Sr Director - Office of the CEO

GuideWell

4d

About The Position

The Chief of Staff serves as a strategic partner and trusted advisor to a
C-suite executive, providing executive-level strategic, operational, and
organizational leadership support to advance business growth, innovation,
performance, and operational excellence. This leader operates as an extension of
the executive, driving strategic clarity, operational discipline, organizational
alignment, and measurable business performance.

Requirements

• 10+ years of progressive leadership experience in strategic planning, operations, consulting, finance, or related fields within complex organizations
• Bachelor's degree in related discipline or additional related work experience
• Exceptional strategic thinking and enterprise-level business acumen
• Proven ability to convert complex information into strategy, and strategy into disciplined execution
• Strong executive presence with the ability to influence senior stakeholders and decision-makers
• Advanced project and program management expertise
• Demonstrated success operating in ambiguous, fast-paced environments
• Strong financial literacy and understanding of operational drivers
• Skilled at diagnosing issues early and mobilizing resources to resolve them
• Highly facilitative leadership style with strong interpersonal effectiveness
• Excellent written and verbal communication skills
• Strong ownership mindset and results orientation
• Ability to respectfully challenge assumptions and elevate decision quality
• Proficiency in Microsoft Office Suite

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 enterprise transformation, operational excellence, or corporate strategy functions
• Experience with change management and organizational effectiveness
• Exposure to enterprise-wide strategic planning and executive-level governance processes

Responsibilities

• Strategic Support & Advisory:
• Provide strategic counsel to the executive leader on key business initiatives, enterprise priorities, and performance objectives
• Translate enterprise objectives into integrated functional strategies and tactics and measurable execution plan
• Anticipate strategic risks and opportunities; provide actionable recommendations
• Represent the executive leader in key enterprise forums and decision-making settings
• Operational Oversight & Planning:
• Lead the annual strategic and business planning process for the functional area, ensuring alignment with enterprise objectives
• Oversee development, execution, and monitoring of short- and long-term strategic initiatives tied to financial and operational outcomes
• Drive accountability for goal achievement, performance metrics, and continuous improvement
• Ensure enterprise reporting alignment, including executive dashboards, monthly and quarterly operating reviews, and materials for executive leadership team, CEO, and board of directors
• Project & Initiative Leadership:
• Direct, monitor, and contribute to highly complex strategic projects involving multifaceted, cross-functional teams
• Serve as executive liaison to resolve issues and ensure successful implementation of company initiatives
• Lead or champion cross-functional teams supporting planning, development, and execution of key initiatives
• Identify and mitigate risks that could impact financial performance, operational stability, or organizational reputation
• Strong analysis, parsing large amounts of data in either excel or data analytics tools and present fact-based options to the Executive Leadership Team member
• Communication & Engagement:
• Communicate executive decisions clearly and monitor downstream execution
• Plan and execute leadership forums, town halls, and strategic summits
• Prepare and oversee executive presentations for internal and external audiences
• Foster a culture of innovation, inclusivity, accountability, and engagement aligned with enterprise values
• Talent, Change & Culture Leadership:
• Support talent development efforts in partnership with HR to build leadership pipeline and organizational capability
• Ensure effective communication of performance measures and business outcomes.
• Facilitate leadership meetings and develop executive-level content as needed

Benefits

• 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
• A comprehensive wellness program

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Number of Employees: 101-250 employees