Sr Director - Office of the CEO

GuideWell • Jacksonville, FL

1d

About The Position

The Sr Director of the Office of the CEO serves as a trusted operator and advisor to a C-suite executive, providing organizational leadership support to advance business growth, innovation, performance, and operational excellence. The role drives key initiatives and projects, tracks requests from the CEO and SVP Chief of Staff through completion, and works across the Executive Leadership Team (ELT) and broader organization. It operates as an extension of the executive to promote clarity, operational discipline, organizational alignment, and measurable business performance.

The position translates enterprise priorities into actionable work, maintains accountability for requests and performance, and manages CEO-priority initiatives. It serves as a liaison across executive and cross-functional teams, helps resolve issues and remove barriers, and identifies risks to business performance and stability. The Sr Director also supports executive communications and operating cadence, including leadership forums, town halls, strategic summits, ELT meetings, operating reviews, and board preparation.

The role requires extensive experience in a complex organization, strong project and program management expertise, business and financial acumen, executive presence, and the ability to influence senior stakeholders without direct authority. The position is sedentary, with occasional travel to multiple locations for meetings, events, or conferences.

Requirements

• 10+ years of progressive experience in operations, program management, strategic planning, consulting, finance, or related fields within complex organizations.
• Bachelor's degree in a related discipline or additional related work experience.
• Ability to turn priorities and direction into disciplined, on-time execution.
• Exceptional organization, attention to detail, and tenacious follow-through.
• Ability to manage many competing priorities and fast-changing requests simultaneously while maintaining attention to detail.
• Sound business judgment and enterprise-level business acumen, with the ability to advise senior leadership credibly.
• Strong executive presence and ability to influence and drive accountability among senior stakeholders and decision-makers without direct authority.
• Advanced project and program management expertise.
• Demonstrated success operating in ambiguous, fast-paced environments.
• Strong financial literacy and understanding of operational drivers.
• Ability to diagnose issues early and mobilize resources to resolve them.
• Highly facilitative leadership style and strong interpersonal effectiveness.
• Excellent written and verbal communication skills.
• Proficiency in Microsoft Office Suite.
• Exceptional discretion and ability to handle confidential information.
• Strong ownership mindset and results orientation.
• Ability to respectfully challenge assumptions and elevate decision quality.

Nice To Haves

• Master's degree.
• Knowledge of the health care industry.
• Experience in a Fortune 500 or similarly complex, highly matrixed enterprise.
• Prior experience in a chief of staff, office of the CEO, program management office, enterprise transformation, or operational excellence role.
• Experience with change management and organizational effectiveness.
• Exposure to executive-level governance processes and enterprise planning cycles.

Responsibilities

• Translate executive direction and enterprise priorities into action items with owners, deadlines, and next steps.
• Represent the Office of the CEO in enterprise forums and with ELT members as needed.
• Own intake, tracking, and closure of CEO and SVP Chief of Staff requests and action items, maintaining owners, due dates, and status.
• Drive accountability for goal achievement, performance metrics, and continuous improvement.
• Prioritize competing requests, escalate blockers and at-risk items, and manage sequencing in partnership with stakeholders.
• Capture decisions and commitments from CEO and ELT meetings, communicate them, and monitor downstream execution.
• Manage plans, milestones, dependencies, and status for CEO-priority initiatives and projects, taking hands-on action to advance progress as needed.
• Serve as executive liaison to ELT members and cross-functional teams to resolve issues, remove barriers, and support implementation of company initiatives.
• Support and convene cross-functional teams for planning, development, and execution of key initiatives.
• Identify and mitigate risks to financial performance, operational stability, or organizational reputation.
• Analyze data and develop concise, fact-based summaries and options for the CEO and ELT.
• Plan and execute leadership forums, town halls, and strategic summits.
• Prepare and oversee executive presentations for internal and external audiences.
• Support the CEO's operating cadence, including ELT meetings, monthly and quarterly operating reviews, and board preparation, by coordinating agendas, pre-reads, materials, and follow-up.
• Facilitate leadership meetings and develop executive-level content as needed.
• Foster a culture of innovation, accountability, inclusivity, and engagement aligned with enterprise values.
• Support leadership and talent efforts in partnership with HR as needed.

Benefits

• Medical, dental, vision, life, and global travel health insurance.
• Life insurance and short- and long-term disability programs.
• Leave programs to support personal circumstances.
• Retirement Savings Plan with employer match.
• Paid time off, volunteer time off, 10 holidays, and 2 well-being days.
• Additional voluntary benefits.
• Comprehensive wellness program.
• Competitive pay and opportunities for incentive or commission compensation.
• Annual reviews with pay-for-performance considerations for base pay increases.

What This Job Offers

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