Executive Assistant
System One Holdings, LLC
Executive AssistantLocation: Vienna, VA (Full-time on site) Pay Rate: Open to Both C2C and W2 options Position Type: ContractWe 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 ResponsibilitiesExecutive Calendar and Time ManagementManage a complex and dynamic executive calendar, ensuring the VP Planning & Optimization's time is prioritized effectively and aligned to business needsAnticipate scheduling conflicts, resolve issues proactively, and ensure the executive is prepared for upcoming meetings, events, and deliverablesCoordinate meetings across senior leaders, internal teams, external partners, vendors, and other stakeholdersApply sound judgment when prioritizing requests, escalating urgent matters, and protecting time for high-priority workMeeting Coordination and PreparationPlan and coordinate executive meetings, leadership discussions, vendor meetings, and cross-functional working sessionsPrepare agendas, organize materials, capture notes or action items when needed, and ensure follow-up items are tracked to completionPartner with internal teams to gather and organize materials for meetings, presentations, briefings, and executive updatesEnsure the VP Planning & Optimization has the right information, context, and materials in advance of key meetingsCommunication and Stakeholder SupportServe as a professional and trusted point of contact for internal and external stakeholdersDraft, review, proofread, and format correspondence, meeting materials, and other executive communications as neededHandle sensitive information with the highest level of confidentiality and discretionRepresent Procurement & Vendor Management with professionalism, responsiveness, and sound judgmentTravel, Expense, and Administrative SupportCoordinate domestic travel arrangements, including flights, lodging, transportation, itineraries, and meeting logisticsPrepare and submit expense reports accurately and in a timely mannerSupport administrative processes, including purchase requests, invoices, vendor coordination, onboarding logistics, and other operational needs as requiredMaintain organized records, files, contact lists, distribution lists, and relevant documentationOperational and Project CoordinationSupport the VP Planning & Optimization by tracking priorities, deadlines, action items, and follow-ups across key workstreamsAssist with coordination of procurement-related meetings, leadership routines, vendor engagements, and internal business reviewsHelp organize information and maintain visibility into commitments, decisions, and pending itemsIdentify opportunities to improve administrative processes, increase efficiency, and create smoother day-to-day operations for the executiveRequired QualificationsMinimum of 7 to 10 years of experience providing executive-level administrative support, preferably to a senior executive, C-suite leader, or equivalentDemonstrated experience managing complex calendars, competing priorities, confidential information, and senior-level stakeholder interactionsStrong proficiency with Microsoft Office applications, including Outlook, Teams, Word, Excel, and PowerPointExcellent written and verbal communication skills, with strong attention to detail and professional polishAbility to work independently, anticipate needs, solve problems, and make sound decisions with limited directionStrong organizational skills with the ability to manage multiple priorities, deadlines, and stakeholders simultaneouslyHigh degree of discretion, integrity, and professionalism when handling sensitive or confidential mattersExperience supporting executives in a large corporate, financial services, procurement, supply chain, vendor management, or similarly complex environment preferredPreferred QualificationsPrior experience supporting a VP or other senior operations-focused executiveExperience working with procurement, vendor management, sourcing, contracts, or third-party risk teamsFamiliarity with tools such as Concur, ServiceNow, SharePoint, SAP, Oracle, or similar enterprise systemsExperience coordinating executive meetings with external vendors, consultants, legal partners, or senior business leadersAbility to quickly learn organizational norms, stakeholder relationships, and executive preferencesKey CompetenciesStrong executive presence and professionalismHigh attention to detailExceptional organization and follow-throughAbility to anticipate needs before being askedSound judgment and discretionClear, concise communicationComfort operating in ambiguityResponsiveness and reliabilityAbility to build trust quickly with executives and stakeholdersA service-oriented mindset with the confidence to manage up appropriatelySuccess in This Role Looks LikeThe VP's calendar, meetings, travel, and day-to-day priorities are managed smoothly and proactivelyThe executive is consistently prepared for meetings and key deliverablesStakeholders experience timely, professional, and clear coordinationAdministrative processes are handled accurately and with minimal follow-up requiredConfidential information is managed appropriately and discreetlyThe contractor quickly becomes a trusted, reliable extension of the VP's office during the six-month assignment
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