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 against strategic priorities
* Own roadmap execution: project prioritization, resource allocation, delivery accountability
Team Leadership & Talent Development
* 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
AI-Driven Industry Leadership
* 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

Key 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)

Preferred:
* 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

General Physical Demands
Sedentary work: Exerting up to 10 pounds of force occasionally to move objects. Jobs are sedentary if traversing activities are required only occasionally

What We Offer:
As a Florida Blue employee, you will thrive in our Be Well, Work Well, GuideWell culture where being well as an individual, and working well as a team, are both important in serving our members and communities.

To support your wellbeing, comprehensive benefits are offered. As an employee, you will have access to:

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; and

A comprehensive wellness program

Employee benefits are designed to align with federal and state employment laws. Benefits may vary based on the state in which work is performed. Benefits for intern, part-time and seasonal employees may differ.

To support your financial wellbeing, we offer competitive pay as well as opportunities for incentive or commission compensation. We also conduct regular annual reviews with pay for performance considerations for base pay increases.

Final pay will be determined with consideration of market competitiveness, internal equity, and the job-related knowledge, skills, training, and experience you bring.

We are an Equal Employment Opportunity employer committed to cultivating a work experience where everyone feels like they belong and can perform at their best in pursuit of our mission. All qualified applicants will receive consideration for employment.