Executive Assistant
System One Holdings, LLC
Executive Assistant
Location: Vienna, VA (Full-time on site) Pay Rate: Open to Both C2C and W2 options Position Type: Contract
We are seeking a highly experienced, polished, and proactive Executive Assistant to provide dedicated support to the VP Planning & Optimization. This six-month contractor role requires an individual who can operate with a high degree of professionalism, discretion, urgency, and independent judgment in a fast-paced executive environment. The ideal candidate will have extensive experience supporting senior executives, preferably in a large, complex, highly matrixed organization. This individual must be highly organized, detail-oriented, resourceful, and comfortable managing competing priorities while maintaining strong follow-through and confidentiality. This role is best suited for someone who understands executive-level support is not only administrative, but also operationally critical.
The Executive Assistant will help ensure the VP Planning & Optimization is prepared, organized, and able to focus on strategic priorities by managing calendars, communications, meeting logistics, travel, expenses, materials, and day-to-day coordination across internal and external stakeholders.
Key Responsibilities
- Executive Calendar and Time Management
- Manage a complex and dynamic executive calendar, ensuring the VP Planning & Optimization's time is prioritized effectively and aligned to business needs
- Anticipate scheduling conflicts, resolve issues proactively, and ensure the executive is prepared for upcoming meetings, events, and deliverables
- Coordinate meetings across senior leaders, internal teams, external partners, vendors, and other stakeholders
- Apply sound judgment when prioritizing requests, escalating urgent matters, and protecting time for high-priority work
- Meeting Coordination and Preparation
- Plan and coordinate executive meetings, leadership discussions, vendor meetings, and cross-functional working sessions
- Prepare agendas, organize materials, capture notes or action items when needed, and ensure follow-up items are tracked to completion
- Partner with internal teams to gather and organize materials for meetings, presentations, briefings, and executive updates
- Ensure the VP Planning & Optimization has the right information, context, and materials in advance of key meetings
- Communication and Stakeholder Support
- Serve as a professional and trusted point of contact for internal and external stakeholders
- Draft, review, proofread, and format correspondence, meeting materials, and other executive communications as needed
- Handle sensitive information with the highest level of confidentiality and discretion
- Represent Procurement & Vendor Management with professionalism, responsiveness, and sound judgment
- Travel, Expense, and Administrative Support
- Coordinate domestic travel arrangements, including flights, lodging, transportation, itineraries, and meeting logistics
- Prepare and submit expense reports accurately and in a timely manner
- Support administrative processes, including purchase requests, invoices, vendor coordination, onboarding logistics, and other operational needs as required
- Maintain organized records, files, contact lists, distribution lists, and relevant documentation
- Operational and Project Coordination
- Support the VP Planning & Optimization by tracking priorities, deadlines, action items, and follow-ups across key workstreams
- Assist with coordination of procurement-related meetings, leadership routines, vendor engagements, and internal business reviews
- Help organize information and maintain visibility into commitments, decisions, and pending items
- Identify opportunities to improve administrative processes, increase efficiency, and create smoother day-to-day operations for the executive
Required Qualifications
- Minimum of 7 to 10 years of experience providing executive-level administrative support, preferably to a senior executive, C-suite leader, or equivalent
- Demonstrated experience managing complex calendars, competing priorities, confidential information, and senior-level stakeholder interactions
- Strong proficiency with Microsoft Office applications, including Outlook, Teams, Word, Excel, and PowerPoint
- Excellent written and verbal communication skills, with strong attention to detail and professional polish
- Ability to work independently, anticipate needs, solve problems, and make sound decisions with limited direction
- Strong organizational skills with the ability to manage multiple priorities, deadlines, and stakeholders simultaneously
- High degree of discretion, integrity, and professionalism when handling sensitive or confidential matters
- Experience supporting executives in a large corporate, financial services, procurement, supply chain, vendor management, or similarly complex environment preferred
Preferred Qualifications
- Prior experience supporting a VP or other senior operations-focused executive
- Experience working with procurement, vendor management, sourcing, contracts, or third-party risk teams
- Familiarity with tools such as Concur, ServiceNow, SharePoint, SAP, Oracle, or similar enterprise systems
- Experience coordinating executive meetings with external vendors, consultants, legal partners, or senior business leaders
- Ability to quickly learn organizational norms, stakeholder relationships, and executive preferences
Key Competencies
- Strong executive presence and professionalism
- High attention to detail
- Exceptional organization and follow-through
- Ability to anticipate needs before being asked
- Sound judgment and discretion
- Clear, concise communication
- Comfort operating in ambiguity
- Responsiveness and reliability
- Ability to build trust quickly with executives and stakeholders
- A service-oriented mindset with the confidence to manage up appropriately
Success in This Role Looks Like
- The VP's calendar, meetings, travel, and day-to-day priorities are managed smoothly and proactively
- The executive is consistently prepared for meetings and key deliverables
- Stakeholders experience timely, professional, and clear coordination
- Administrative processes are handled accurately and with minimal follow-up required
- Confidential information is managed appropriately and discreetly
- The contractor quickly becomes a trusted, reliable extension of the VP's office during the six-month assignment
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