Strategic Planning & Executive Support Analyst

The Strategic Planning & Executive Support Analyst provides senior-level strategic, operational, and administrative support to REMD executive leadership, including the Executive Director (ED), Deputy Executive Director (DED), and Assistant Administrator/Chief Administrative Officer (CAO). This position plays a critical role in advancing high-priority TSA initiatives by delivering executive communications, performance tracking, risk management, stakeholder coordination, and process improvement support. The role extends beyond traditional administrative functions and requires proactive ownership of complex assignments, expert advisement, and cross-functional collaboration to drive organizational objectives.

Responsibilities

• Provide executive-level support in developing, reviewing, and refining TSA processes, procedures, documentation, artifacts, and briefing materials.
• Assume ownership of assigned actions; coordinate draft and financial concurrence across REMD and SAS departments.
• Develop talking points, speeches, presentations, testimony, fact sheets, Welcome Packets, intranet updates, and internal/external communications regarding planning and construction impacts.
• Plan and coordinate Town Halls and quarterly REMD All Hands meetings (three virtual/hybrid and one in-person annually), including agenda development, presentation creation, and logistics management.
• Develop and maintain the REMD Risk Register, including designing and conducting expert elicitation sessions to inform risk analyses.
• Draft functional performance metrics and objectives for Real Estate programs and track progress against strategic goals.
• Prepare weekly leadership status briefs, dashboards, milestone tracking reports, and quarterly accomplishment summaries (“placemat”).
• Collect, analyze, and synthesize qualitative and quantitative data to support leadership decision-making across CSO, PMD, OSHE, and REMD divisions.
• Manage the REMD Tasking Mailbox (approximately eight taskings per day); assign, coordinate, and track responses through completion while maintaining organized electronic records.
• Aid federal staff in responding to oversight inquiries (OMB, DHS, Congress) and stakeholder inquiries (TSA organizations, airlines, airports, lessors, GSA).
• Facilitate working sessions and scoping meetings; define issues, develop options, recommend paths forward, and manage execution through final delivery.
• Develop and document standard operating procedures (SOPs) for SAS front office functions.
• Identify process gaps, inefficiencies, or risks and recommend improvements to enhance operational effectiveness and compliance.
• Serve as liaison between leadership, internal departments, and external stakeholders.
• Perform other job-related duties as assigned.

Qualifications

• Bachelor’s degree in Business Administration, Public Administration, Real Estate, Communications, or related field (Master’s preferred).
• Minimum of 7–10 years of progressive experience supporting executive leadership in a federal, regulatory, or complex organizational environment.
• Demonstrated experience in strategic communications, performance management, risk analysis, and stakeholder engagement.
• Strong analytical, organizational, and facilitation skills with the ability to manage multiple high-priority initiatives simultaneously.
• Experience preparing executive briefings, congressional or oversight responses, and high-visibility communications preferred.

This position is restricted to U.S. citizens or legal permanent residents. Documentation of U.S. citizenship or legal permanent residency is required to qualify.

Benefits

Compensation & Benefits: Estimated Starting Salary Range for Strategic Planning & Executive Support Analyst: TBD. Pay commensurate with experience. Full-time benefits include Medical, Dental, Vision, 401K, and other possible benefits as provided. Benefits are subject to change with or without notice.

About the Role

Cherokee Federal is a military friendly employer. Veterans and active military transitioning to civilian status are encouraged to apply.

Keywords

• Strategic Planning
• Executive Support
• Risk Management
• Performance Metrics
• Stakeholder Engagement

Legal Disclaimer

All qualified applicants will receive consideration for employment without regard to protected veteran status, disability or any other status protected under applicable federal, state or local law. Many of our job openings require access to government buildings or military installations. Please Note: This position is pending a contract award. If you are interested in a future with Cherokee Federal, APPLY TODAY! Although this is not an approved position, we are accepting applications for this future and anticipated need.