Executive Assistant

Executive Assistant

Location: Bethesda, MD
Work Type: Full Time (Onsite)
Clearance: Top Secret SCI CI Poly


Position Summary: The Executive Assistant (Operations & Executive Support) provides high-level operational, administrative, and executive support to designated leaders by managing the operating rhythm of the office, coordinating cross-stakeholder priorities, and independently resolving day-to-day operational issues. The role requires sound judgment, discretion, and independent decision-making to triage competing demands, protect leader time, and drive timely execution of business-critical activities.
This position performs office/non-manual work supporting management and/or general business operations and is expected to exercise discretion and independent judgment on matters of significance.

Essential Duties & Responsibilities (Primary)
1) Executive enablement & operating rhythm

• Owns leader(s) calendars as a strategic resource: prioritizes requests, resolves conflicts, and recommends tradeoffs aligned to business priorities.
• Designs and manages meeting cadences (e.g., leadership syncs, stakeholder touchpoints), including agendas, pre-reads, attendee alignment, and action/decision capture.
• Drafts and refines executive communications (emails, announcements, briefings) requiring judgment, confidentiality, and appropriate tone.

2) Operational coordination & issue resolution

• Serves as an operational hub across multiple stakeholders/offices to ensure commitments are met; identifies blockers early and drives closure through follow-up, escalation, and recommended paths forward.
• Independently handles sensitive/confidential matters (e.g., personnel-related scheduling, mission/client-sensitive topics) using discretion and appropriate escalation.
• Maintains and improves office "standard work" (playbooks, checklists, templates) and recommends process changes to improve speed, quality, and consistency.

3) Project, task, and workflow management

• Leads and coordinates discrete projects/initiatives on behalf of leadership (e.g., event planning, onboarding/offboarding coordination, quarterly planning logistics, cross-team deliverable tracking), including timelines, dependencies, and status reporting.
• Translates ambiguous requests into clear scope, owners, milestones, and deliverables; proactively identifies risks and mitigation options.

4) Travel, logistics, and resource optimization

• Plans and coordinates travel and logistics end-to-end, including proactive optioning (cost/time/risk tradeoffs), itinerary optimization, and issue resolution during travel disruptions.
• Coordinates space/room logistics and meeting execution to minimize friction and maximize leader effectiveness.
• Coordinates vendor and resource needs within established guidelines; obtains options/quotes as needed, recommends selections, and executes within delegated approval parameters.

5) Stakeholder management & business partnering

• Builds effective working relationships with internal partners (e.g., operations, finance, procurement, HR, security, IT) to execute time-sensitive requests and resolve issues quickly.
• Anticipates leadership needs through pattern recognition and proactive recommendations (e.g., capacity constraints, sequencing, communications timing).

Decision-Making & Delegated Authorities
The role is expected to exercise independent judgment within established guidelines. Examples may include:

• Reprioritizing calendar requests based on leader priorities and business impact.
• Selecting among travel/logistics options within approved policy and budget guardrails.
• Determining when to escalate issues, proposing recommended solutions, and coordinating execution once direction is confirmed.

Minimum Qualifications

• Demonstrated experience supporting senior leaders in a complex, fast-paced environment requiring discretion and independent judgment.
• Strong project/workflow management skills (planning, dependency management, follow-through, risk identification).
• Strong written and verbal communication skills, including drafting executive-ready materials.
• High proficiency with standard productivity and collaboration tools (calendar, email, document and meeting platforms).
• Ability to handle confidential information with professionalism and care.

Preferred Qualifications

• Experience coordinating across multiple teams/offices and navigating competing priorities.
• Experience improving administrative/operational processes (templates, playbooks, workflows).
• Experience supporting work in regulated or government/federal contract-adjacent environments (as applicable).

Senior Executive Assistant

• Provides day-to-day guidance to junior administrative staff; reviews work for quality/consistency, shares best practices, and helps standardize team processes.
• Leads small administrative/operations improvements impacting multiple leaders/offices.

Clearance: Applicants selected will be subject to a security investigation and may need to meet eligibility requirements for access to classified information.
Compensation and Benefits
Salary Range: $110,000-$165,000 (Compensation is determined by various factors, including but not limited to location, work experience, skills, education, certifications, seniority, and business needs. This range may be modified in the future.)
Benefits: Gridiron offers a comprehensive benefits package including medical, dental, vision insurance, HSA, FSA, 401(k), disability & ADD insurance, life and pet insurance to eligible employees. Full-time and part-time employees working at least 30 hours per week on a regular basis are eligible to participate in Gridiron's benefits programs.
Gridiron IT Solutions is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, pregnancy, sexual orientation, gender identity, national origin, age, protected veteran status or disability status.
Gridiron IT is a Women Owned Small Business (WOSB) headquartered in the Washington, D.C. area that supports our clients' missions throughout the United States. Gridiron IT specializes in providing comprehensive IT services tailored to meet the needs of federal agencies. Our capabilities include IT Infrastructure & Cloud Services, Cyber Security, Software Integration & Development, Data Solution & AI, and Enterprise Applications. These capabilities are backed by Gridiron IT's experienced workforce and our commitment to ensuring we meet and exceed our clients' expectations.