VP Engagement Technology

Vice President Of 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.

Key Responsibilities:

• Engagement Strategy & Vision
• AI-Powered Engagement & Experience Innovation
• Cross-Functional Leadership & Stakeholder Alignment
• Vendor Management & Operational Excellence
• Team Leadership & Talent Development
• AI-Driven Industry Leadership

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 Mar Tech 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 Dev Ops 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, Guide Well 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.