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Job Description
The Director Executive Communications is a senior communications leader within GuideWell's Enterprise Communications function, responsible for serving as the strategic communications advisor, narrative architect, and a writer for GuideWell's President & CEO - and for ensuring the CEO and Executive Leadership Team's (ELT) voices, positioning, and presence are consistently expressed at the highest level across every arena that matters.
This is a strategic leadership role for someone who thinks at the level of the CEO, moves as fast as the organization demands, and brings to every interaction the rare combination of strategic instinct, editorial excellence, and proactive creative intelligence that makes a principal more effective - not just better prepared. The Director operates several moves ahead of what is being asked, converting signals from strategy sessions, leadership forums, and executive conversations into fully formed communications strategies before they are ever requested.
The Director reports directly to the VP of Communications and works in close daily partnership with the Sr. Director, Strategic Communications & Reputation to ensure the CEO's voice is always grounded in and advancing the enterprise narrative. The role also partners closely with the Sr. Director, Enterprise Communications (responsible for Media & Issues) on CEO media strategy and preparation, and with the SVP Chief of Staff on CEO schedule, priorities, and stakeholder relationships. This role also works hand in hand with the Executive Communications Consultant, who serves as the primary writer for the CEO, and the Thought Leadership lead, who owns thought leadership strategy and execution.
Key Responsibilities:
• Domain Ownership & Leadership: Serve as GuideWell's senior owner of CEO & Executive Communications - developing and maintaining a proactive, annually refreshed communications strategy that defines CEO/ELT external positioning, the audiences we should be reaching, the platforms right for their voices, and the narrative arc that connects individual communications moments into a coherent, building story.
• Content / Program Development & Execution: Own the development and quality of all CEO communications - speechwriting, thought leadership content, board and ELT presentations, media preparation materials, LinkedIn content, op-eds, and enterprise leadership communications - ensuring every piece reflects the CEO's authentic voice and GuideWell's highest editorial standard.
CEO Communications Strategy & Positioning
• Develop and maintain the CEO's thought leadership positioning - his authentic point of view on health transformation, affordability, AI-enabled care, and the not-for-profit model - ensuring it is distinctive, credible, and consistently expressed across every external platform.
• Identify opportunities to position the CEO in the national conversations that matter most to GuideWell's mission and strategy - health care affordability, integrated care delivery, the role of not-for-profit health systems, AI and the future of health.
• Monitor the national health care, policy, and business landscape continuously - tracking what peer CEOs are saying, where the industry conversation is moving, and where the CEO has an opportunity to lead rather than follow.
Speechwriting & Written Communications
• In partnership with the Executive Communications Consultant, serve as speechwriter to the CEO - developing remarks, keynote addresses, panel talking points, congressional testimony support, and enterprise-wide leadership communications that are unmistakably his voice: clear, direct, mission-driven, and narratively coherent.
• Write at the CEO level across every format - from a 45-minute keynote to a two-paragraph LinkedIn post to a board presentation.
• Develop and maintain a CEO voice guide - the documented standard for how he sounds, what he emphasizes, what he avoids, and the narrative principles that govern every piece of content that goes out under his name.
Board & ELT Communications
• Lead the development of CEO communications for the Board of Directors - board presentations, CEO updates, and the narrative framing of major organizational decisions.
• Support Executive Leadership Team communications that carry the CEO's voice - ensuring consistency, narrative alignment, and editorial quality.
• Develop communications for major enterprise moments - annual strategy presentations, transformation updates, organizational changes - ensuring the CEO's framing is clear, consistent, and grounded in the enterprise narrative.
Media Preparation & Thought Leadership Execution
• Partner with the Sr. Director, Enterprise Communications (Media & Issues) to prepare the CEO for all national media engagements - developing media briefs, message guides, Q&A preparation, and post-interview follow-through.
• Oversee the development, preparation for, and placement of executive thought leadership content - op-eds, bylined articles, published perspectives, speaking engagement prep, and industry commentary - in partnership with the Sr Communications Lead responsible for Executive Thought Leadership.
• Cross-Functional Integration: Work in close daily partnership with the Sr. Director, Strategic Communications & Reputation to ensure the CEO/ELT's voices are always grounded in and advancing the enterprise narrative. Partner with the Sr. Director, Enterprise Communications (Media & Issues) on CEO media strategy and preparation, and coordinate with the SVP Chief of Staff on CEO schedule, priorities, and stakeholder relationships.
• Stakeholder & Leader Support: Travel domestically with the CEO to major speaking engagements, industry conferences, policy forums, and stakeholder events - providing real-time communications counsel, on-site preparation support, and post-event follow-through. Serve as the on-the-ground communications presence at CEO events, ensuring the CEO is fully prepared on messaging and positioned to make the most of every interaction.
• Measurement & Continuous Improvement: Define and track success metrics for Executive Communications - measuring the CEO/ELT's external visibility, narrative consistency, audience reach, and contribution to GuideWell's national reputation. Maintain a rolling CEO communications opportunity log and brief the VP Comms regularly on what is in development, what is ready to activate, and where the program needs investment or adjustment.
• Proactive Intelligence & Ideation: Operate as the CEO's most attentive communications listener - present in strategy sessions and leadership forums with the explicit purpose of identifying the communications opportunities embedded in what the CEO is thinking, and bringing fully formed strategies back before they are requested. Convert signals into strategies: a story shared about a member encounter becomes a thought leadership piece; a reaction to a competitor's move becomes a positioning statement.
Key Requirements:
• 12+ years' progressive related experience to include executive communications, speechwriting, strategic communications, or a closely adjacent discipline - with demonstrated experience serving as a primary communications advisor and writer for a C-suite principal.
• Bachelor's degree in Communications, Journalism, English, Public Relations, or related field or additional related work experience
• Proven track record as a CEO-level speechwriter and strategic communications advisor - able to write in an executive's authentic voice across every format, from keynote addresses to board presentations to op-eds.
• Experience developing and executing proactive CEO thought leadership strategies - not just responding to communications requests but anticipating needs and identifying opportunities before they are articulated.
• Understanding of the health care industry - sufficient to develop credible CEO positioning on health transformation, affordability, AI, and integrated care delivery without requiring constant subject matter briefing.
• Demonstrated experience operating with high confidentiality and discretion in a C-suite communications environment.
• Exceptional strategic instinct - hears a conversation or offhand observation and immediately sees the communications opportunity and the strategy to pursue it.
Preferred:
• Experience supporting a CEO or equivalent principal in a complex, mission-driven, or regulated organization - health care, health insurance, not-for-profit, or public sector.
• Background in journalism, political communications, or a discipline demanding both exceptional writing speed and strategic judgment under pressure.
• Experience developing CEO thought leadership in national health care, policy, or business media.
• Familiarity with the Blue Cross Blue Shield system, managed care, or integrated health services landscape.
• Experience traveling with and providing real-time communications support to a senior executive principal
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.
Physical/Environmental Activities
Must be able to travel to multiple locations for work (i.e. travel to attend meetings, events, conferences). Frequently
What We Offer:
As a Florida Blue employee, you will be at the heart of GuideWell's vision - to lead the nation in transforming health through compassionate, connected, and technology-enabled care that delivers personalized value and empowered living.
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.
Annualized Salary Range: $126,000 - $204,800
Typical Annualized Hiring Range: $126,000 - $157,500
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.