Executive/Personal Assistant

SkyePoint Decisions; Virginia (IL); Hybrid; USD 80,000 - 105,000; Full time

Benefits offered by this job

Certification incentive program

PTO

Floating federal holiday options

Health insurance (HMO/HDHP with HSA)

Dental plans

Vision plans

Disability insurance

Life Insurance

401k matched

Job summary

SkyePoint Decisions, centered in Dulles, Virginia, seeks an experienced Executive and Personal Assistant to support the Founder/CEO. This hybrid role requires 2–3 on-site days weekly, coordinating travel, events, and diverse administrative tasks while safeguarding confidential information.

The ideal candidate is highly organized, with strong communication, decision-making, and problem-solving abilities, capable of partnering with senior leadership and managing multiple projects.

Qualifications

• High school diploma and 7+ years as executive/personal assistant with comprehensive support experience.
• Strong organizational, time-management, and prioritization skills under tight deadlines.
• Excellent written and verbal communication and ability to handle confidential information.

Responsibilities

• Coordinate complex executive communications, scheduling, and travel logistics.
• Plan and execute events, board meetings, and high-level meetings with budgets and logistics.
• Prepare presentations, reports, and executive summaries for leadership.
• Serve as liaison between executive team, staff, and external contacts to ensure timely responses.

Skills

Organizational skills

Time management

Attention to detail

Written/verbal communication

Budgeting experience

Interpersonal skills

Discretion with confidential info

Professionalism

Education

High school diploma

Bachelor’s degree (preferred)

Tools

Microsoft Office Suite

Asana (preferred)

Job description

SkyePoint Decisions is a leading Cybersecurity Architecture and Engineering, Critical Infrastructure and Operations, and Applications Development and Maintenance IT service provider headquartered in Dulles, Virginia with operations across the U.S. We provide innovative enterprise-wide solutions as well as targeted services addressing the complex challenges faced by our federal government clients. Our focus is on enabling our clients to deliver their mission most efficiently and effectively – anytime, anywhere, securely. We combine technical expertise, mission awareness, and an empowered workforce to produce meaningful results.

SkyePoint Decisions is looking for a highly organized, experienced Executive and Personal Assistant to support its Founder and CEO. This role provides comprehensive assistance to the CEO and other executives including managing schedules and business/personal logistics, coordinating travel, event planning/execution, and efficiently managing multiple, diverse business and personal projects/initiatives. The ideal candidate will be a detail-oriented, business professional with excellent decision‑making and communication skills who will act as a strategic partner and an innovative problem solver able to anticipate and address the CEO's requirements supporting critical corporate and personal activities.

This hybrid position is based at our Corporate Headquarters in Dulles, Virginia, and typically requires on-site presence 2-3 days per week (Monday, Tuesday, and Thursday). Additional in-office days may be required based on the CEO's schedule and business needs. Candidates must have reliable personal transportation and the ability to travel independently throughout the Northern Virginia, Maryland, and Washington, DC metropolitan area to support business‑related activities and events.

Responsibilities:

• Coordinate and manage complex and diverse executive communications including correspondence, phone calls, scheduling/calendaring, booking/coordinating executive’s business/personal travel logistics, and ensure smooth/flawless execution of a broad range of administrative assignments.
• Professionally handle confidential information with discretion and in compliance with privacy regulations.
• Create and track project management tasks to completion in Asana and ensure assignments align with strategic goals often requiring interaction/collaboration with multiple teams through completion.
• Format, edit, and distribute PowerPoint presentations, Excel reports, and executive summary documents.
• Attend and coordinate the full range of event planning and catering services for a wide range of company and private events such as senior leadership meetings, all‑hands meetings, division and program meetings, customer events, and quarterly Board of Advisors meetings to include site selection/inspections, managing budgets and logistics, coordinating travel and accommodations, preparing meeting materials, note taking, and ensuring efficient handling of all necessary administrative actions for successful event execution.
• Serve as the primary liaison for communications and collaboration between the executive team, associated team members, and external contacts and ensure clear and timely communications, follow‑up, and resolution of inquiries or requests.
• Support corporate facilities management/logistics for CEO work locations (e.g., coordinating vendor appointments, services agreements, property visits, satisfactory performance completion, etc.) and perform reconciliation and substantiation of associated purchases, credit card transactions, vendor deliveries (e.g., gathering receipts, providing purchase details, validating invoice accuracy, ensuring timely payments, and quality delivery of goods/services).
• Provide personal assistance to executive’s family for services and engagements (e.g., book appointments, coordinate travel/logistics, facilitate events, and other miscellaneous activities) and ensure meticulous organization and alignment with the CEO's schedules for timely and professional execution.
• Manage CEO’s service‑provider relationships, adherence to contracted service delivery schedules, and regularly travel to properties for inspections, site repairs, and renovations.
• Handle miscellaneous business and personal tasks as required to support the executive's personal and professional requirements.

