Sr Director - Office of the CEO

GuideWell • Jacksonville, FL

7h • $168,000 - $273,000

About The Position

The Sr Director, Office of the CEO (OCEO), 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 the broader organization. Operating as an extension of the executive, the Sr Director drives clarity, operational discipline, organizational alignment, and measurable business performance.

The role translates enterprise priorities into accountable action, manages executive requests and initiative execution, coordinates cross-functional teams, identifies and mitigates risks, and analyzes information for executive decision-making. It also supports the CEO's operating cadence and executive communications, including leadership forums, town halls, strategic summits, ELT meetings, operating reviews, and board preparation.

The position requires occasional travel to multiple locations for meetings, events, and conferences. The work is sedentary, with occasional exertion of up to 10 pounds to move objects.

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.
• Proven 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 without losing sight of details.
• Sound business judgment and enterprise-level business acumen, with the ability to serve as a credible advisor to senior leadership.
• 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.
• Skill in diagnosing issues early and mobilizing 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 direction and enterprise priorities into clear action items with owners, deadlines, and next steps.
• Represent the OCEO 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 in a single source of truth.
• Drive accountability for goal achievement, performance metrics, and continuous improvement.
• Prioritize and sequence competing requests in partnership, and escalate blockers and at-risk items early.
• Capture decisions and commitments from CEO and ELT meetings, communicate them clearly, and monitor downstream execution.
• Manage plans, milestones, dependencies, and status for CEO priority initiatives and projects, taking hands-on action as needed to drive progress.
• Serve as executive liaison to ELT members and cross-functional teams to resolve issues, remove barriers, and ensure successful implementation of company initiatives.
• Support and convene cross-functional teams for planning, development, and execution of key initiatives.
• Identify and mitigate risks that could affect financial performance, operational stability, or organizational reputation.
• Analyze data and prepare 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 through 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, and support leadership and talent efforts with HR as needed.

Benefits

• Medical, dental, vision, life, and global travel health 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.
• Comprehensive wellness program.
• Competitive pay and 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: Director