VP Engagement Technology

Florida Blue • FL, FL

1d

About The Position

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.

Requirements

• Bachelor's degree in Computer Science, Information Technology, Business Administration, or related field (or equivalent professional experience)
• 15+ years of progressive technology or digital product leadership, including 7+ years at VP-level or equivalent leading engagement, digital AI, or MarTech organizations
• 10+ years hands-on experience with engagement-layer platforms: Digital engagement platforms, member/provider portals, mobile apps, CRM and marketing automation / customer data activation (Salesforce, Microsoft Dynamics, SFMC, Hightouch, or equivalent), conversational and generative AI-powered engagement features shipped in production, with demonstrated ownership from requirements through adoption and measurable outcomes
• Demonstrated track record of shipping industry-leading, AI-powered engagement experiences — generative AI, agentic workflows, hyper-personalization, predictive outreach — with measurable adoption and dollarized business impact
• Demonstrated success leading engagement technology transformations at scale: Managed engagement technology portfolios with $5M+ annual budgets. Delivered platforms or products affecting 500K+ members or patients. Delivered measurable, dollarized business outcomes (e.g., AI-driven call deflection, engagement lift, digital adoption improvement)
• Deep understanding of health plan operations, including Medicare Advantage, Medicaid, Commercial, and ACA Exchange business models, member lifecycle management, and regulatory requirements (CMS, state insurance departments, HIPAA)

Nice To Haves

• MBA or equivalent advanced business degree preferred
• Prior experience in health plan, health insurance, or healthcare technology environments
• Demonstrated expertise in Medicare Advantage engagement technology and member acquisition strategies
• Hands-on experience with broker and producer technology platforms
• Board-level presentation experience or experience supporting board-level technology and AI strategy discussions
• Experience with agile and DevOps transformation in enterprise environments

Responsibilities

• 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
• 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
• 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 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 against strategic priorities
• Own roadmap execution: project prioritization, resource allocation, delivery accountability
• Build and lead a high-performing engagement technology team of product managers, channel/experience architects, and MarTech platform engineers with strong AI fluency
• Establish clear accountability for platform performance, AI feature adoption, and business outcomes
• Foster a culture of rapid experimentation and end-to-end product ownership — discovery through launch and iteration — in close partnership with business, clinical, and consumer stakeholders
• Establish GuideWell's engagement experience as an industry-leading example of applied AI in health plan member and provider interaction
• Track and translate industry and competitor AI/digital engagement trends into GuideWell's roadmap ahead of the market
• Represent GuideWell's AI-powered engagement work in external, board, and industry-facing settings as evidence of enterprise AI value

Benefits

• Medical, dental, vision, life and global travel health insurance
• Income protection benefits: life insurance, short- and long-term disability programs
• Leave programs to support personal circumstances
• Retirement Savings Plan including employer match
• Paid time off, volunteer time off, 10 holidays and 2 well-being days
• Additional voluntary benefits available
• A comprehensive wellness program
• Competitive pay
• Opportunities for incentive or commission compensation
• Regular annual reviews with pay for performance considerations for base pay increases

What This Job Offers

• Job Type: Full-time
• Career Level: Executive