Executive Assistant

Shift5 builds innovative data platforms for onboard operational technology (OT), delivering cybersecurity, predictive maintenance, and compliance solutions for defense and commercial fleets. The Executive Assistant will support multiple senior leaders by streamlining executive operations, managing complex scheduling, and enabling effective communication across the organization. The role focuses on operational efficiency and proactive support in a fast-paced, high-growth environment.

• Manage complex calendars, prioritize engagements, and coordinate scheduling with internal and external stakeholders across the executive team.
• Handle sensitive and confidential information with discretion and sound judgment.
• Coordinate and prepare for onsite engagements, executive visits, and high-profile meetings.
• Manage expense reporting and reconciliation, ensuring accuracy and timeliness.
• Serve as a primary point of contact for internal and external communications, including drafting and refining executive correspondence.
• Anticipate scheduling conflicts, resolve constraints, and oversee domestic and international travel logistics.
• Prepare briefing materials so leaders are equipped for high-impact meetings.
• Track action items, follow-ups, and strategic initiatives across executive forums, including board meetings and leadership offsites.
• Drive process improvements to streamline workflows, enhance organization, and improve cross-functional coordination.
• Maintain structured systems to track priorities, commitments, and strategic initiatives.

• 5+ years of experience supporting C-level or senior executive leaders.
• Proficiency with Expensify, Monday.com, Google Workspace, Slack, and related collaboration tools.
• Strong organizational and prioritization skills in dynamic, high-growth environments.
• Exceptional written and verbal communication skills.
• High level of discretion and professional judgment when handling sensitive information.
• Ability to operate independently, anticipate needs, and support multiple executives simultaneously.
• Experience with travel logistics, expense reporting, and meeting preparation.
• Preferred: experience in defense-tech, SaaS, or startup environments.

• Compensation: competitive base salary range of $90,000 to $120,000 annually; bonus program and equity options.

• Benefits: employer-paid medical, dental, and vision coverage; Health Savings Account with annual employer contributions; life insurance coverage.

• Time off and flexibility: uncapped paid time off; flexible work arrangements and remote work policy.

• Additional perk: tax-deferred public transit benefits via Metro SmartBenefits (DC/MD/VA).