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/MarTech, 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 GuideWell's digital experience an industry benchmark. Serves as the engagement technology advisor to the CIO and C-suite on digital engagement and AI investment.

Key Responsibilities:
Engagement Strategy & Vision
•    Define and operationalize a 3–5 year engagement technology strategy — with AI as a core differentiator, not an add-on — with explicit alignment 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 MarTech 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 puts AI-native capability at the center
•    Establish governance for engagement technology and AI feature investment decisions, including steering committees, business case standards, and quarterly executive reviews
AI-Powered Engagement & Experience Innovation
•    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 — that positions GuideWell 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 GuideWell'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 MarTech platform strategy and administration — marketing automation, campaign management, AI-driven audience activation — as the primary business owner
Cross-Functional Leadership & Stakeholder Alignment
•    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
Vendor Management & Operational Excellence
•    Establish and oversee a Vendor Management Office for engagement technology — CRM, marketing automation, contact center/telephony, broker portal, member/provider apps, and AI/engagement tooling — including performance monitoring and contract governance
•    Drive SLAs, performance metrics, and continuous improvement processes across engagement and AI-powered platforms
•    Manage engagement technology budget and capital allocation, ensuring optimal ROI ag