experience tools – across Medicare Advantage, Medicaid, Commercial, and ACA Exchange.

This leader will advance AI capabilities into every corner of the engagement experience – conversational AI, agentic workflows, hyper-personalization, and predictive, proactive outreach – translating acquisition, retention, and activation goals into product requirements and AI-powered features that make Guide Well’s digital experience an industry benchmark. Serves as the engagement technology advisor to the CIO and C‑suite on digital engagement and AI investment.

• Define and operationalize a 3-5 year engagement technology strategy with AI as a core differentiator, aligning to member acquisition cost targets, retention lift, and health activation KPIs across all lines of business.
• Serve as engagement technology advisor to the CIO and C‑suite, providing quarterly business case analysis, ROI projections, and competitive benchmarking for digital engagement, AI-powered omnichannel, and Mar Tech investments.
• Lead rationalization of the engagement technology portfolio – CRM, marketing automation, member/provider apps, contact center – against integration feasibility, TCO, and strategic fit; build a 12‑24 month modernization roadmap that centers AI-native capability.
• Establish governance for engagement technology and AI feature investment decisions, including steering committees, business case standards, and quarterly executive reviews.
• Own and continuously advance an AI-powered engagement roadmap – generative and conversational AI, agentic self‑service workflows, hyper-personalized content and offers, and predictive/proactive outreach – positioning Guide Well as an industry benchmark for AI-driven digital health engagement.
• Own the orchestration layer and business logic for an omnichannel engagement experience – sequencing, personalization rules, and channel selection across digital, mobile, contact center, chatbots, and marketing touchpoints.
• Define requirements for and execute on AI-powered engagement features – conversational AI, next‑best‑action recommendations, predictive outreach, sentiment-aware routing – driving adoption and measurable performance against business KPIs.
• Rapidly evaluate and pilot emerging AI capabilities (agentic AI, generative content, voice AI) and translate them into shipped, differentiated member and provider experiences.
• Benchmark Guide Well’s AI-powered engagement experience against best-in-class consumer and health plan digital experiences; set and track a roadmap to close gaps and lead the market.
• Own the member and provider experience across the full lifecycle (acquisition, onboarding, ongoing engagement, claims resolution, renewal, retention), with accountability for self-service adoption, first-contact resolution, and CSAT/NPS.
• Own CRM and Mar Tech platform strategy and administration – marketing automation, campaign management, AI-driven audience activation – as the primary business owner.
• Partner with Marketing, Customer Experience, and Sales to align the AI-powered engagement roadmap with member acquisition, broker enablement, and sales productivity objectives; run periodic business reviews on campaign performance and tool effectiveness.
• Partner with Member Experience and Clinical Operations to ensure AI-powered engagement technology drives health activation, care coordination, and clinical outcomes; define requirements for wellness, care navigation, and health equity.
• Establish a compliance governance framework with Legal covering CMS Medicare Advantage marketing rules, Medicaid state requirements, ACA Exchange regulations, HIPAA, and WCAG 2.1 AA accessibility standards, including responsible‑AI guardrails for member-facing AI features.
• Partner with IT Operations and Security to ensure engagement and AI platforms meet enterprise security, privacy, and business continuity standards.
• Establish and oversee a Vendor Management Office for…