Required Qualifications:

• High school diploma, and 7+ years of prior relevant experience as an executive and personal assistant with demonstrated performance providing a comprehensive range of administrative support services for corporate and personal affairs.
• Exceptional organizational and time management skills with proven ability to prioritize tasks effectively and manage multiple tasks and executive assignments with accuracy, timeliness, and professionalism.
• Strong attention to detail, a commitment to professional excellence, and ability to work quickly and accurately under tight deadlines.
• Proficiency in Microsoft Office Suite (Outlook, Word, Excel, PowerPoint, Teams, OneNote, and SharePoint) and other relevant software.
• Excellent written/verbal communication and mathematical skills.
• Experience managing budgets and expenses.
• Strong interpersonal and collaboration skills and the ability to work well with all levels of staff and management.
• Ability to handle sensitive and confidential information with the utmost discretion.
• High level of professionalism and a positive, can‑do attitude.
• U.S. Citizenship required.

Preferred Qualifications:

• Bachelor’s Degree in a relevant field of study.
• Knowledge and prior utilization of Asana collaboration and efficiency software.

Compensation:

Salary Range: $80,000 - $105,000

The SkyePoint Decisions salary range for this position is a general guideline only. It represents an estimated range for this position and is just one piece of our total compensation package.

Salary at SkyePoint is determined by various factors, including but not limited to location, work schedule, the candidate’s combination of education, knowledge, skills, competencies, and experience, as well as contract‑specific affordability, market data and business considerations.

In addition to a competitive salary, SkyePoint offers benefits including a certification incentive program, PTO, floating federal holiday options, several insurance options including HMO and High Deductible plans with Health Savings Accounts [HSAs], Flex Spending Accounts [FSAs], Full Dental Plans, Vision, ST/LT Disability, Life Insurance, and 401k matched.

What We Can Offer You:

• At SkyePoint, we go B.I.G. (beginning in GRATITUDE) by recognizing all we have and giving back to our employees, families, and communities. It instills a positive mindset that permeates all we do. By beginning in gratitude, SkyePoint can continue to spread living in gratitude each day.
• Great Benefits: Several insurance options including HMO and High Deductible plans with Health Savings Accounts [HSAs], Flex Spending Accounts [FSAs], Full Dental Plans, ST/LT Disability, Life Insurance, floating federal holiday options, and 401k matched
• Certificate Incentive Program: To promote professional development, we recognize and reward employees who obtain new certifications aligned with business needs.
• Flexible Work Environment

SkyePoint Decisions is an established ISO 9001:2015 and ISO/IEC 27001:2013 certified small business and appraised at CMMI Level 3 for Services and Development. We possess a common vision of excellence and foster a collaborative team culture built upon individual performance and accountability. We invest in our people and systems to create value for our clients. It is the SkyePoint Way. We are grateful for the opportunity to work with exceptional people and give back to the communities we serve. Our employees value the flexibility at SkyePoint that allows them to balance quality work and their personal lives.

SkyePoint Decisions is a participating E-Verify Employer.

U.S. Citizenship is required for most positions.

Equal Opportunity Employer/Veterans/Disabled.

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