Strategic Planning & Executive Support Analyst

Cherokee Federal•Springfield, VA

About The Position

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.

Requirements

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.
Must pass pre-employment qualifications of Cherokee Federal

Nice To Haves

Experience preparing executive briefings, congressional or oversight responses, and high-visibility communications preferred.

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.
Assist 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.
Performs other job-related duties as assigned