Project Specialist - Executive Office

Overview

The Project Specialist - Executive Office serves as a strategic partner to the CEO and Chief of Staff. Reporting directly to and working closely with the Chief of Staff, this role helps coordinate, align, and accelerate progress across five key functional areas: CEO Office Team, Board of Managers, Enterprise Project Management, Process Improvement Initiatives, and Healthcare System Strategy.

This position demands a self-starter with strong project management expertise who can independently develop comprehensive presentations, workshop materials, and strategic documentation for high-stakes audiences including City Council and executive leadership. Working in close partnership with the Chief of Staff, the successful candidate will create and storyboard presentations and develop formal project charters while applying Lean Management Principles to drive organizational efficiency.

This position will synthesize complex information across finance, operations, and strategy within the healthcare system, requiring both analytical rigor and the ability to translate technical concepts into compelling executive communications. Regular reporting and strategic planning sessions with the Chief of Staff will ensure alignment with organizational priorities and executive directives.

This role offers significant exposure to C-suite decision making and Board of Managers' operations, making it ideal for a detail-oriented professional seeking to advance their strategic project management career.

The position requires someone who can excel in a fast-paced environment with minimal supervision while maintaining the high standards expected of CEO Office deliverables. The role involves serving as a key liaison between the Chief of Staff and various departments, ensuring seamless communication and project coordination. The work will directly impact organizational strategy and executive decision-making, requiring discretion, professionalism, and the ability to manage competing priorities across multiple high-visibility initiatives simultaneously under the guidance and strategic direction of the Chief of Staff.

Essential Functions:

CEO Office Team Operations
• Collaborate with the Chief of Staff to develop and execute strategic initiatives for the CEO Office Team, ensuring alignment with organizational priorities
• Maintain confidential executive communications and ensure seamless information flow between the Chief of Staff, CEO, and key stakeholders
• Manage executive-level correspondence and documentation with appropriate confidentiality and discretion Board of Managers Support
• Prepare comprehensive Board materials including agenda packets, meeting minutes, strategic presentations, and executive briefing documents
• Coordinate with the Chief of Staff to ensure Board materials align with executive messaging and strategic priorities Track and manage Board action items and directives, ensuring timely completion through systematic follow-up processes and progress reporting to the Chief of Staff
• Develop Board reporting templates and standardize documentation processes for consistency and quality Enterprise Project Management
• Create formal project charters, statements of work (SOWs), and project documentation with Chief of Staff approval and strategic guidance
• Lead cross-departmental project initiatives from conception through implementation, serving as the CEO Office representative
• Develop and maintain project timelines, milestones, and deliverable tracking systems with regular status reporting to the Chief of Staff
• Facilitate project meetings and ensure accountability across all stakeholders, escalating issues and risks to the Chief of Staff as appropriate
• Manage project budgets, resource allocation, and vendor relationships within established parameters Executive Presentation Development
• Design and create PowerPoint presentations for CEO, Internal, and External Stakeholder audiences following Chief of Staff review and approval processes
• Write accompanying presentation scripts and develop detailed storyboards that align with executive messaging strategies
• Synthesize complex financial, operational,…