Senior Director, CEO Office — Strategic Programs Lead

GuideWell; Jacksonville (FL); On-site; USD 168,000 - 273,000; Full time

Benefits offered by this job

Medical Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

Retirement Match

PTO

Job summary

GuideWell is seeking a Sr Director, Office of the CEO, to serve as a trusted advisor to the CEO and SVP Chief of Staff. You will drive organizational leadership, track CEO requests to completion, and partner with the ELT to advance growth, performance, and operational excellence.

You will translate priorities into actionable plans, own risk management, and ensure clear communication across senior stakeholders. A focus on governance, planning cycles, and execution is essential in this role.

Qualifications

• 10+ years of progressive experience in operations, program management, strategic planning, consulting, finance, or related fields within complex organizations.
• Bachelor's degree in 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

Responsibilities

• Translate direction and 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/ SVP Chief of Staff requests with owners, due dates, and status
• Drive accountability for goal achievement, performance metrics, and continuous improvement
• Prioritize and sequence competing requests in partnership; elevate blockers and at-risk items
• Capture decisions and commitments from CEO/ELT and monitor downstream execution
• Manage plans, milestones, dependencies, and status; step in hands‑on when needed
• Serve as executive liaison to ELT and cross‑functional teams to resolve issues
• Support cross‑functional planning and execution of key initiatives
• Identify and mitigate risks impacting financial performance, operations, or reputation
• Analyze data and distill it into concise summaries for CEO/ELT
• Communicate executive decisions clearly and monitor downstream execution
• Plan leadership forums, town halls, and strategic summits
• Prepare executive presentations for internal and external audiences
• Support CEO operating cadence via agendas, pre‑reads, materials, and follow‑ups
• Facilitate leadership meetings and develop executive‑level content
• Foster a culture of innovation, accountability, inclusivity, and engagement

Skills

Executive presence

Strategic planning

Project management

Cross-functional leadership

Financial literacy

Communication

Problem solving

Education

Bachelor's degree in related discipline

Master's degree (preferred)

Tools

Microsoft Office Suite

Job description

GuideWell is seeking a Sr Director, Office of the CEO, to serve as a trusted advisor to the CEO and SVP Chief of Staff. You will drive organizational leadership, track CEO requests to completion, and partner with the ELT to advance growth, performance, and operational excellence.

You will translate priorities into actionable plans, own risk management, and ensure clear communication across senior stakeholders. A focus on governance, planning cycles, and execution is essential in this role.