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Executive Assistant

Middleburg, VA

Sandboxx is the leading platform dedicated to finding and building technology solutions throughout a service member's military life cycle. We're looking for people with drive and initiative who are excited about making great technology and a positive attitude for our service members.  Come help us build meaningful solutions for the military community!

Executive Assistant

Location: Middleburg, VA

Type: Full-time

Sandboxx is seeking a highly organized, proactive, and emotionally intelligent Executive Assistant to support our executive team, while also driving critical cross-functional initiatives. You’ll blend traditional EA responsibilities with high-level strategic execution, similar to a Chief of Staff role.

This role is ideal for someone who thrives in ambiguity, enjoys solving problems before they appear, and wants to contribute meaningfully to the mission and momentum of a growing company.

What You’ll Do

  • Manage calendars, prioritize meetings, and coordinate logistics across multiple time zones with speed and precision.
  • Own inbox triage, follow-ups, and delegation routing to ensure executive focus is protected.
  • Act as a gatekeeper and a gateway—building trust with internal and external stakeholders.
  • Prepare briefing documents, internal memos, board materials, and follow-up tasks to keep initiatives moving forward.
  • Lead or support special projects across hiring, operations, fundraising, or product—acting as a force multiplier for executives.
  • Anticipate needs and proactively solve problems before they’re visible to others.
  • Liaise across departments to streamline workflows, surface blockers, and bring clarity to chaos.
  • Support leadership’s external presence (e.g., LinkedIn, speaking engagements, investor updates).
  • Plan and coordinate company events, retreats, offsites, and travel with attention to detail and cultural context.
  • Handle confidential information with discretion and integrity.

About You

  • 5+ years of experience supporting senior executives, founders, or in operations roles. Chief of Staff, strategy, or high-performance EA experience preferred.
  • Deep understanding of startup dynamics and the pressures facing founders and leadership teams.
  • Exceptional written and verbal communication skills—especially with asynchronous documentation and follow-through.
  • Strong project management instincts with the ability to prioritize ruthlessly and execute reliably.
  • Highly emotionally intelligent: you read the room, intuit needs, and handle sensitive situations with grace.
  • Systems thinker who enjoys improving processes, eliminating friction, and bringing order to ambiguity.
  • Comfortable with tools like Google Workspace, Notion, Slack, Zoom, and project management tools (e.g., Asana, Linear, Trello).
  • A blend of humility and confidence—you’re not afraid to ask questions, challenge assumptions, or push back when needed.
  • Mission-aligned: you believe in the power of service, connection, and building for impact.

Benefits & Perks

  • Competitive salary + equity options
  • 100% company-paid health, dental, and vision (employee-only plans)
  • 401(k) with company match
  • Unlimited PTO + 11 company holidays + year-end holiday break
  • 12 weeks paid parental leave for all parents
  • $1,500/year learning & development budget
  • $1,000/year wellness stipend
  • Mission-driven team, startup autonomy, and the opportunity to improve lives in the military community

At Sandboxx, we believe technology should serve people—not replace them.

Come help us shape the future of how service members stay connected, informed, and empowered—while building with the tools of tomorrow.

Sandboxx is an equal opportunity employer - if you are a continuous learner who enjoys startups in either tech or military, you'll thrive at Sandboxx.  We are committed to building a diverse and inclusive workforce and take affirmative action to not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, sexual orientation, veteran or military status, or any other legally protected characteristics.  This policy applies to all employment practices within our organization, including but not limited to recruiting, hiring, promotion, termination, compensation, benefits, and training.  Sandboxx is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process. 

To all recruitment agencies: Sandboxx does not accept agency resumes.  Please do not forward resumes to our jobs alias, Sandboxx employees, or any other organization location.  Sandboxx is not responsible for any fees related to unsolicited resumes.  

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