Executive Assistant

Shift5 is a defense-tech and SaaS startup building data platforms for operational technology (OT), delivering cybersecurity, predictive maintenance, and compliance solutions for defense and commercial fleets. The Executive Assistant will support multiple senior leaders by ensuring smooth executive operations through scheduling, coordination, communication, and confidential administrative support. The role helps leaders stay prepared and aligned in a fast-paced, high-growth environment.

• Manage complex and dynamic calendars, prioritize engagements, and coordinate with internal and external stakeholders
• Handle sensitive and confidential information with discretion and sound judgment
• Coordinate and prepare for onsite engagements, executive visits, and high-profile meetings
• Oversee expense reporting, reconciliation, and budget management with accuracy and timeliness
• Draft, review, and refine executive correspondence and communications
• Identify scheduling conflicts, resolve constraints, and manage domestic and international travel arrangements
• Prepare briefing materials to ensure leaders are equipped for strategic and operational meetings
• Track action items, follow-ups, and commitments across forums including board meetings and leadership offsites
• Drive process improvements to streamline workflows, enhance efficiency, and foster cross-functional collaboration
• Maintain structured systems to monitor priorities, strategic initiatives, and operational commitments

• 5+ years of experience supporting C-level or senior executive leaders
• Proven ability to support multiple executives simultaneously
• Proficiency with Expensify, Monday.com, Google Workspace, Slack, and other collaboration tools
• Strong organizational and prioritization skills in dynamic environments
• Exceptional written and verbal communication skills
• High level of discretion and professional judgment
• Ability to operate independently and proactively anticipate needs
• Experience managing complex calendars, travel logistics, and high-profile meetings

• Preferred: experience in defense-tech, SaaS, or high-growth startup environments

• Salary range: $90,000 to $120,000 base (plus bonus program and equity options)
• Flexible and remote work policies
• Employer-paid medical, dental, and vision insurance
• Health Savings Account (HSA) with annual employer contributions
• Life insurance coverage
• Uncapped paid time off policy
• Tax-deferred public transit benefits through Metro SmartBenefits (DC/MD/VA)